The Most Memorable & Awkward Segments on Late-Night Talk Shows

From James Corden to Oprah Winfrey, late-night talk shows have continued to be there to entertain us well into the night. The hosts’ humor, mixed with pointed questions, has allowed celebrities to promote and connect with audiences everywhere.

Photo by Ebet Roberts/Redferns

There have been memorable moments, and there have been cringey segments. Hosts may have shifted, but the attraction of late-night shows is everlasting. Let’s take a look at some of the most memorable guests and moments that have appeared on our TV screens over the years.

Madonna

Madonna was the “Queen of Pop” throughout the ’80s. In early June 1987, Madonna made her “The Tonight Show” debut with Johnny Carson. Though many assumed the Material Girl’s appearance would be all other guests on the show, they were sorely mistaken.

Source: YouTube

During the show, Madonna had a plan; she flirted with Carson, flirting to a level that was tough to ignore. Several months after the episode aired, Madonna began her worldwide promotion tour for her “Who’s That Girl” album. Coincidence? We don’t think so.

Raquel Welch

Even if you’re the most accomplished, direct talk show host, you know it’ll be amusing when Raquel Welch is being interviewed. With her beautiful outfits, sparkling smile, and even tan, Welch managed to make the jittery Dick Cavett appear a bit more laid-back.

Photo by Tony Kent/Sygma via Getty Images

The actress’ big break happened with her role in “One Million Years B.C.” Her costume of a deerskin bikini made her an international sensation. She continued working as a singer, model, and actress and is regarded as one of the most stunning stars in film.

Janis Joplin

Janis Joplin is one of the most distinguished artists of all time, and tragically, one of the first members of the 27 Club. A handful of months before her difficult passing, Joplin graced the “The Dick Cavett Show” stage for the final time.

Photo by Michael Ochs Archives/Getty Images

Unfortunately, on August 3rd, 1970, Joplin had her last appearance on the show, singing “My Baby” and “Half Moon.” Notorious for her famed mezzo-soprano voice and dynamic stage presence, the accomplished musician would tragically pass away on October 4th that same year.

Adrienne Barbeau

Several weeks before Christmas 1974, actress Adrienne Barbeau was on “The Tonight Show,” and since it was close to the holiday, Barbeau and Carson began discussing gifts. The young star surprised everyone by revealing that she had welcomed many intriguing presents from lovers throughout the years.

Source: Reddit

These gifts included but were not limited to items to repair a car, encyclopedias, and a fire extinguisher. Being the ever-observant host, Carson noted the “multiple lovers” comment, but Barbeau kept from sharing any additional personal facts.

Donna Summer

Donna Summer came to her “The Tonight Show” interview on November 28th, 1979, with a goal. The “Queen of Disco” ensured that not only was she artistically talented, but she also made sure that Carson and viewers at home were aware of her additional skills.

Photo by Michael Putland/Getty Images

Carson noted that Summer was mechanically skilled, with the ability to repair vehicles, followed by a pretty sexist comment about women not being mechanically inclined. Summer set Carson straight, citing that anything a man can do, a woman is capable of doing as well.

Zsa Zsa Gabor

Thanks to Johnny Carson and Zsa Zsa Gabor, Twister became a staple game. When the “Moulin Rouge” actress was on the show in 1966, the pair used the whole episode to play the game. It came to stores earlier that year, and it was thought that the Milton Bradley game would be hugely popular.

Source: Reddit

Upon its release, it did not blow up as expected. In the months after the interview, Twister sales were through the roof with more than 3 million, primarily due to the two celebrities playing together on TV.

Doris Day

Doris Day, the complex singer and actress, was on “The Tonight Show” back in 1974. Not only did Day take advantage of the show’s platform to share her long list of male co-stars (Clark Gable and James Garner, among them), but she explained her role as an animal rights activist.

