Carol Wayne used her popularity to become one of the most adored talk show sidekicks in television history. Though she appeared in several television shows and movies, her best-known gig was that of the ditzy Matinee Lady on “The Tonight Show”‘s Art Fern Tea Time Movie sketches. Wayne appeared in over 100 shows during a thirteen-year run.
Unfortunately, when the show was cut to an hour, Wayne’s role declined, sending her through a downward spiral. Wayne found herself making bad business choices, dealing with addiction, and getting herself into a lot of financial trouble. She was such a talented individual.
Madonna
Madonna, dubbed the "Queen of Pop," was the kind of celebrity who drew everyone's attention, especially in the late '80s. On June 9th, 1987, Madonna made her first appearance on "The Tonight Show" with Johnny Carson. Though many thought the Material Girl's debut would be like any other guest on his popular late-night show, they were wrong.
Madonna had a plan in mind, something that soon became evident to the fans at home. Madonna had a mission; throughout the show, she flirted with Carson, flirting to the point that was hard to ignore. A few months after the interview aired, Madonna traveled the world to promote her "Who's That Girl" album. Coincidence? We think not.
Raquel Welch
Even if you're the most professional, straight-to-the-point talk show host, you know you're in for a good time when Raquel Welch was the interviewee. With her stunning outfits, Colgate smile, and beautiful tan, Welch managed to make the uptight Dick Cavett seem a little more easygoing.
The actress had a long list of television and movie roles under her belt, but her big break happened when she appeared in "One Million Years B.C." She wore nothing but a deerskin bikini, immediately becoming a worldwide sensation. She continued her career as an actress, singer, and model and is remembered as one of the most beautiful stars in film history. In early 2023 she sadly passed away.
Janis Joplin
Janis Joplin has become one of the most influential musicians of all time, and unfortunately, one of the earlier members of the 27 Club. Her appearance at Woodstock was nothing short of iconic and her impact on rock music is unquestionable. A few months before her tragic passing, Joplin made one of her many appearances on "The Dick Cavett Show."
Sadly, on August 3rd, 1970, Joplin gave her final interview and televised appearance on the show, performing "Half Moon" and "My Baby." Known for her powerful mezzo-soprano voice and electric stage presence, the talented musician, would tragically lose her life on October 4th.
Adrienne Barbeau
Two weeks before Christmas 1974, the beautiful 27-year-old actress Adrienne Barbeau appeared on "The Tonight Show." Seeing as it was just a couple of weeks before Christmas, Carson and Barbeau naturally started talking about gifts. The young actress shocked the late-night host and audiences at home by revealing that she had received many interesting gifts from lovers over the years.
These gifts included a set of encyclopedias, car repair items, and a fire extinguisher. Being the true talk-show host, Carson pointed out the "multiple lovers" comment, but Barbeau refrained from disclosing any personal details. We imagine she wanted to "escape from LA" immediately.
Donna Summer
When Donna Summer appeared on "The Tonight Show" on November 28th, 1979, she came with a message. Anything men can do, women can do as well. She was a fan of Johnny Carson as a child, and the "Queen of Disco" made sure that not only was she musically and theatrically talented, but she also made sure that Carson and the fans at home knew of her other skills.
Carson remarked that Summer was mechanically talented, with the ability to fix cars, and made a rather politically incorrect comment about girls not being mechanically inclined. That's when Summer put Carson in his place, as she should!
Zsa Zsa Gabor
Thanks to Johnny Carson and Zsa Zsa Gabor, Twister became a household favorite. When the "Moulin Rouge" actress made an appearance in 1966, the two spent the entire episode playing the game. It was released earlier that year, and it was expected that the Milton Bradley game would blow up.
Unfortunately, upon its release, it was not as popular as expected. Thanks in large part to seeing the two celebrities creatively play together, Twister sales skyrocketed with over 3 million in the following few months! Now that is definitely one way to make a game's popularity sore through the roof!
Doris Day
Doris Day, the multi-faceted singer and actress, made an appearance on "The Tonight Show" in 1974. Not only did Day use the show as a platform to show off the long list of men she starred alongside (James Garner and Clark Gable, to name a few), but she discussed her role as an animal welfare activist.
In addition to her on-screen success, Day was also an accomplished singer. Her most memorable songs included "Sentimental Journey" and "My Dreams Are Getting Better All the Time." Truth be told, there was nothing particularly awkward about this interview. Doris Day is just impossible to ignore.
Cassandra Peterson
As one of the more prominent guest hosts of "The Tonight Show," Joan Rivers welcomed many esteemed guests. During her stint on the Halloween night episode in 1985, Rivers welcomed the Mistress of the Dark, Elvira.
She was known for her exposing attire, which made Peterson the envy of Rivers for most of the night's episode. The original and perhaps the most famed goth girl, Elvira was Peterson's sexy vampire alter ego. Elvira was featured in film, television, and comic books throughout the '80s. Is it just us, or is Cassandra giving off some real Bride of Frankenstein/Morticia Addams vibes?
Ann Margret
It comes as no surprise that often, actors and actresses get typecast into roles they may or may not genuinely enjoy. In the case of Ann Margret, to fans, she was labeled no more than a "B" movie actress, which was solely based on her early movie roles. On February 29th, 1972, she was a guest on Johnny Carson's couch.
During their conversation, Margret talked about being taken seriously as an actress. She had five Golden Globe awards to her name, along with several Golden Globe, Academy Awards, and Emmy nominations! She got a chance to fix her reputation with her appearance in "Carnal Knowledge," alongside Jack Nicholson, a role that would show audiences a more genuine side of her acting skills.
Susan Anton
There was not a room Susan Anton couldn't light up, "The Merv Griffin Show" was no different. When David Brenner welcomed the actress, she stole the show. And it's not hard to see why. Anton was known for her roles in several Muriel Cigar commercials.
She was known for pushing products on television, radio, and print. She would go on to make many appearances on "The Merv Griffin Show," and though she never had a big breakout role on-screen, she was a popular choice when it came to guest appearances. She made her way onto many successful shows, including "Baywatch" and "The Love Boat."
Carol Wayne
Carol Wayne used her popularity to become one of the most adored talk show sidekicks in television history. Though she appeared in several television shows and movies, her best-known gig was that of the ditzy Matinee Lady on "The Tonight Show"'s Art Fern Tea Time Movie sketches. Wayne appeared in over 100 shows during a thirteen-year run.
Unfortunately, when the show was cut to an hour, Wayne's role declined, sending her through a downward spiral. Wayne found herself making bad business choices, dealing with addiction, and getting herself into a lot of financial trouble. She was such a talented individual.
Whitney Houston
One of the most famous names and voices of our time, Whitney Houston, is one of the best-selling female artists of all time. She's sold over 200 million albums worldwide and is the bestowed female singer to date. She was no stranger to celebrity chat shows and this image was from one of the very best.
