Late-night talk shows have been a staple of television for decades, providing a platform for celebrities, politicians, and other public figures to promote their work, share their opinions, and entertain audiences. However, over the years, there have been moments when things didn't quite go as planned, leading to some of the most cringe-worthy and memorable moments in late-night talk show history.
Madonna
On her first appearance on "The Tonight Show" with Johnny Carson in 1987, Madonna was at the peak of her career and her performance was highly anticipated.
The interview ended on a sour note, with Carson telling Madonna, "You're a nice lady," and Madonna replying, "And you're not so bad yourself." The moment became one of the most cringe-worthy and iconic in late-night talk show history.
Jennifer Aniston
One particular dress that Aniston wore on the show garnered a lot of attention and controversy.
During a 1998 appearance on the show, Aniston wore a very revealing black dress that showed off a lot of cleavage. The dress was seen as provocative by some viewers, who criticized Aniston for wearing it on national television. During the interview, Letterman asked Aniston about the dress, jokingly asking her if she had "dressed up" for him. Aniston laughed off the comment and defended her choice of clothing, saying that she felt comfortable and confident in the dress and that she didn't think there was anything wrong with it.
Raquel Welch
Raquel Welch and Dick Cavett had an interview on "The Dick Cavett Show" in 1971.
Welch was promoting her latest film at the time, and during the interview, she expressed her displeasure with some of the questions Cavett was asking her, particularly about her love life. The interview has been replayed numerous times and has become a classic example of a celebrity interview gone awry.
Halle Berry
Halle Berry appeared on The Tonight Show with Jay Leno in 1998 to promote her movie "Bulworth."
She discussed her experiences filming the movie, working with co-star Warren Beatty, and her personal life. She also talked about the challenges she faced as a black actress in Hollywood and the importance of representing diversity in the entertainment industry.
Janis Joplin
Janis Joplin appeared on "The Dick Cavett Show" in 1969, where she gave a candid interview and performed two of her hit songs, "Half Moon" and "My Baby".
During the interview, Joplin discussed her musical influences, her struggles with drug addiction, and the societal pressures she faced as a woman in the music industry. The interview is considered a classic moment in television history, showcasing Joplin's raw talent and personal charisma.
Anna Nicole Smith
One notable appearance was in 1994, where she famously flirted with Leno and showed off her famous curves in a revealing outfit.
In 1996, she returned to the show to promote her reality TV series "The Anna Nicole Show" and discuss her personal life, including her marriage to billionaire J. Howard Marshall. She made several more appearances on the show in the years leading up to her tragic death in 2007.
Adrienne Barbeau
Adrienne Barbeau's appearance on "The Tonight Show" with Johnny Carson in 1978 quickly took an uncomfortable turn.
Carson began the interview by complimenting Barbeau on her appearance and then proceeded to make several comments about her body, including asking her about her "measurements." Barbeau seemed uncomfortable with the line of questioning, but Carson persisted, making inappropriate jokes and comments throughout the interview.
Donna Summer
Perhaps most remembered for the awkward exchange between her and Johnny Carson.
Carson introduced Summer as the "Queen of Disco" and asked her about a rumor that she did not wear underwear. Summer looked visibly uncomfortable and responded with a brief denial. Carson continued to press the issue, making several more comments and jokes about it, despite Summer's obvious discomfort.
Sarah Shahi
Sarah Shahi on "The Late Late Show with Craig Ferguson" in 2011.
She shared stories about her time as an NFL cheerleader and talked about her love for motorcycles. Shahi also showed off some of her dance moves and even convinced Ferguson to join her in a salsa dance.
Zsa Zsa Gabor
One particularly memorable appearance was in 1968, where she talked about her famous catchphrase "dahling" and shared stories about her many marriages and love life.
At one point in the interview, Gabor even flirtatiously grabbed Carson's hand and asked him to marry her. The exchange was playful and humorous, and became a classic moment in the show's history.
Carrie Keagan
In 2011 when she wore a tight-fitting, low-cut yellow dress that caught Ferguson's attention.