Photo by Silver Screen Collection/Getty Images

Advocacy, acting, and singing – the woman seemed to be able to do it all! In addition to her on-screen success in TV and film, Day was also a talented singer. Her most popular songs were “My Dreams Are Getting Better” and “Sentimental Journey.”

Cassandra Peterson

As one of the most commanding guest hosts of “The Tonight Show,” Joan Rivers hosted many recognized guests. During her time on the 1985 Halloween night episode, Rivers interviewed Elvira, the Mistress of the Dark.

Source: IMdb

She was notorious for her exposing clothes, which made Rivers envious of Peterson for most of the night’s episode. The first and debatably most known goth girl, Elvira, was Peterson’s desirable vampire alter ego. Elvira was featured in ’80s movies, TV, and comic books.

Ann Margret

It’s not surprising that actors get stereotyped into parts that they don’t actually enjoy. When it comes to Ann Margret, she was typecast as nothing more than a “B” movie actress. This label was only based on her early movies. On February 29th, 1972, she appeared on Johnny Carson’s couch.

Photo by Sunset Boulevard/Corbis via Getty Images

During their interview, Margret discussed being taken seriously as an actress. She had five Golden Globe awards to her name, along with several other award nominations! She got a chance for redemption with her role in “Carnal Knowledge,” showing a more genuine side of her acting skills.

Susan Anton

There wasn’t a situation that Susan Anton couldn’t brighten, including “The Merv Griffin Show.” When David Brenner interviewed the actress, she stole the segment. Anton was famous for her roles in several Muriel Cigar commercials as well as other radio and print advertisements.

Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

This would be the first of many appearances on “The Merv Griffin Show” for Anton, and though she never booked a prominent breakout role, she was a favorite when it came to choices for guest appearances. She was featured on several successful shows, including The Love Boat” and “Baywatch.”

Carol Wayne

Wayne used her notoriety to become one of the most beloved talk show assistants in TV history. She starred in multiple TV shows and films, though her best-known role was on “The Tonight Show.” She played a scatterbrained Matinee Lady during the Art Fern Tea Time Movie sketches.

Source: YouTube

Over 13 years, Wayne starred in over 100 shows. When the show was shortened to an hour, Wayne’s part lessened, sending her into a spiral. Wayne found herself making poor business decisions, navigating addiction, and getting herself in many financial challenges.

Whitney Houston

One of the iconic voices and names of the 20th century, Whitney Houston, is one of the all-time most successful female artists. She’s sold over 200 million albums globally and is the best-selling female singer to date.

Photo by Ron Galella/Ron Galella Collection via Getty Images

In 1990 Jay Leno had the honor of celebrating the diva for breaking the Beatles’ outstanding record of number one hits. During her iconic interview on “The Tonight Show,” she blew everyone away with her live performance of her hit song, “I’m Your Baby Tonight.”

Yvonne Craig

Substitutable with the superhero, Craig just had to appear in full Batgirl costume on “The Merv Griffin Show” on September 5th, 1967. Refusing to break character, Craig used her interview to endorse women’s rights, emphasizing the importance of equal pay.

Source: Pinterest

In one advertisement, Batman and Robin needed to be saved, but Batgirl wouldn’t release them. This was in protest of the fact that Craig was making less money than Robin. During her career, Yvonne Craig was a female empowerment symbol and remained one until her passing in 2015.

Judy Landers

Celebrities meeting their own celebrity crushes happens more often than you’d think. When Judy Landers appeared on “The Tonight Show” in 1979, she shared that meeting him was a fantasy fulfilled. Why? Because she was infatuated with Carson.

Source: Reddit

Landers was starring as Stacks on “BJ and the Bear” when she came to interview with the late-night host. When pressed about her ability to operate a semi-truck, Landers confidently assured the audiences and Carson that she was able to drive a big rig.