In 1990 Jay Leno had the pleasure of congratulating the singer on breaking the Beatles' long-standing record of number-one hits. During her memorable interview on "The Tonight Show," she took both the live studio audiences and the audiences at home breaths away when she performed "I'm Your Baby Tonight."
Yvonne Craig
When we say Yvonne Craig, you probably hear "Batgirl," don't you? Synonymous with the superhero, Craig had no choice but to appear in full costume and character on "The Merv Griffin Show" on September 5th, 1967. Not breaking character, Craig used her interview to advocate for women's rights, putting an emphasis on equal pay.
In one commercial, Batman and Robin were in need of saving, but Batgirl refused to release them. This was an act of protest, seeing as Craig was paid less than Robin. Throughout her career, Yvonne Craig was a symbol of female empowerment and remained one to this day.
Judy Landers
Celebrities meeting their celebrity crushes is pretty meta if you ask us. When Judy Landers made an appearance on "The Tonight Show" in 1979, she disclosed that meeting him was a dream come true. The reason? She had a crush on Carson. Now would you believe that?
Landers was in the midst of her time as Stacks from "BJ and the Bear" when she sat down for an interview with the late-night host. When questioned about her ability to drive a semi-truck, Landers answered confidently, letting the host and audiences know she could drive a big rig. What a cool gal!
Diane Lane
When Diane Lane appeared on "The Tonight Show," she had just turned 18. She was on the segment promoting the film adaptation of "Rumble Fish" and, after being introduced, would not kiss Carson on the cheek. Seriously, do you blame her for declining?
Seeing as he was forty years older than her at the time, her decision seemed pretty justifiable. When Carson asked Lane what she had done to celebrate her 18th birthday, she noted that she had spent most of the day doing laundry. Knowing Carson's long history of innuendoes, we're guessing he was looking for something a little juicier.
Farrah Fawcett
We will forever remember the long hours spent in the mirror, trying to perfect the Farrah Fawcett look. She had many roles in both television and film throughout the years but will forever be remembered as Jill Munroe in "Charlie's Angels." It's hard not to remember the poster of her in that red bathing suit.
Shortly after her decision to leave her one-year stint as Munroe, Fawcett was a guest on "The Tonight Show." During their conversation, talk of the show rating's rapid increase became a hot subject. Fawcett linked the success to the lack of the cast wearing bras.
Robyn Hilton
Like many of the actresses before and after her, Robyn Hilton put Johnny Carson in his place. In her 1974 interview, one that was meant to focus on the upcoming release of the comedy classic "Blazing Saddles," Hilton was subject to several offensive questions about her career.
Carson believed that Hilton's acting career was built from being a beauty pageant contestant. Her quick and cut-to-the-point response was that she "didn't believe in beauty pageants." Now that's one way to shake up the culture and show how progressive you are. She was so ahead of her time and paved the way for many forward thinkers!
Jayne Kennedy
Jayne Kennedy was one of the first of her kind. The multi-talented star broke gender barriers, but she broke racial barriers as well. She was an actress, dancer, pageant winner, model, sports broadcaster, and television personality and showed the world that women could be just as successful as men, if not more!
Along with her three-year stint on "The Dean Martin Show," Kennedy became one of the first female NFL announcers as the host of "Greatest Sports Legends." Kennedy has done so much in recent times but did celebrate her 35th wedding anniversary in 2020 with her husband, Bill Overton.
Marlo Thomas
According to Marlo Thomas, it was "love at first sight" when she met daytime talk show host Phil Donahue. That being said, it took the couple three years before they got married. The actress and activist appeared on her future partner's show in 1970, and the chemistry between the two was evident to all.
Before the end of the segment, Donahue let his guest know how much he enjoyed her company. Thomas responded that whoever the woman in his life is is a lucky lady. Who would have thought that Thomas would soon be that lucky lady? It's a match made in heaven!
Connie Stevens
Connie Stevens, best known as "Cricket," in the detective series "Hawaiian Eye," was also a singer. She recorded a number of singles and albums, including one of her most famous songs, "Sixteen Reasons." Though she made a name for herself in the US, she was even more popular overseas. How on earth is that even possible?
She knew that even though she didn't have only one big thing going for her, she had created something people loved. In 1975, she got the chance to connect with the North American audience when she appeared on "The Tonight Show." What a legend.
Goldie Hawn
Goldie Hawn captured everyone's attention with her big blue eyes. She was a guest on the show soon after winning an Academy Award for Best Supporting Actress, and she was on her way to becoming an international star. Her smile and laugh were both contagious; she was just at the start of her decades-long career.
Hawn is now an award-winning actress and producer, proving the world wrong when they dubbed her the stereotypical dumb blonde. And since then, she has formed quite the power couple with Kurt Russell and brought some wonderful actors into the world, including Kate Hudson and Wyatt Russell.
Dolly Parton
Johnny Carson was known for his no-filter approach, which often made many guests uncomfortable. "The Tonight Show" host often took things too far and acted inappropriately during many interviews he had with the wonderful Dolly Parton. After all, "Johnny Carson and Dolly Parton" does have a nice ring to it.
At any rate, the award-winning country singer continued to make appearances on the show. Carson would spend more time discussing her physical attributes than focusing on her true talents and abilities on stage and screen. We just love seeing two very different icons in the same photo. And that's what we got here.
Loni Anderson
Despite his controversial nature, Johnny Carson still managed to host the most beautiful women in Tinsel Town on his show. During the late 70s and 80s, Loni Anderson fit the role of the stunning blonde to catch everyone's eye. And naturally, she would find her way on Johnny's show.
She was one of the most attractive actresses of her time, and when she was hired for "WKRP in Cincinnati," producers admitted she was hired for her looks, not her talent. She reminded them of a mix between Marilyn Monroe and Jayne Mansfield. But it was soon clear that there was a lot more to her than just looks. She also had the charisma and acting chops to boot.
Shari Belafonte
Although she stands in her own right as a model, singer, and actress, Shari Belafonte was still better known as the daughter of Harry Belafonte than she was for her own accomplishments. That's likely to happen. After all, Harry Belafonte was a really big deal, for a really long time.
Before her role in the popular series, "Hotel," Shari worked mostly behind the camera as a production assistant and publicist. After her popularity increased, she appeared on "The Merv Griffin Show." Though she never outshined her father, she continues to act and has been in countless films and television shows.
Sonny & Cher
As their hit single "I Got You, Babe" blew up, the husband and wife duo of Sonny and Cher made their way through the television talk show circuit. One of those appearances was on "The Merv Griffin Show" in 1969, which was a really beautiful sight for everyone involved.