The two bantered back and forth about the dress, with Keagan teasing Ferguson for staring at her chest. The segment has since become somewhat infamous and has been viewed millions of times online.
Doris Day
Doris Day made several appearances on "The Tonight Show Starring Johnny Carson" throughout her career, including in 1976, 1985, and 1987.
She discussed her acting and singing career, as well as her personal life. During her 1976 appearance, she sang a song and joked with Johnny Carson about her fear of flying. In her later appearances, she talked about her animal activism and the Doris Day Animal Foundation.
Sydney Sweeney
SNL continues to be criticized for cringeworthy writing.
Sydney Sweeney is the latest host leaving viewers wondering why the show just resorts to jokes about being attractive when it has a "hot" guest.
Cassandra Peterson
Cassandra Peterson, who played the character of Elvira, Mistress of the Dark, appeared on "The Tonight Show" with Joan Rivers on Halloween night in 1985.
The two discussed Peterson's character and the upcoming release of her first film, "Elvira, Mistress of the Dark." The segment included a comedy skit with Elvira and Rivers, as well as an interview in which Peterson discussed her career and her experience as a horror host.
Ann-Margret
She made several appearances on "The Tonight Show Starring Johnny Carson" throughout her career, showcasing her talent as a singer and actress.
One of her most memorable appearances on the show was in 1973, where she surprised Johnny Carson by singing "Bye Bye Birdie" in a sexy and playful performance. The audience went wild, and Carson himself was clearly enjoying the show.
Carol Wayne
Carol Wayne was an American actress and a regular performer on "The Tonight Show Starring Johnny Carson" from the mid-1960s through the late 1970s.
She was known for her comedic roles, as well as her statuesque beauty and distinctive voice. Wayne was also a frequent guest star on various television shows, including "The Love Boat," "The Fall Guy," and "Fantasy Island." Unfortunately, Wayne passed away in 1985 at the age of 42.
Whitney Houston
Whitney Houston made an appearance on "The Tonight Show with Jay Leno" in 1990 to promote her album "I'm Your Baby Tonight".
During the interview, she discussed her upbringing, her music career, and her recent performance at the Super Bowl. She also performed a rendition of "I'm Your Baby Tonight" for the studio audience. The interview was well-received and helped to further cement Houston's status as a pop icon.
Yvonne Craig
Yvonne Craig was an American actress, best known for her role as Batgirl in the 1960s television series "Batman."
One of Yvonne Craig's appearances was on "The Merv Griffin Show," a popular talk show that aired from 1962 to 1986. Craig appeared on the show multiple times throughout the 1960s and early 1970s, discussing her career in Hollywood and promoting her various projects.
Mirandra Kerr
Miranda Kerr, the Australian model and businesswoman, has made several appearances on late-night talk shows, including "Conan."
And here is when the camera caught Conan O’Brien staring at Miranda Kerr. Men will be men.
Charo
Charo, also known as María del Rosario Pilar Martínez Molina Baeza.
Spanish-American actress, comedian, and flamenco guitarist who became famous in the 1970s for her lively personality and catchphrase "cuchi-cuchi." Charo's vibrant personality and talent as a flamenco guitarist made her a beloved guest on late-night talk shows, and her appearances remain a cherished part of television history.
Loni Anderson
She rose to fame in the 1970s and 1980s, starring in popular sitcoms such as "WKRP in Cincinnati" and "Three's Company."
Her most memorable appearances on the show was in 1981, when she discussed her role in the film "The Jayne Mansfield Story," in which she portrayed the iconic actress. Anderson talked about the challenges of portraying Mansfield and the research she did to prepare for the role.
Nicole Kidman
In 2015, Kidman's performance on The Tonight Show Starring Jimmy Fallon was one of her most memorable appearances.
She revealed that she had a crush on Fallon when they both were single and that he missed an opportunity to date her. Fallon was shocked and surprised, as he had no idea that Kidman was interested in him at the time.
Rebecca LaRue
Rebecca LaRue was a fictional character that was mentioned in a sketch called "Delicious Dish" that aired on the show in 1996.