Diane Lane

Diane Lane was newly 18 when she first went on “The Tonight Show.” She was on the show to promote the film adaption of “Rumble Fish” and refused to peck Carson on the cheek after being announced. Though, it seemed justified since he was 40 years older than her.

Source: Reddit

When Carson questioned Lane about how she celebrated her 18th birthday, she shared that she had spent the majority of the day taking care of her laundry. Knowing Carson’s history with double meanings, it’s safe to assume he was hoping for something juicier.

Farrah Fawcett

We will never forget the countless hours spent in the mirror, trying to recreate the Farrah Fawcett hairdo. She had numerous parts in movies and TV over the years but will forever be reminisced about for Jill Munroe in “Charlie’s Angels.”

Photo By Getty Images/Bettmann

Directly after choosing to leave her yearlong stint as Munroe, Fawcett went on “The Tonight Show.” During the interview, talk shifted to the show rating’s exponential increase. Fawcett hypothesized that the success of the show was due to the cast not wearing bras.

Robyn Hilton

Similar to actresses before and after her, Robyn Hilton made Johnny Carson eat humble pie. As a guest in 1974, her appearance was to promote the upcoming release of the comedy movie “Blazing Saddles.” However, Hilton was instead subjected to numerous offensive questions from the host.

Source: Pinterest

Carson shared with his guest that he believed her acting career as a result of being a beauty pageant contestant. Hilton’s swift and direct answer was that she “didn’t believe in beauty pageants,” hoping to put the host in his place for the rest of the interview.

Jayne Kennedy

Jayne Kennedy was one of a kind. The incredibly talented star made herself a household name by breaking both racial and gender barriers. Her long list of professional titles included dancer, model, sports broadcaster, actress, pageant winner, and television personality.

Source: Pinterest

Kennedy was an example for the world that women could thrive at least as much as men if not more! In addition to her three-year stint on “The Dean Martin Show,” Kennedy was one of the original female announcers for the NFL as the host of “Greatest Sports Legends.”

Marlo Thomas

Marlo Thomas claims that it was “love at first sight” when she first met daytime talk show host Phil Donahue. Keeping that in mind, the couple took around three years before they became married. The activist-actress first appeared on her future husband’s TV show in 1970.

Photo by Silver Screen Collection/Getty Images

The chemistry between the two was evident to everyone. Near the end of the show, Donahue told Thomas how much he enjoyed having her. Thomas responded that his girlfriend is a lucky woman. Who would have known that Thomas would turn out to be that lucky lady!

Connie Stevens

Most famous for playing “Cricket” in the detective show “Hawaiian Eye,” Connie Stevens was also a singer. She had several singles and albums, one of which was her most popular song, “Sixteen Reasons.” Though she was doing alright for herself in the US, she gained the most popularity overseas.

Photo by Ron Galella/Ron Galella Collection via Getty Images

She understood that even though she didn’t have only one big project in her name, she had done something treasured by people. In 1975 she was a guest on “The Tonight Show,” where she got the opportunity to reach a broader North American audience.

Goldie Hawn

Goldie Hawn attracted everyone’s attention with her piercing blue eyes. She made an appearance on the show very soon after having won an Academy Award for Best Supporting Actress. Audiences could tell that she was well on her way to international stardom.

Photo by Ron Galella/Ron Galella Collection via Getty Images

Her energetic personality and laughter were contagious; she was just at the beginning of her long, successful career. Hawn is now a decorated producer and actress, disproving the dumb blonde stereotype with one triumphant project after the next.

Dolly Parton

Johnny Carson was known for his filter-free questioning strategy, which more often than not made guests uncomfortable. The host of “The Tonight Show” frequently took things too far and acted foolishly during several interviews he had with the fabulous Dolly Parton.

Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

In spite of that, the award-winning country singer carried through making appearances on the show. Carson would waste their interview time commenting about her physical features rather than concentrating on her actual abilities and talents, both on-screen and stage.