Though their music was a fan favorite, they also appealed to fans with their undeniable love for each other, their dance moves, and their choice of clothing. Sonny and Cher even had their own variety television show called Cher Comedy Hour”, which ran from 1971-1974. Of course, Cher has had a full, illustrious career by herself. But oh, these were the days.
Charo
She was born Maria del Rosario Mercedes Pilar Martinez Molina Baeza, but everyone knew her as Charo. She was a talk-show regular, having made multiple visits on "The Tonight Show," "The Merv Griffin Show," and "The Mike Douglas Show." Charo was a talented actress, singer, and comedian, amongst many other natural talents.
Though she struggled with fluent English, the Spanish superstar used her irresistible personality to appeal to English-speaking audiences and soon became a household name with her "cuchi, cuchi" catchphrase. She was so endearing and would cast a spell on all who interviewed her, as you can see here.
The Time of Your Life
Long before "Friends" or "How I Met Your Mother," there was "The Time of Your Life." With a regular cast of characters, the short-lived show had their characters meet up at their regular hangout spot each week, observing and interacting with others. It was a really beloved show that TV viewers couldn't get enough of.
Stars like Jackie Gleason and Betsy Palmer were the focal points of the show, as Gleason's character, Joe, evaluated the true spirit of each newcomer to their spot. And of course, the stars of the show had many noteworthy appearances on the most popular TV chat shows of the era.
Cher
Surprisingly enough, in 1979, Cher took over as the co-host of "The Mike Douglas Show" for a week-long gig. The diva was able to show off her novel fashion taste but also had an opportunity to perform several of her hit songs. Seriously, who was not going to tune in to that?!
She sang "My Song," Take Me Home," and "Happy Was The Day We Met," to name a few. Cher had a goal in co-hosting the show; she wanted to prove to fans and the world that she was more than just a sidekick to Sonny, and she did!
Deana Martin & Tina Sinatra
There is something so charming about seeing experienced, seasoned celebrities performing with their children. It just goes to show how the apple doesn't fall far from the tree. "The Dean Martin Show" had many extraordinary guests, but nothing topped off the segment in which the nineteen-year-old daughters and their fathers appeared on the show.
In 1967, Frank Sinatra and Dean Martin were joined by their daughters Tina and Deana for a rendition of "Do-Re-Mi," from "The Sound of Music." As a late-night fan favorite, the variety show welcomed several performers and guests over a nine-year span. But this was right up there with the very best.
Joey Heatherton
Joey Heatherton was everywhere in the 1960s and 70s. Whether she was on stage or on screen, many considered the talented starlet's performances shocking. Of course, that would not scare Johnny Carson away, and he invited the star onto his show in 1963 to teach him how to dance.
Response to the show was so positive that Heatherton was invited to the inaugural episode of "The Dean Martin Show" a year later. But in this photo, we see Heatherton enjoying herself with host Jack Jones and the one and only, Tom Jones! It does not get much bigger than that!
Dean Martin
Jerry Lewis was the king of comedy. Dean Martin, on the other hand, was "The King of Cool." They complimented each other well, and the two legendary performers created one of the most memorable comedy duos of all time.
A member of the "Rat Pack," Martin was the host of "The Dean Martin Celebrity Roast" and "The Dean Martin Show." Highlighted by one of Martin’s biggest hits, “Everybody Love Somebody,” his show ran off 264 episodes over the course of nine years. Here, we can see Martin, Lewis, and Sinatra having a moment together, and it's really playing on our heartstrings.
Elke Sommers
Not only did Elke Sommers make multiple appearances on various late-night shows, but she also co-hosted one as well! The beautiful German actress co-hosted "The Mike Douglas Show" during the week of February 7-11, 1972. And boy, she certainly did not disappoint by any stretch of the imagination.
Elke has 100 television and film roles under her belt and made a name for herself after fleeing Germany during World War II. She would move to Hollywood in the 1960s and started working on the big and small screen. She might be one of the European country's finest exports, behind Adidas and Volkswagen.
Grace Slick
Who would have thought that the lead singer of Jefferson Airplane would be the first person to use the "F" word on television? When Slick and the band appeared on "The Dick Cavett Show" in 1969, it was the day that sent television censors into full panic. It finally happened, and a celebrity dropped the F-bomb out of nowhere!
They performed their hit song "We Can Be Together," which features the famous four-letter word. Slick's vocals shocked Cavett, the live audience, and viewers around the globe. The incident led to increased censorship on television, and things would never be the same after that.
Jean Shrimpton
Becoming an "it girl" is no joke; it's given for a good reason. Shrimpton was charming, engaging, and entertaining - the perfect it girl. She was one of the most famous females in the 1960s; the British model and actress was a sight to be seen.
When she wasn't on the runway, on-screen, or in advertisements, Shrimpton was a guest on many of the late-night talk shows. Clearly, this was one host that couldn't quite catch his breath when he experienced the looks and charisma of Jean Shrimpton. We just love the vibes going on in this photo; it looks like everyone was having such a good time.
Judy Garland
In 1962 Judy Garland joined Jack Parr on stage for an interview on "The Tonight Show." The two had a very candid and humorous interview. Garland talked about her childhood and the early years of her career. The famed actress was born Frances Gumm and started off as a performer with her two sisters.
Before her iconic performance in "The Wizard of Oz," the young actress would spend time perfecting her talent alongside Mickey Rooney, Liz Taylor, and more. You have to work hard to make it in Hollywood, and boy, did Garland work! Her daughter was also a star!
Jack Douglas & Reiko
Best known as a writer for some of the biggest names in the business, he was the one and only Jack Douglas. Douglas's third wife, Reiko, was a regular on the talk show circuit in the 60s and 70s. She capitalized on America's attraction to anything and everything that was foreign and exotic.
Though she spoke fluent English, the Japanese-born beauty pretended to know minimal English, wearing traditional Japanese clothing. It was an interesting sight to be seen and actually made a lot of viewers in the crowd and on TV laugh in equal measure. They were a match made in heaven.
Dionne Warwick
This next statistic is outstanding. With 69 songs on the Billboard Top 100 for over thirty years, Warwick is second to Aretha Franklin as the most-charted female singer of all time. Along with her award-winning hits, Warwick had plenty of collaborations with big names.
When she made her appearance on "The Dean Martin Show," she decided against performing one of her songs. Instead, she showed her other talent, acting, as she performed a comedy skit alongside Dean Martin. Not many singers have been able to do it better than Dionne Warwick. If there are, there are only a select few.
Zsa Zsa Gabor
Five years after Zsa Zsa Gabor was crowned Miss Hungary, she moved to the United States. Her European elegance and unique style would help ensure she became a sought-after actress. Naturally, she became heavily typecast and would find a variety of roles working on stage, television, and of course, the big screen.
She soon became a frequent guest on late-night talk shows, and of course, found her way into tabloid magazines. Gabor was known for her extravagant lifestyle and many relationships. In fact, she was married a total of nine times! That is a pretty remarkable statistic, even by Hollywood standards!