In the sketch, Molly Shannon and Ana Gasteyer played the hosts of a public radio show about food called "The Delicious Dish." They interviewed Alec Baldwin, who played a baker promoting his holiday treats, including a dessert called "Schweddy Balls."
Goldie Hawn
One of her most memorable appearances on the show was in 1978, when she spoke about her experience working on the film "Foul Play" with co-star Chevy Chase.
Hawn discussed her approach to comedy and shared some of her favorite moments from filming the movie. She also talked about her personal life, including her relationship with actor Kurt Russell, whom she had met on the set of the film.
Sofia Vergara
Sofia Vergara gave Colbert a pair of her underwear as a gift.
The exchange came about when Colbert asked Vergara about her lingerie line, and she responded by saying that she had brought him a present. She then pulled a lacy pair of underwear out of her handbag and handed them to him.
Farrah Fawcett
Farrah Fawcett known for her iconic role as Jill Munroe in the 1970s television series "Charlie's Angels."
Fawcett's appearance on "The Tonight Show" was widely praised for its honesty and bravery, and helped to raise awareness about cancer and the importance of early detection and treatment. Fawcett passed away in 2009 at the age of 62, but her legacy as a talented actress and advocate for cancer awareness continues to this day.
Nina Dobrev
Nina Dobrev uses Conan as her human yoga wall.
Nina Dobrev showed off her impressive yoga skills by using host Conan O'Brien as her "human yoga wall." Dobrev, known for her role in the TV series The Vampire Diaries, demonstrated various yoga poses on the show.
Dolly Parton
One of her most memorable appearances on the show was in 1977, when she performed her hit song "Here You Come Again."
Dolly Parton has remained a beloved figure in popular culture, and her appearances on "The Tonight Show" helped to showcase her talent as a performer and her warmth and humor as an interviewee. She has continued to release new music and remain active in various charitable causes, solidifying her status as an American icon.
Shakira
Shakira steals the show in an unforgettable see-through dress.
In May 2022, she appeared on The Tonight Show Starring Jimmy Fallon. Shakira knows how to create a stir among her fans regardless of whether she is performing her latest single or trying out TikTok dance trends.
Joey Heatherton
Joey Heatherton is an actress, singer, and dancer who rose to fame in the 1960s and 1970s.
Heatherton first appeared on The Ed Sullivan Show in the 1960s, where she quickly became a popular guest due to her singing and dancing abilities. She later appeared on other late-night talk shows such as The Mike Douglas Show, The Merv Griffin Show, and The Tonight Show Starring Johnny Carson.
Drew Barrymore
The most famous moments from Barrymore's appearances on the Late Show with David Letterman occurred in 1995.
She famously flashed her breasts to the host during an interview. At the time, Barrymore was just 20 years old and was promoting her film "Bad Girls." The incident made headlines and has become one of the most infamous moments in the show's history.
Jennifer Lawrence
A dirty nose left Jennifer Lawrence red-faced on Jimmy Fallon.
During an appearance on the show in 2015, Lawrence was playing a game of "Box of Lies" with Fallon. As she was describing the contents of the box, she suddenly paused and looked embarrassed. Fallon quickly realized what was happening and handed her a tissue.
Natalie Morales
One particularly appearance was in May 2019 when she discussed the challenges of covering the news in the age of Trump and the importance of journalists being objective and accurate.
She also discussed her new show "Abby's," which she starred in and produced. Additionally, Morales and Meyers participated in a game where they had to guess which headlines were real news stories and which were fake.
Elizabeth Banks
In 2005, she promoted the film "The 40-Year-Old Virgin" in which she had a supporting role.
During the interview, she and Conan discussed her character's obsession with shoes, and she even brought out a pair of high-heeled boots to demonstrate. The segment was playful and lighthearted, and demonstrated Banks' comedic timing and charm.
Gordon Ramsey
Chef Gordon Ramsay and actress Sofia Vergara made a joint appearance on "The Tonight Show with Jay Leno" in August 2010 to promote their new show "MasterChef."