Dolly Parton Part 2

“The Joan Rivers Show” was only on the air for four years, but it short-lived, having lasted only four years, and yet, it brought in some of the most famous celebrities in the industry. When Dolly Parton appeared as a guest on the show, an unlikely pair was created – the two women were complete opposites.

Source: theredlist.com

The polite Southern Belle speaking with the direct New Yorker; odds were good they were going to make it work. In 1993, Parton was a guest on the show, performing a selection of songs from “Slow Dancing with the Moon.” The savvy banter between the two women was unquestionably priceless.

Loni Anderson

Despite his problematic nature, Johnny Carson could still have the most stunning women in Hollywood as guests on his show night in and night out. During the late 70s and 80s, Anderson personified the role of the beautiful blonde that caught everyone’s eye.

Source: Pinterest

She was one of the most glamorous actresses of her time, and when she got a job with “WKRP in Cincinnati,” producers confessed she was hired for her beauty, not her skills. She reminded producers of a combination of Jayne Mansfield and Marilyn Monroe.

Shari Belafonte

Shari Belafonte is a singer, actress, and model, though she’s lesser known for these things. She is best known simply for having Harry Belafonte as a father rather than for her own accomplishments.

Photo by Joan Adlen/Getty Images

Before her stint on the popularized show, “Hotel,” Shari worked primarily as a production assistant and publicist behind the camera. After she gained some notoriety, she went on “The Merv Griffin Show.” Though she never outshone her father, she has continued working in the industry, booking numerous TV shows and movies.

Sonny & Cher

As their popular song “I Got You, Babe” became even more popular, the husband and wife pair took off to promote their music. They slowly, but surely, made their way around the TV talk show circuit. One of those performances was in 1979 on “The Mike Douglas Show.”

ource: Pinterest

Though their music was what initially drew fans, they were also loved for their dancing, outfits, and the love between them. Sonny and Cher gained enough fame to have their own TV show called “The Sonny & Cher Comedy Hour” on air from 1971-1974.

Charo

Her birth name was Maria del Rosario Mercedes Pilar Martinez Molina Baeza, but everyone recognized her as Charo. She was a talk-show veteran, making several visits on “The Merv Griffin Show,” “The Tonight Show,” and “The Mike Douglas Show.” Charo was a gifted singer, actress, and comedian.

Source: Pinterest

She had great difficulty when it came to speaking English fluently. The Spanish celebrity used her personable and enthusiastic personality to attract English-speaking audiences and soon became an icon with her “cuchi, cuchi” catchphrase.

The Time of Your Life

“The Time of Your Life” was on TV long before iconic sitcoms like “How I Met Your Mother” or “Friends.” With a cast of ordinary characters, the brief series had their characters hang out at their regular meet-up spot every week, making observations and talking with other patrons.

Source: howlingpixel.com

The show featured stars like Betsy Palmer and Jackie Gleason as the focal points of the series. Jackie Gleason’s character, Joe, acted almost as a judge as he evaluated the true essence of each newbie to their spot.

Cher

Much to the surprise of viewers, Cher came for a co-hosting gig on “The Mike Douglas Show” to do a week-long gig in 1979. The icon was able to show off her fresh fashion taste but also had a chance, and a stage, to perform a couple of her hit songs.

Source: Pinterest

Out of her song catalog, she performed “Take Me Home,” “My Song,” “Happy Was The Day We Met,” to name a couple. Cher had a motive in co-hosting the talk show; she wanted to prove that she was more than just Sonny’s assistant, and she did!

Deana Martin & Tina Sinatra

“The Dean Martin Show” had many exceptional guests, but none as unique as the segment where Frank Sinatra and Dean Martin were joined onstage by their 19-year-old daughters to perform a few songs all together.

Photo by Martin Mills/Getty Images

In 1967, their teenage daughters joined Frank and Dean for a performance of “Do-Re-Mi,” from “The Sound of Music.” As a well-received late-night show, they earned themselves the respect of being a fan favorite. They welcomed numerous guest and musical performances during their nine-year run.