Joan Crawford
Joan Crawford was undoubtedly one of the most popular actresses in the 60s. She appeared on "The Merv Griffin Show" after her performance in the psychological thriller, “Whatever Happened to Baby Jane?” Crawford received a standing ovation from the fans in the audience. And that was just the tip of the iceberg in terms of her impact on Hollywood.
Interestingly enough, though the award-winning actress was a fan favorite, this was far from the truth when it came to her castmates. A truth that was revealed in the tell-all book, "Mommie Dearest." Actors having beef with each other is by no means new in Hollywood, but Joan Crawford attracted a lot of drama in her career.
Bette Midler
In his final show, Johnny Carson welcomed Robin Williams and Bette Midler as his featured guests on May 21st, 1992. A memorable night in which Carson had guests join in, Midler made it all the more memorable. It was an emotional night for all, and Midler serenaded the man of the hour with a number of songs.
Carson's final "The Tonight Show" segment was so captivating; it would go on to win an Emmy Award. And let's face it: when you have the incredible talent of Better Midler and Robin Williams at your disposal for your final episode, it is bound to rake in the viewers and be an emotional climax.
Joan Rivers
Often, talk-show hosts and comedians say something so often; they become synonymous with it. For Joan Rivers, that was: "Can we talk?" The line originated from her time as a stand-up comedian; Rivers used it instead of saying, "Let's be honest." And can we talk? There was nothing about Joan Rivers that wasn't iconic.
She navigated her way to the comedic roots of topics that seemed hard to discuss. Truth be told, the late-night show host didn't even realize she was saying it so much until her audiences started repeating it back to her! Can we talk? There have been better catchphrases in the world of TV.
Elizabeth Taylor
The name and the legend, Elizabeth Taylor, was one of the most popular leading ladies in Hollywood, bringing in box office numbers. It may seem like it was always fame and fortune for Taylor, but for a period of time, Taylor considered walking away from it all.
That was when she was offered a role in the star-studded cast of "Giant." She played alongside James Dean, Dennis Hopper, and Rock Hudson. As an actress and philanthropist, Taylor would often appear on late-night talk shows, including many visits with Johnny Carson. And boy, she had plenty of juicy things to talk about, including her many marriages.
Jill Corey
Jill Corey's story isn't your typical "rise to fame" story. She found success as a teenager singing on a live radio show in her hometown of Avonmore, Pennsylvania. She found a record deal with a recording company and created several hit singles and records in the early 1950s.
In addition to her many stage performances, the young woman was also featured on a number of radio and television shows, including, you guessed it, "The Tonight Show," with Johnny Carson. Corey had a creative style of singing, dancing, and a selection of outfits. Her unique taste and girl-next-door demeanor made her a fan favorite.
Joan Crawford
As the third host of "The Tonight Show," Johnny Carson officially took over the interviewing desk on October 1st, 1962. For the next thirty years, Carson welcomed the biggest names in Hollywood. On his very first night, Joan Crawford was honored as his featured guest.
Receiving awards for her role in the psycho-thriller, “What Ever Happened to Baby Jane?" Joan would still be resentful towards her co-star, Bette Davis, who was nominated for several awards for her performance in the film, while Crawford was not. Their rivalry was so iconic that they even made a miniseries about it! Now that's saying something.
Engelbert Humperdinck
It almost never happens that a singer has three chart-topping hits in a single year, but for Engelbert Humperdinck, 1976 was a year to remember. His three hit songs took over both the United Kingdom's and North America's music charts. He really was the talk of the town around this time.
Humperdinck was nominated for a Grammy and was named the "most played jukebox record of the year." Of course, with fame comes promotion, and Humperdinck made the rounds on the talk shows, including "The Tonight Show" and "The Dean Martin Show." Johnny Carson could not get enough of him!
Elvis Presley
The original host of "The Tonight Show," Steve Allen, returned to guest host the show in 1961. He welcomed "The King of Rock and Roll" to the segment. Recently released from his commitment to the military, Elvis Presley came on stage to perform his hit, "Hound Dog."
Elvis was excited to return to the stage and return to entertaining. Serving in the army forced Presley to take a break from the limelight, which ironically increased his popularity. His absence made fans excited when he returned, and he ultimately became bigger than ever before. But in this photo, we see peak Elvis.
Errol Flynn
As one of the biggest stars of the 1930s, Flynn was one of Hollywood's biggest stars. In the prime of his career, he was romantically linked with a number of female stars, including Carole Lombard, Lupe Valex, and Marlene Dietrich, to name a few.
The "The Adventures of Robin Hood" actor was no stranger to making promotional appearances on many popular late-night talk shows. This photo was taken when Steve Allen left "The Tonight Show," and Jack Paar was in the middle of his five-year tenure. During this time, a much more diverse range of stars would guest-appear on the show.
Jay Leno
Before he has his own show, David Letterman would occasionally act as a guest host for "The Tonight Show," between 1978-1980. In 1982, Letterman would spread his wings on his own show, "Late Night with David Letterman." Ironically enough, Letterman welcomed future "Tonight Show" host Jay Leno as a guest.
At the time, Leno was a regular on the stand-up comedy circuit, slowly transitioning to a number of minor roles in film and television. As Carson retired in 1992, fans were sure Letterman was next in line to take over "The Tonight Show," yet lo and behold, the role when to Leno, who hosted until 2009!
Emma Watson
The most awkward moment on late night television that Emma Watson ever experienced happened on Jimmy Fallon’s show back in 2012. She joined him at the desk and broke in with a compliment on the ‘Halloween candy thing.’
The Halloween candy thing is a skit performed by late-night show fans who taped their children’s reactions when it was explained to them their parents had eaten all their candy. It was very brutal and very funny; Leno dissed it for cruelty. But Watson apparently loved it. Unfortunately, Jimmy Kimmel’s show did that bit, and Watson was facing Jimmy Fallon, absolutely mortified.
Nicole Kidman
Nicole Kidman visited Jimmy Fallon on " The Tonight Show" in 2015. The last time they met was on a 2002 date. Yes, you read that correctly; Fallon was set up on a date with the A-lister bombshell. A mutual friend brought her over to Fallon’s place. Kidman and Tom Cruise were on the splits at the time. Fallon didn’t know that either.
He never knew it was an actual date. She explained that she wasn’t interested because he ignored her and played video games. Then she speculated that Fallon didn’t like women. Fully mortified, Jimmy briefly walked off his own show.
Robin Williams
Robin Williams is epic in every interview he ever gave. In 1998 he was on key with David Letterman. Letterman quizzed him about his friendship with sitting President Bill Clinton, and the exchange was hilarious.