The interview has been dubbed "uncomfortable," with many accusing Ramsay, in particular, of acting inappropriately toward Vergara.
Pamela Anderson
Pamela Anderson has appeared on The Tonight Show with Jay Leno multiple times throughout her career, dating back to the 1990s.
Anderson, who is known for her role on the TV series "Baywatch," came out in a tight, low-cut dress and boots that drew cheers and whistles from the audience.
Nicole Kidman, Again
'Kidnapped' Jimmy Kimmel gets a sexually provocative lap dance from Nicole Kidman.
On national television, Nicole Kidman gave Jimmy Kimmel a lewd, sexually provocative lap dance.
Kim Kardashian
Jennifer Lawrence confused Kim Kardashian's makeup product for a sex toy.
Kardashian admitted that she was unaware that so many of her products are "flesh colored," but said she was used to toys with a "darker color."
Robert Pattinson
Pattinson jokingly bites Tyra Banks on the neck during an interview in 2008.
The clip has been shared widely on social media and has been referenced in various memes and jokes over the years. Despite the playful nature of the moment, it sparked some controversy at the time, with some critics arguing that Pattinson's behavior was inappropriate and that it perpetuated dangerous stereotypes about vampire and sexualized behavior.
Andy Dick
In 2016, Ivanka Trump appeared on Jimmy Kimmel Live! alongside Andy Dick.
He inappropriately touched Trump throughout the interview, forcing security to carry him off the stage while cameras continued to roll.
Larry King/Marlon Brando
Marlon Brando appeared on "Larry King Live" in 1994 and gave the talk show host a surprise kiss on the lips.
Brando was discussing his new film, "Don Juan DeMarco," and suddenly leaned over to give King a peck on the lips. King was visibly surprised and taken aback by the unexpected gesture, but took it in stride and continued with the interview.
Salma Hayek
Salma Hayek appeared on The Tonight Show with Jay Leno in 1999 to promote her movie "Dogma".
She talked about her role in the movie and pokes fun at Leno with her minxy accent and broken English.
Susan Anton
She was a frequent guest on various talk shows during the 1970s and 1980s, including "The Tonight Show" and "The Merv Griffin Show."
One memorable moment on "The Merv Griffin Show" involving Susan Anton occurred in 1979. Anton was singing a song called "Killin' Time" while wearing a revealing dress that had a long slit up the side. During the performance, her dress slit opened a little too far, revealing her underwear to the audience.
Chris Pratt
Pratt appeared on The Graham Norton Show in 2016, while promoting the film "Passengers."
During the episode, he discussed working with co-star Jennifer Lawrence and the challenges of filming a sci-fi movie. He also talked about his personal life, including his marriage to actress Anna Faris and their young son.
Justin Bieber
Letterman scolds Justin Bieber for his new tattoo.
Bieber defended his tattoo, saying that it represented his faith, but Letterman continued to tease him about it. "Is that a Canadian thing? I mean, what does that mean?" Letterman asked. The exchange between Letterman and Bieber became somewhat tense, with Bieber appearing to become frustrated with the line of questioning.
Selena Gomez
Selena Gomez appeared on The Tonight Show Starring Jimmy Fallon in January 2020 wearing a black and white floral mini dress by Miu Miu, paired with black tights and black pumps.
She completed her look with her hair styled in loose waves and minimal makeup. During her appearance, she played a game of "Can You Feel It?" with Jimmy Fallon, where they had to guess what objects they were touching while blindfolded.
Fran Drescher
Fran Drescher in a black crop-top and skirt on The Tonight Show with Jay Leno in March 1996.
In March 1996, Fran Drescher appeared on The Tonight Show with Jay Leno to promote her TV show "The Nanny." She was wearing a black crop-top and a black skirt for her appearance on the show. During the interview, she talked about her experience working on "The Nanny" and her personal life.
Margot Robbie
Margot Robbie appeared on The Tonight Show Starring Jimmy Fallon in February 2020 to promote her film "Birds of Prey."