Joey Heatherton

Joey Heatherton was a part of so many projects in the 1960s and 70s. Whether she was singing, dancing, or acting, many thought the talented star’s performances were surprising. Much of her dancing on TV consisted of controversial moves that got audiences talking.

Source: Pinterest

Of course, that wouldn’t deter Johnny Carson. He extended an invite to Heatherton onto “The Tonight Show” in 1963 to give him dance lessons. The response to the segment was so approving that a year later, Heatherton came for the first episode of “The Dean Martin Show.”

Dean Martin

Jerry Lewis was the man for comedy. Dean Martin was more known for being “The King of Cool.” Their styles worked well with each other, and the two beloved performers created one of the most iconic comedic teams of all time.

Photo by MDA/Getty Images

A “Rat Pack” member, Martin also boasted hosting duties over “The Dean Martin Show” and “The Dean Martin Celebrity Roast.” Spotlighted by one of Martin’s biggest songs, “Everybody Love Somebody,” his show aired 264 episodes over a nine-year span.

Elke Sommers

Elke Sommers managed to not only appear on countless late-night talk shows multiple times, but she also got herself a gig co-hosting one! The attractive actress from Germany spent a week in early February 1972 co-hosting “The Mike Douglas Show.”

Photo By Getty Images/Bettmann

Elke has hundreds of big and small screen roles on her resume and found great success for herself after World War II forced her to flee Germany. In the 1960s, she made the move to Hollywood and started finding work in both TV and movies.

Grace Slick

Who would have guessed that the lead singer of Jefferson Airplane would be the first person to drop the “F” word on TV. When Slick and the band performed in 1969 on “The Dick Cavett Show,” it was the day that pushed TV censors into complete panic mode.

Photo by Robert Altman/Michael Ochs Archives/Getty Images

They played their hit record “We Can Be Together,” which includes the infamous four-letter word. Slick’s slippage surprised Cavett, the studio audience, and viewers at home. This particular broadcast led to more censorship on TV.

Jean Shrimpton

Becoming an “it girl” is no laughing matter; it’s earned for good reasons. Shrimpton was alluring, charismatic, and dynamic – the quintessential British it girl. She was one of the most well-known women in the 1960s; her modeling and acting roles made her a sight to behold.

Photo by Jamie Hodgson/Getty Images

At the height of her fame, most of her time was spent on a screen, in an advertisement, or on the runway. In between gigs, Shrimpton was a guest on several of the late-night talk shows.

Judy Garland

In 1962, Judy Garland signed on for an interview at “The Tonight Show” stage for an interview with Jack Parr. The two had a very earnest and comical interview. Garland discussed her youth, birth name Frances Gumm, and the beginnings of her career, performing with her sisters.

Photo by Keystone/Getty Images

Before her celebrated role in “The Wizard of Oz,” the young actress would spend time perfecting her talent and performing alongside Liz Taylor, Mickey Rooney, among other notable names. It’s a lot of hard work to make it Hollywood, and Garland put in the work!

Jack Douglas & Reiko

Jack Douglas was most known for writing material for some of the biggest names in the industry. Douglas’s third wife, Reiko, was a regular on all of the late-night TV shows in the 60s and 70s. She cashed in on America’s obsession with anything and everything that was international and exotic.

Source: anosmia.info

Reiko was fluently bilingual in Japanese and English. Even though she knew fluent English, the Japanese-born woman acted like she knew very little English and wore traditional Japanese clothing to appear less assimilated. It was an intriguing sight to behold.

Suzanne Somers & Fred Astaire

When Suzanne Somers and Fred Astaire were interviewed on the stage together, no one would have thought they shared so much in common. The “Three’s Company star” and the most significant dancer in film were both versatile performers, both having appeared on TV and in film.