When it got to the point of his visit to promote "Good Will Hunting," Williams spoke of the film endearingly; he clearly loved the project. “I got this amazing script, I agreed to do it, and then, all the sudden, I meet [Ben Affleck and Matt Damon] on the set.” Then unknowns, Williams joked about asking to see their ID and if they had their father’s permission.
Drew Barrymore
Recently, Drew Barrymore admitted that her performance on David Letterman’s show in 1995 was a TMI moment that she had learned from. She was 20 and had already been in the entertainment industry for more than a decade. She said she didn’t regret it because it was fun, but here’s what happened.
Barrymore asks Letterman if he’d like her to table dance for him. Paul Shaffer provided some bluesy music. Just before her dance on his desk ends, she flashes him really quickly and returns to her seat. Letterman meant it when he said, “I can’t thank you enough for that.”
Will Smith
Graham Norton gives Will Smith and his son Jaden Smith mics, and they bust into some rhymes. Lighting up "The Graham Norton Show," Smith doesn’t stop there. Oh no. It turns out the "Men in Black" actor also brought his personal DJ, Jazzy Jeff, to the program.
Next, he and Jaden perform " The Fresh Prince of Bel-Air" rap. Meanwhile, guest Heather Graham is dancing and swaying along. Will Smith’s biggest surprise happens when Alfonso Ribeiro jumps on stage to do his trademark Carlton Dance. Even Norton hops on stage to get into the dancing fun. A great time was had by all.
Chris Pratt
When Chris Pratt appeared on "The Graham Norton Show," the host could not help but ask Pratt about one thing in particular: getting naked. Immediately, the actor, there to promote "Guardians of the Galaxy," jumped into his naked stories.
Apparently, Pratt has always enjoyed shocking people by undressing, especially as a kid when he got in trouble for it often. When he pulled the prank to get a good shot of a scene at "Parks and Recreation," his flashing days came to an abrupt end. According to NBC, he must never do that again. And in fact, he framed the letter.
Justin Bieber
This was a long time ago, Bieber time. Justin sported only two tattoos. The second one was still healing. This became clear when Bieber screamed as David Letterman grabbed the young artist’s arm to admonish him about getting any more tattoos. “Believe,” the name of his new album was printed across his forearm.
Meanwhile, David Letterman, interviewing the 18-year-old in 2012, gave fatherly advice — go to college, don’t get any more tattoos, and vote in US elections (even though he’s Canadian). By our count, he didn't listen to Uncle David at all. However, it's never too late, especially for this young man.
Billie Eilish
Right off the bat, Billie Eilish calls Jimmy Fallon out. She remembers seeing him on TV when she was a kid. He was singing songs and dancing on "The Electric Company." Fallon is mortified. But then they get into a story from her childhood.
Comedian Colin Quinn joins them for The Tonight Show's “True Confessions” game. She grosses them both out. Eilish talked about her Where Do We Go world tour. The astounding 17-year-old also revealed which songs she would sing on SNL. It's amazing to think how far Billie Eilish has come since then, with all of those platinum records and Grammy Awards under her belt.
Russell Brand
Russell Brand, obnoxious, always on brand, has a way of getting under peoples' skin, and this includes his fellow celebrities. He gnawed into Emily Blunt’s story about swimming with dolphins on " The Graham Norton Show" and wouldn’t let go. She was describing a close encounter she had with a 6-foot-long shark. Brand breaks in dismissively. “It’s just a type of fish.”
Blunt, frustrated, tells him to stop diminishing her story. “I went near a fish,” he doesn’t stop. Interrupting her again, laughing, he continues mocking her, “I was near a fish once.” Fair is fair once we find out that she embarrassed Brand backstage by ridiculing his Velcro belt.
Sofia Vergara
Sofia Vergara gets totally creeped out in the hot seat next to Conan. She visited the Conan O’Brien show in 2014. The talk show host made her uncomfortable as soon as she sat down. In the creepiest voice he could conjure, Conan says, “I love you.” Sofia casually tries to brush it off, “Don’t be creepy,” yet she’s clearly disturbed.
As the interview goes on, it only gets creepier. Conan tells her he enjoys dancing with her boyfriend. “Now it’s really getting creepy,” she says. Next, Conan begs her to laugh at his joke. All she can say is, “Creeeepy.”
Mark Ruffalo
They were discussing fears on BBC One’s "The Graham Norton Show" one evening in 2015. Comedian Josh Widdicombe, having just divulged that he used to write for "Dora the Explorer" magazine, was not ready for the insult that would be slung at him. It was Widdicombe’s turn to share a personal fear.
He started to say he was going to go with flying. But then Mark Ruffalo rudely suggested Widdicombe might fear girls under the age of 12. The actor clearly regretted it and walked off the stage in shame after trying to apologize to Widdicombe with a chivalrous handshake.
Aziz Ansari
"Parks and Recreation" star Aziz Ansari has been through a lot over the last decade. Many ups and downs, if we do say so ourselves. Here, he visited " The Late Show" and dug right in by calling CBS, in so many words, racist. He also pointed out that Stephen Colbert is the “bagillionth” white guy on TV.
Colbert, dumbfounded, sat shifting in his chair, fretting, it would seem, CBS knocking on his door. Still tense, Aziz quipped that someone is going to get fired for misquoting the title of his book. But Colbert broke the tension with a joke. Laughing, he said that he hopes it was a white guy.
Jaime Fox
Jamie Foxx visited "The Graham Norton Show" in 2017. He managed to give an epic stand-up routine while sitting on the red couch with Judi Dench, Steve Carrell, and Kristen Wiig. Talking about the travails of dating at 49, he describes standing outside a club in LA.
A carload of starstruck young women screams, “OMG, it’s Jaime Foxx!” Foxx smiles, “What’s up?!” It turns out they go to school with his daughter. Another time when he was a DJ at a club, three twentysomething young ladies found out he was 49. He said they acted as if he told them he had a terminal disease!
Justin Timberlake
If you didn’t know Justin Timberlake and Jimmy Fallon are in a BFF bromance, now you do. They have one of the most adorable friendships of all the celebrities. On "The Tonight Show," Timberlake and Fallon do an SNL-like skit.
Dressed up as 13-year-olds at summer camp, the buddies get in trouble with the camp leader for staying up all night chatting. It gets a bit out of hand when the two belt out a duet of Alanis Morissette’s song “Ironic.” They go to bed, finally, but not before Timberlake says, “Best friends forever?” and Fallon answers, “Best friends forever.”
Lady Gaga
No one knows what to expect when Gaga sits down for an interview. This time she was dressed in a batgirl getup. The costume included studded knee-high boots and a bat mask. A black leather jacket covered a leather bikini.
She was there to announce "Born this Way." “Pick it up in stores,” the media-savvy diva said. Talking about the NYC underground music scene where she used to do a variety show in a bikini, she instructed, “If you take your clothes off, it’s amazing what will happen.” Letterman didn’t bat an eye. He was in his element, enjoying her performance.