She wore a beautiful Oscar de la Renta dress in a vibrant shade of pink. The dress featured a fitted bodice with spaghetti straps and a flowing, full skirt that fell to her ankles. She paired the dress with simple black heels and wore her blonde hair styled in loose waves.
Beyoncé
Beyoncé appeared on "The Tonight Show with Jay Leno" in February 2007 to promote her album "B'Day."
She performed her hit single "Irreplaceable" and also talked about her experience performing at the Super Bowl halftime show earlier that month.
Jessica Simpson
On September 7, 2006, Jessica Simpson appeared on The Tonight Show with Jay Leno.
Simpson discussed her upcoming movie "Employee of the Month," her newly released album "A Public Affair," and her personal life, including her divorce from Nick Lachey.
Diane Lane
Diane Lane is an American actress known for her work in film, television, and on stage.
She has appeared in numerous critically acclaimed movies, including "Unfaithful," "The Outsiders," "Under the Tuscan Sun," and "Man of Steel." Diane Lane has made several appearances on various talk shows throughout her career, including "The Tonight Show Starring Johnny Carson" and its successor, "The Tonight Show with Jay Leno."
Sonny & Cher
Sonny and Cher first appeared on The Merv Griffin Show in 1965.
One memorable moment from their appearances on The Merv Griffin Show was when Cher announced her pregnancy with their daughter Chastity, who later became known as Chaz Bono.
Jean Shrimpton
Also known as "The Shrimp," was a popular fashion model in the 1960s.
One of the most memorable moments from Shrimpton's appearances on late-night talk shows was when she appeared on The David Frost Show in 1968, and was asked to define what she considered to be the essence of beauty. Shrimpton's thoughtful response became a topic of discussion in the media and helped to cement her reputation as an intelligent and thoughtful person, in addition to her beauty.
Justin Timberlake
The most popular sketch that Justin Timberlake has done on "The Tonight Show Starring Jimmy Fallon" is called "Camp Winnipesaukee."
The sketch features Timberlake and Fallon playing teenage campers at Camp Winnipesaukee, a fictional summer camp. The two hosts dress up in camp t-shirts, shorts, and hats, and speak with exaggerated teenage accents.
Lady Gaga
Lady Gaga has made several appearances on "Late Show with David Letterman" over the years, including one particularly memorable appearance in 2011.
During the interview, Letterman asked Gaga about her unique sense of style and her choice of clothing. He then asked her if she could walk across the stage in her sky-high platform heels without tripping, to which she confidently responded "Yes, I can." Gaga then proceeded to stand up and walk across the stage in her platform heels, but as she walked back towards Letterman's desk, she suddenly stumbled and fell to the ground. Despite the fall, she quickly got back up and joked about the incident, saying "I knew that was going to happen!"
Emma Watson
The British actress best known for playing Hermione Granger in the Harry Potter film series. once confused Jimmy Fallon for Jimmy Kimmel during an appearance on The Tonight Show Starring Jimmy Fallon.
She confused Jimmy Fallon for Jimmy Kimmel during an appearance on The Tonight Show. During the interview, Fallon asked Watson about a recent visit to the set of the Star Wars film franchise. Watson began to recount her experience and mistakenly referred to Jimmy Fallon as "Jimmy Kimmel," prompting Fallon to laugh and correct her.
Jason Momoa
During a 2019 appearance on the show, Momoa participates in a sketch called "Momoa's Dream."
He goes to a convenience store to buy a can of beer but ends up performing a hula dance in the parking lot. While Momoa does take off his shirt in the sketch, he does not strip down completely.
Shaq
Fallon wears Shaq's suit coat in this interview.
It looks as if the host's head has shrunk in the jacket that extends past his knees. Shaq tries to wear Fallon's coat, but he can't even get his arm into the sleeve.
Kimmel/Damon Feud
The Jimmy Kimmel/Matt Damon feud is a long-running inside joke that originated on "Jimmy Kimmel Live!"