Source: Pinterest

They also had a shared interest in fitness for long-term maintenance over their appearance and athleticism. When they were both on “The Mike Douglas Show” in 1978, Somers and Astaire swapped their fitness regimens and pointers with the show’s host.

Dionne Warwick

The following statistic is unbelievable. Dionne Warwick had 69 songs on the Billboard Top 100 for over 30 years. This makes her only second to Aretha Franklin as the most charted female artist of all time. In addition to her award-winning songs, Warwick had countless collaborations with big names.

Source: Pinterest

When she appeared on “The Dean Martin Show,” she decided not to perform one of her hit songs. Instead, she chose to flex her acting chops in a comedy sketch alongside host Dean Martin. She wanted to prove she had other talents besides singing.

Zsa Zsa Gabor Part 2

Five years after Zsa Zsa Gabor won Miss Hungary, she made the move to the United States. Her European classiness and original style seal her fate as a sought-after actress. Unsurprisingly, she became heavily typecast and would find various roles working in TV, theater, and film.

Photo by NBC Television/ Getty Images

She soon became a recurring guest on late-night talk shows, and of course, found her way into gossip magazines. Gabor was known for her indulgent lifestyle and number of relationships; she was married 9 different times!

Joan Crawford

Joan Crawford was inarguably one of the most loved actresses in the 60s. She appeared on”The Merv Griffin Show” to promote her role in the psychological thriller, “Whatever Happened to Baby Jane?” Crawford received a standing ovation from the audience when she came on stage.

Source: Pinterest

Interestingly enough, despite the award-winning actress being a fan favorite, this was not the case when it came to her relationship with her castmates. This truth, among others, was later exposed in a tell-all book, “Mommie Dearest.”

Bette Midler

In his last show, Johnny Carson interviewed Bette Midler and Robin Williams as his guests of honor on May 21st, 1992. A noteworthy night in which Carson had guests contribute to the show, Midler made the sendoff that much more memorable.

Photo by Ron Galella/Ron Galella Collection via Getty Images

It was a nostalgic night for everyone, and Midler sang for the man of the hour with several of her hit songs. Carson’s final “The Tonight Show” segment was engaging for audiences; it would eventually win an Emmy Award.

Joan Rivers

Talk-show hosts and comedians will often say something so often; they become synonymous with the catchphrase. For Joan Rivers, her catchphrase was: “Can we talk?” The question originally came from her stint as a stand-up comedian; Rivers used it in place of saying, “let’s be honest.”

Photo By Getty Images/Bettmann

She figured out her way to the comedic roots of talking points that seemed difficult to discuss. To be honest, the late-night show host didn’t even notice she was saying it so much until her audiences began repeating it back to her!

Elizabeth Taylor

The name and the icon, Elizabeth Taylor, was one of the most well-known leading ladies in Hollywood, bringing in big box office numbers. It may seem like it was always success and fortune for Taylor, but she thought about walking away from the industry for a little while.

Photo by Jim Smeal/Ron Galella Collection via Getty Images

It was then that when she was offered a part in the star-studded cast of “Giant.” She starred in the movie alongside James Dean, Rock Hudson, and Dennis Hopper. As an actress and philanthropist, Taylor would make countless appearances on late-night talk shows, including several visits with Johnny Carson.

Jill Corey

Jill Corey found success in her teenage years singing on a live radio program in her hometown of Avonmore, Pennsylvania. She landed a record deal with a recording company and put out many hit songs and records in the early 1950s.

Source: jillcorey.net

On top of her many stage performances, Corey was also featured on several radio and television programs, including “The Tonight Show” with Johnny Carson. Corey had a unique style of dancing, singing, and sense of fashion. Her creative taste and girl-next-door attitude made her a fan favorite.

Joan Crawford Part 2

Johnny Carson officially took over the hosting duties on “The Tonight Show” on October 1st, 1962, becoming the third person behind the desk. For the following 30 years, Carson greeted the biggest names in Hollywood. During his debut night, Joan Crawford was featured as his esteemed guest.