Shirley MacLaine
David Letterman did not enjoy a visit by legendary performer Shirley MacLaine, and, by the end of the interview, neither did the Oscar-winning actress. She was there for a new movie called "Madame Sousatzka."
At first, the host who was previously, in 1986, called the A-word by Cher, was hamming it up. He quizzed MacLaine relentlessly about her theories and beliefs in past lives. She didn’t want to talk about it. Finally, she blurted out that Cher was right to call him the A-word. It went downhill from there. He ended it with the standard catchphrase that they were out of time.
Jay Leno & Jimmy Kimmel
Jay Leno did not start the long-lasting feud between the two late-night show hosts, but he shifted it into high gear when he declared that Jimmy Kimmel has a mean streak and that’s the reason he’s in third place in the ratings. Ouch!
The feud was lit with a Leno impression. Jimmy Kimmel mocked Leno relentlessly for an entire episode of " The Jimmy Kimmel Show." Leno told the "Today" show that he never had any problems with Kimmel. In 2017, the feud ended. Kimmel’s newborn needed open-heart surgery, and Leno called to wish him the best. We guess all's well that ends well.
Tracy Morgan
When "SNL" stand-up comedian Tracy Morgan sat down next to Conan, he was starring in "The Last OG." Five years earlier on the show, he was outrageous as usual. Morgan called the president a gang banger and said he should get a teardrop tattoo.
Since then, both of these individuals have been through some serious changes. Conan's show ended up coming to an end, and now he has a podcast. While Morgan suffered a serious accident back in 2014 that he has since recovered from. We're just relieved that these two hilarious individuals are still alive and kicking and doing their thing.
Jim Carrey
Jim Carrey’s visit to "The Tonight Show" in 1994 was epic. At his " Dumb and Dumber" best, Carrey sat down with Jay Leno and announced immediately that he had hypnotized the entire studio audience. He mind-controlled everyone to applaud wildly at his word. As proof, he says that is how he got three number-one hit movies in a row.
It gets a bit weird when he tells his alien abduction story and proves it by pulling up his shirt and drawing a sharpie line in a dot-to-dot map of his moles, but it’s Jim Carrey. This guy knows how to be weird.
Shaquille O’Neal
Jimmy Fallon puts on Shaq’s suit coat in this interview. The host looks as if his head shrunk, swimming in the jacket that goes past his knees. Meanwhile, Shaq attempts to wear Fallon’s coat, and he can’t even get his arm into the sleeve.
It turns out the former Laker star is promoting a new suit line at Macy’s. When Fallon asks if he has ever rejected a promotional gig, Shaq says he turned away a fragrance line called DNA cologne because they wanted samples of his bodily fluids to make it. This interview was just good old-fashioned comedic gold!
Kanye West
Anytime Kanye West makes an appearance; we buckle up. He never lets us down. Kanye joined Kimmel on "Jimmy Kimmel Live" following a heated Twitter fight between the two. Kimmel asked trigger-friendly questions leading Kanye to say he enjoys it when people are mad at him.
Kimmel burst out laughing when the celeb asked if he could imagine him telling his publicist that he is going on TV again. But then the rapper-turned-entrepreneur dove deep, getting into why people are all actors on a stage called life and that the only way out is to “break the simulation.” Whoa, dude.
Benedict Cumberbatch
This really happened. Jimmy Fallon had Benedict Cumberbatch on the show for a Mad Libs game. Cumberbatch chose various nouns, verbs, and adjectives to fill in the blanks as Fallon writes them down. Then, like at a kids' sleepover game, they act out the scene.
If you are a big Cumberbatch fan, it might be difficult to sit through the act. The awkward skit drags on. At last, the iconic "Doctor Strange" actor breaks into a verse of “Baa Baa Black Sheep.” At this point, fortunately, it ends. Cumberbatch should just stick to serious acting stuff if we're going to be perfectly honest.
Brad Pitt
Brad Pitt received an unexpected gift when he visited Conan O’Brien to promote " Troy" (2004). O’Brien gave the A-lister his emerald-green 1992 Ford Taurus SHO. The manual transmission sedan had made many appearances on the late-night talk show as Conan’s first car from college.
In this interview, we got to see Pitt rev and rip out of a parking spot with a quick slip of the clutch. O’Brien warned him not to go over 35 mph because he said the bottom might drop out. He comments that Brad and Jennifer are going to be very happy in that car.
Will Ferrell
Not to be outdone, Will Ferrell advances Letterman’s creep factor one-up on Conan. Dressed in a full Ron Burgundy costume, Ferrell arrives on stage playing the flute. He says he is there to make a big announcement. His big news is that there will be a sequel to "Anchorman: The Legend of Ron Burgundy.” The audience was thrilled.
However, even Conan was grossed out by Ferrell’s own clarification of what he meant by a crude innuendo. It can’t be printed here, but if you want to witness the cringeworthy moment, watch the segment! We're sure you can find it somewhere on YouTube!
Tom Hanks
This late-show gag proves Tom Hanks is really as much of a good sport as we think he is. After promoting so many amazing movies, You'd think that Hanks knows how to do a straightforward interview on a chat show. The iconic actor appeared on Conan O’Brien’s new TBS show in 2010.
One of Hanks's most memorable films is "Splash," and this segment included a big splash. From Conan’s desk, the two were observing a pod of humpbacks. Gazing at the Jumbotron, Hanks clearly adores whale life. He proves his whale knowledge by explaining that a breach requires 40 percent of the creature to break the surface. Just then, splash! Conan, however, remains dry.
Jennifer Garner
This happened a while ago. In 2003, Jennifer Garner came on "Late Night" with Conan to talk about "Daredevil ." The host, clearly impressed with the actress’s work in the film and the martial arts techniques she uses, is sidelined when Garner tells him he misused a word. She points out that "snuck" isn’t a word, and Conan went to Harvard, so he should know that.
Conan, dejected, facetiously admits he went to Harvard driving school. He didn’t let it go. Later in the interview, Conan pulls out a dictionary and points to the word “snuck,” laughing maniacally like an evil supervillain. Yikes.
Bill Maher
Stephen Colbert welcomed late-night host Bill Maher to the show during the 2016 presidential elections. It started out okay, but Colbert asked Maher a specific question one too many times. Maher screamed at Colber to stop asking that, totally creeped out. Colbert wouldn’t stop. At one point, the "Real-Time" host threatened to abandon his seat after the break.
Later, sarcastic sweet nothings like “baby doll” by Maher and “sweetheart” by Colbert dot the conversation as they try to get along for the rest of the segment. It ends with Colbert demanding a better guest. This is what happens sometimes when one host interviews another one.