The feud began in 2006, when Kimmel jokingly apologized to Matt Damon at the end of an episode for running out of time and not being able to interview him as scheduled. The feud escalated over time, with Kimmel frequently joking about Damon, and Damon appearing on the show to retaliate. Damon once famously hijacked an entire episode of "Jimmy Kimmel Live!" and renamed it "Jimmy Kimmel Sucks!", bringing in a host of celebrity guests to participate in the joke.
Arnold Schwarzenegger
Schwarzenegger announces his candidacy for governor.
Arnold Schwarzenegger is just as much a politician as he is a movie star. But the announcement that he was running for governor of California on The Tonight Show with Jay Leno blew people away.
Kate Hudson
Kate Hudson appeared on The Tonight Show with Jay Leno in 2004 to promote her romantic comedy film "Raising Helen."
She wore a black and white striped top with a matching skirt, paired with strappy black heels. Hudson discussed her experience working with co-star Joan Cusack and how they bonded on set.
Kayne West
While apologizing to Taylor Swift, Kanye West breaks down in tears.
Despite being in the headlines often these days, Kanye West stunned audiences when he cried on The Tonight Show with Jay Leno. During Taylor Swift's acceptance speech at the MTV Video Music Awards, West interrupted Swift's speech to praise a Beyoncé video. West was publicly lambasted for his behavior.
Mischa Barton
Mischa Barton appeared on The Tonight Show with Jay Leno in 2005 to promote the TV show "The O.C."
She talked with Jay Leno about her experience on the show, her childhood, and her upcoming projects. During the interview, she also talked about her passion for music and how she hoped to pursue a music career in the future.
Hugh Grant
After getting caught with Divine Brown, Hugh Grant confesses he "did a bad thing."
A few weeks before announcing his first big feature, Nine Months, Hugh Grant found himself in some sticky legal trouble. In a public area, police caught Grant engaging in sexual activity with Estelle Marie Thompson, aka Divine Brown.
David Letterman
In 2009, David Letterman revealed on his late-night talk show, "Late Show with David Letterman," that he had been the victim of an extortion attempt.
Letterman disclosed that he had engaged in sexual relationships with members of his staff, and that someone had threatened to go public with the information unless he paid a large sum of money.
Shari Belafonte
Daughter of legendary singer Harry Belafonte has made a name for herself as a talented and versatile performer in her own right.
Belafonte made several appearances on "The Merv Griffin Show" throughout the 1980s. Her most memorable appearances on the show was in 1986, when she discussed her role on the hit television series "Hotel," which aired from 1983 to 1988.
John Oliver
John Oliver, the host of the HBO show "Last Week Tonight," did a segment on his show in 2016 where he discussed the issue of debt buying.
As part of the segment, he bought and forgave $15 million worth of medical debt. Oliver highlighted the predatory nature of the debt buying industry and the negative impact it can have on people's lives, especially in the case of medical debt.
Craig Ferguson
Craig Ferguson, who is originally from Scotland, took the United States citizenship test on his show "The Late Late Show with Craig Ferguson" in 2008.
He answered questions about American history, government, and culture, while injecting his trademark humor and wit. The segment was well-received and even became a popular clip on YouTube.
Michael Richards
Michael Richards, best known for playing the character of Kramer on the popular TV show "Seinfeld," made racist comments during a stand-up comedy routine at the Laugh Factory in LA.
A few days later, Richards appeared on "Late Show with David Letterman" to attempt an apology for his actions. However, the apology was poorly received, with Richards appearing to become defensive and agitated during the interview.
Rihanna
In December 2012, Rihanna performed her hit single "Diamonds" on the German variety show Wetten, dass.
Rihanna appeared on stage in a white jumpsuit with cutouts at the waist, paired with a diamond choker necklace and sparkling earrings. As she belted out the song, the stage was filled with smoke and dazzling lights, creating a dramatic and memorable performance.
Lady Gaga, Again
Lady Gaga appeared on the Graham Norton Show in November 2013.
She performed her hit single "Do What U Want" with singer R. Kelly. The performance was controversial due to the scandal surrounding R. Kelly at the time.