Photo by William Lovelace/Express/Getty Images

Winning awards for her part in the psycho-thriller, “What Ever Happened to Baby Jane?” Joan would still be disgruntled towards her co-star, Bette Davis, who was nominated for numerous awards for her role in the film, while Crawford didn’t receive any.

Engelbert Humperdinck

It is a rare occurrence when a singer has three chart-topping songs in a single year, but for Engelbert Humperdinck, 1976 was the year he managed to do just that. His three hits reigned over the music charts in North American and the United Kingdom.

Photo by Daniel SIMON/Gamma-Rapho via Getty Images

Humperdinck earned a Grammy nomination and was considered the “most played juke-box record of the year.” Naturally, with success comes the promotion. Humperdinck made his rounds on the late-night talk show circuit, appearing on “The Dean Martin Show” and “The Tonight Show.”

Elvis Presley

The first host of “The Tonight Show,” Steve Allen, returned to the show in 1961 as a guest host. He introduced “The King of Rock and Roll” to the couch. Freshly released from his army service, Presley appeared on the show to perform his song, “Hound Dog.”

Photo by Michael Ochs Archives/Getty Images

Elvis was eager to return to the stage and return to performing. Serving in the military forced Presley to take a step back from the spotlight, which only increased his popularity. His absence made fans anxiously await his return.

Errol Flynn

As one of the biggest names in the 1930s, Flynn was one of Hollywood’s most popular stars. At the peak of his career, he was romantically linked with a slew of female celebrities, including Marlene Dietrich, Carole Lombard, and Lupe Valex, among a list of others

Photo via John Kobal Foundation/Getty Images

The star of “The Adventures of Robin Hood” was a veteran when it came to making promotional appearances. He was known to make his way multiple times through the late-night talk show circuit.

Jay Leno

Before hosting his own show, David Letterman would moonlight as the guest host for “The Tonight Show,” from 1978-1980. In 1982, Letterman would go to host his own show, “Late Night with David Letterman.” Hilariously enough, Letterman interviewed future “Tonight Show” host Jay Leno during one of his guest-hosting gigs.

Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

Leno was well known in the stand-up comedy circuit, garnering several minor parts in film and TV. When Carson retired in 1992, fans were convinced Letterman was next in line to host “The Tonight Show permanently,” but it turned out the role went to Leno, who hosted until 2009!

Emma Watson

The most uncomfortable moment on late-night talk shows that Emma Watson ever experienced occurred in 2012 on Jimmy Fallon’s show. She joined him for an interview and started off with a compliment on the ‘Halloween candy thing.’

Photo by Dave M. Benett/Getty Images

The ‘Halloween candy thing’ is a bit by fans who recorded their kids’ reactions when they were told that their parents had eaten their Halloween candy. It was brutal, hilarious, and Watson certainly enjoyed it. Watson was wholly mortified when she realized that Jimmy Kimmel was behind the bit, not Jimmy Fallon.

Nicole Kidman

Nicole Kidman was on “The Tonight Show” in 2015, being the first time since 2002 that she had seen Jimmy Fallon. The last time they met, a mutual friend tried to set the actress up on a date with Fallon at his apartment.

Photo by Theo Wargo/NBC/Getty Images for “The Tonight Show Starring Jimmy Fallon”

Fallon never realized it was a date or that she was available. She explained that she never pursued it because he ignored her by playing video games. Then she theorized that Fallon wasn’t attracted to women. Completely embarrassed, Jimmy snuck off his own stage.

Robin Williams

Robin Williams is iconic in every TV appearance he ever made. In 1998 he was interviewed by David Letterman. Letterman questioned him about his relationship with sitting president Bill Clinton, and the conversation was entertaining.