Norman Mailer & Gore Vidal
Dick Cavett couldn’t help noticing Norman Mailer and Gore Vidal were engaged in a tit-for-tat feud played out in print media. So, he invited two towering intellectuals to face each other on his show in 1971.
It was vicious. At one point, Mailer accused Vidal and the rest of the panel of being intellectually inferior to himself. It was then that Cavett suggested that Vidal might like two other chairs to contain his giant intellect. By the end, the entire audience vociferously turned against Mailer. Cavett made some enemies during his tenure, but that's expected for any late-night chat show host.
Arnold Schwarzenegger
Bill Clinton surprised everyone as the first sitting president to make a late show appearance. By 2003, Arnold Schwarzenegger would take politics and celebrity to a new level when he went on "The Tonight Show" with Jay Leno to announce his run for governor of California.
He told Leno that he supports the recall of the current governor, and then he announced his plan to unseat him. As would be expected, yet shocking at the time, Schwarzenegger went full Terminator on the California governor. Let's face it, has there ever been a late-night chat show interview involving "The Governator" that wasn't hilarious?
Jeff Goldblum
Jeff Goldblum, talking to Cavett in 1992, had starred in “Invasion of the Body Snatchers,” “The Big Chill,” and “The Fly,” long before he would lead the "Jurassic Park" franchise. It's safe to say that he was already a huge name, and things were only going to get bigger for him after this interview.
Goldblum was caught off guard in this interview when Cavett informed him that writers often describe him as “gangly.” Cavett attempted to soften the question by describing the time a man ridiculed him for his short stature, but the conversation was slow to start after that “gangly” remark.
Taylor Swift
Taylor Swift’s dating history is almost as newsworthy as her music career. Like most of us, however, she would rather not talk about her famous exes. Unfortunately, Ellen DeGeneres didn’t give her a choice. And it's kind of unavoidable, as Taylor Swift's celebrity dating history is kind of incredible.
During their interview, Ellen projected images of Taylor’s exes on a massive screen, basically implying that she had dated many men. Though a visibly-uncomfortable Taylor told the host that she doesn’t know if she's going to rehash her past relationships, Ellen said, “Yeah, you will.” Ellen got her way eventually. Talk about awkward!
Madonna
It takes two to tango, and in this case, it took two celebrities to make television viewers deeply uncomfortable. When Madonna stopped by the David Letterman show in 1994, things quickly got weird. First, David began pressuring her to kiss a random person in the audience, refusing to take no for an answer.
Then, Madonna made everyone cringe when she revealed she had given David a pair of her undergarments, telling him to show the audience. The interview was so uncomfortable and inappropriate we couldn’t turn it off fast enough! Let's be fair, put these two in a room together and things are always going to get awkward.
Mariah Carey
While it’s quite common for talk show hosts to tease answers out of their celebrity guests, it’s often done in a tasteful and humorous way. Sadly, that wasn’t the case when singer Mariah Carey visited the Ellen DeGeneres show in 2008. She was about to be forced to reveal some pretty private news!
The host demanded that Mariah address the rumors of her pregnancy, even pressuring her to drink an alcoholic beverage to prove that she wasn’t pregnant! Naturally, the mom-to-be was forced to admit her very private news, later calling the event “extremely uncomfortable.” Not cool at all, Ellen!
Paris Hilton
There are some moments that most people would prefer to forget. Moments like going to jail, for example. Unfortunately for celebrity Paris Hilton, David Letterman wasn’t going to let her off that easily. Though their interview began pretty casually (talking about different cities), David began asking the socialite about her 2007 stint in jail.
A visibly uncomfortable Paris initially answered David’s relentless questioning before telling him she would prefer not to talk about it since she’s moved on — a hint she hoped the host would take. We can't keep up with how many times this kind of thing has happened on Letterman's show over the years.
John Cleese
John Cleese has a problem with the prop table sitting between the two men. It’s wobbly and cheap and not properly standing; it’s got two legs on the hard floor and one on the rug. It wobbles each time they lift their mug for a drink.
With a sudden swoop of dramatic flair, Cleese, the actor, comedian, and producer, best known for “Monty Python and the Holy Grail” (1975), throws the table off the set, but not before dousing the camera lens with the water left in his mug. Problem solved. Now, can we get back to the conversation about forgetting things?
Jennifer Lopez
Jennifer Lopez is known for her sensual and trend-setting style, but even the most self-confident person has boundaries. During a particularly uncomfortable interview with David Letterman, JLo was treated like an object when his camera crew zoomed in on her chest. Jenny From the Block was obviously not happy about this at all.
To make matters more inappropriate, the host referred to her bosom as “pretty darn good.” Jennifer looked clearly uncomfortable as she tried to cross her arms and block the camera’s (and the host’s) view. The whole segment just made us feel gross! We can’t imagine how the star must have felt!
Sofía Vergara
It is no surprise that comedian Ellen DeGeneres has many people divided. According to many, her 2017 interview with “Modern Family” actress Sofía Vergara was just one of many times the host has shown her true colors. In the interview, Ellen poked fun at Sofía’s accent and English language skills as she attempted to teach the “America’s Got Talent” judge new words in English.
Viewers watched as Sofía awkwardly agreed and said, “Okay, I know English.” Ellen chose very challenging words like “flabbergasted” and “discombobulated.” While Sofía says she was in on the joke, many felt it was insensitive. Come on, Ellen!
Mark Wahlberg
As one of the most beloved talk show hosts in the UK, Graham Norton has interviewed multiple celebrities. No part of that experience, however, could have prepared him for an inebriated Mark Wahlberg as a guest. This guy knows how to push the buttons of the people interviewing him!
The boozed-up actor not only kept interrupting fellow guests but, at one point, he actually sat on Graham’s lap and groped him! The host called the whole incident “annoying” but understood that his behavior was due to jet lag and having too many adult beverages. Hmmm… Somebody get Marky Mark a cup of tea and a pillow!
Tyler Perry
Who hasn't used a lame excuse to get out of going somewhere they did not want to go? While our little white lies would not get called out on national television, the same can not be said about Jimmy Kimmel and Tyler Perry. It turns out that the director invited Jimmy to his big party — an event Jimmy apparently promised to attend but didn’t.
Viewers watched as the host tried miserably to come up with excuses as to why he was a no-show — excuses that were promptly called out by the party-throwing “Madea” star. Should’ve just RSVP’d “no,” Jimmy!
Lindsay Lohan
Though many celebrity interviews may seem unplanned or even unfiltered, most interviews are told to stick to publicist-approved questions or topics when questioning their subjects. David Letterman apparently did not get the memo, especially when Lindsay Lohan arrived on his show one evening.
When interviewing the "Mean Girls" star, the famed late-night talk show host began bombarding her with questions related to her past struggles with substance abuse and her repeated trips to rehab. Lindsay had to awkwardly sit and try to handle the intense questions before telling the host that they didn’t discuss that in the pre-interview. So uncomfortable, folks!
Justin Bieber
Though they may live in the public eye, celebrities still deserve privacy. In 2015, paparazzi caught singer Justin Bieber in his birthday suit while vacationing in Bora Bora. The star thought those embarrassing pictures were a thing of the past. That was until he showed up on a specific celebrity talk show and was given quite a rude awakening.
Unfortunately, while on “The Ellen DeGeneres Show,” the host felt the need to not only talk about the paparazzi shot in Bora Bora, but she also projected the embarrassing images on a huge screen to her audience and millions of viewers. Deeply inappropriate! Justin looked visibly uncomfortable and unable to explain himself.
Mary-Kate and Ashley Olsen
From movies to their own fashion lines, Mary-Kate and Ashley Olsen seemed to be everywhere. But by the early 2000s, the twins were making headlines because of their figures — something Oprah felt the need to touch on during her famous sit-down with them.
Viewers could see that they did not want to discuss their weight, yet Oprah kept bringing it up. At one point, she even asked them, “what size are you, by the way?” — a question many felt was insensitive considering that the twins were already struggling with the media attention. What a shame. Not cool, Oprah.
Robert Pattinson
Remember "The Tyra Banks Show?" The inventor of "smize" decided to add a daytime talk show host to her resume with her very own talk show. In typical Tyra fashion, things got a bit weird, especially when she invited "Twilight" star Robert Pattinson. Yeah, things got out of control, as you can see!
Speaking in a ridiculous British accent, she demanded that Robert bite her neck (like his vampire character does in the films). Feeling too awkward to say no, Robert leaned forward and bit the host in a scene that even the most diehard Twihards (superfans) cringed while watching.
Jennifer Aniston
Having been an actress for decades, it is safe to say that Jennifer Aniston has gone through her fair share of interviews. That said, we do not think anything could have prepared her for this truly confusing interview with Mr. David Letterman.
At some point during the interview, things got a bit hairy between the “Friends” star and the host when he decided to get up close and personal with Jennifer. After breathing into her neck, he then put a lock of hair in his mouth! We really do not know how she sat through the rest of that interview!
Dakota Johnson
It is an unfortunate truth that talk show hosts will say anything to add interest to a conversation with a famous guest, even if it means resorting to lying. In an interview with Dakota Johnson, host Ellen DeGeneres tried to accuse the “50 Shades of Grey” star of not inviting her to a party.
Dakota was not having it. She snapped and corrected Ellen, saying in front of everyone that Ellen actually was invited, despite the host's accusations. After Ellen tried to play dumb, Dakota even told her to ask her producer who could verify! Why would you lie about something like that? Maybe the party sucked, but that's beside the point!
Sophia Loren
“What does Cary Grant have that I don’t?” After an extremely awkward laugh to fill the silence, Sophia Loren bats her eyelashes and offers a litany of compliments. She said the host has charm; he has elegance, he has grace, he talks beautifully, and he has a nice mind. The point is, really, Cavett failed to get the actress to speak about her affair with Hollywood legend Cary Grant.
In return, Loren fights back and pressures the host about what makes a woman attractive. Cavett veers down several tangents to ditch the question, but she persists. He finally says it is an unknowable thing. Awks!
Celine Dion
With such a legendary career, we are not sure how Ellen DeGeneres’s interview with music icon Celine Dion reached the point where they were talking about the length of Celine’s son’s hair. How random can you actually get?
Apparently, the singer had a problem with comments about his long hair, especially after Ellen asked when Celine and her husband were going to cut their son's hair. The singer then asked if the host had a problem with it before Ellen changed the subject and ended that very weird exchange. As a host, she should know that children are a touchy subject for most parents!
Naomi Cambell
Some celebrities feel that if they air their dirty laundry, it will help them find closure. Perhaps that is what former model Tyra Banks thought would happen when she brought rival supermodel Naomi Cambell onto her talk show in 2005.
Unfortunately, Naomi basically denied any wrongdoing or said she could not remember any of the events and, at one point, implied Tyra was lying about Naomi trying to sabotage her modeling career. As predicted, the disastrous interview did not bring the two fashion icons any closer, and the two are still feuding until this very day! Some things never change.
BTS
When interviewing someone from another country or culture, it is important to understand the cultural differences regarding different topics such as dating and relationships — something talk show host Ellen DeGeneres learned the hard way when a certain Korean supergroup showed up.
During an interview, the host decided to ask pop group BTS if they had ever “gotten together” or “hooked up” with their fans. When she was met with silence, she asked the band’s translator to translate her way-too-personal question, making the seemingly-conservative translator and the boy band members deeply uncomfortable. To be honest, this would be awkward in any language.
Britney Spears
There are some ideas that television writers come up with that, in reality, should never see the light of day, and this was one of them. For some reason, late-night host David Letterman decided to have pop star Britney Spears present a list called “Top Ten Ways the World Would Be Different if Britney Spears Were President” … all while wearing just a bikini.
Considering the star’s struggles with mental health and substance abuse, the whole segment just felt exploitative and uncomfortable, not to mention David poking fun at her intelligence. Just mean! To be fair, Britney hasn't been seen doing anything quite like this in a long time.
Hugh Hefner
Sweet-talking women was Hugh Hefner’s forte, so when he faced two activists Susan Brownmiller and Sally Kempton on “The Dick Cavett Show,” he went for this approach. We would expect nothing less from the Playboy legend.
Brownmiller makes confrontational remarks right off the bat, calling Hefner her enemy. But still, he tries to soften the discussion by saying he is sympathetic to “girls.” The women immediately check him and ask if he should be called a boy or, perhaps, wear a white puffy tail on his rear end. Such a savage moment in the world of cringeworthy talk show incidents.
Draya Michele
Some viewers turn to the Wendy Williams show because they appreciate Williams’s in-your-face personality and candid style of interacting with her guests. Known as a “shock jockette” for her bold interview style, she usually knows how to get the scoop. Unfortunately, that can often mean crossing the line. Take this situation, for example.
When interviewing “Basketball Wives” reality star Draya Michele, the host asked Draya how many basketball players she had been with, before justifying her question by adding that Draya has gotten around. To say we were stunned would be an understatement! And obviously, Draya was absolutely stunned too!
Lily Tomlin
Lily Tomlin and Chad Everett join Cavett to talk showbiz. A perfectly normal situation. Actor Everett goes on about choosing his stage name. Cavett interrupts to plug comedian Tomlin’s new album, probably because Everett is dominating the conversation by talking about himself.
His rambling took a negative direction. He announced that he had three horses, three dogs, and a wife. The host gives him a chance to correct himself. But he drove it home, saying that his wife is the most beautiful animal I own. Lily Tomlin, no longer able to tolerate the egomaniac, walks off. And after an illustrious career, she has never looked back.