Source: Pinterest

When he started to promote ” Goodwill Hunting,” Williams spoke of the movie lovingly. He spoke about the engaging script, signing onto the project, and then meeting Ben Affleck and Matt Damon on set. Back before becoming stars, Williams joked about requesting to see some identification and if they had their parents’ permission.

Drew Barrymore

Recently, Drew Barrymore reflected on her 1995 performance on David Letterman’s show and concluded that the TMI moment was also a learning moment for her. She explained that because it was fun and she was only 20 years old; she didn’t regret it.

Photo by Ron Galella/Ron Galella Collection via Getty Images

Barrymore questions Letterman if he’d want her to dance on the table. Paul Shaffer played some jazz music. Before her dance on his desk concludes, she flashes him really fast and returns to sit down. Letterman couldn’t have been more genuine when he said, “I can’t thank you enough for that.”

Will Smith

Graham Norton gave Will Smith and his son Jaden Smith microphones, and they start freestyle rapping. Lighting up “The Graham Norton Show,” the “Men in Black” actor also had his personal DJ, Jazzy Jeff, on the show. Afterward, he and Jaden did a rendition of ” The Fresh Prince of Bel-Air” rap.

Photo by Ian West/PA Images via Getty Images

While all of this is happening, guest Heather Graham is dancing along. Will Smith’s largest surprise comes when Alfonso Ribeiro leaps onstage to do his famous Carlton Dance. Even Norton join the dance party – simply a great time for everyone.

Chris Pratt

When Chris Pratt was on “The Graham Norton Show” to promote “Guardians of the Galaxy,” when the host couldn’t avoid asking Pratt about his nudity. The actor instantly jumped into his naked stories, going as far back as stories from childhood when he’d get in trouble for undressing.

Photo by Isabel Infantes/PA Images via Getty Images

He assumed these habits could help his comedy work. When he pulled the prank to get a good scene take at “Parks and Recreation,” his flashing days were brought to a halting end. NBC sent him a letter that said he’s never allowed to do it again, which he framed.

Justin Bieber

This was back in 2012 when Bieber only had two tattoos, the second of which was still new and healing. This became obvious when Bieber screamed as David Letterman held the young artist’s arm to reprimand him for getting any additional tattoos.

Photo by Ethan Miller/Getty Images

“Believe,” the name of his new record was the new forearm tattoo. David Letterman continued the interview with the 18-year-old by giving advice about the importance of education, not getting any more tattoos, and voting in upcoming elections (despite him being Canadian).

Billie Eilish

Right from the get-go, Billie Eilish puts Jimmy Fallon on the spot. She recalls watching him on TV when she was a child. He was featured on “The Electric Company,” dancing and singing to songs. Fallon is embarrassed but pivots to talk about other stories from Eilish’s childhood.

Photo by Marc Piasecki/GC Images

Comedian Colin Quinn joins the pair for “True Confessions,” one of the games on “The Tonight Show.” Eilish discussed her upcoming “Where Do We Go” world tour. The multitalented 17-year-old also shared which songs she would be performing on SNL.

Russell Brand

Russell Brand was on “The Graham Norton Show” when he relentlessly interrupted Emily Blunt’s story about swimming with dolphins. She was explaining how close she was to a 6-foot-long shark. Brand interrupts dismissively, stating it’s merely a fish. Blunt, aggravated, asks him to stop diminishing her story.

Photo by Ian West/PA Images via Getty Images

He refuses to stop, continuing to interrupt her with mocking comments about how he has also been close to a fish. He doesn’t seem to care that she’s annoyed by his behavior. He had it coming to him when we found out that she ridiculed Brand backstage by mocking his Velcro belt.

Sofia Vergara

Sofia Vergara gets completely creeped out during an interview with Conan. She appeared on Conan O’Brien’s talk show in 2014. The host made her feel uneasy as soon as she sat down. In a bizarre voice, Conan tells his guest that he loves her.

Source: YouTube

Sofia tries to brush it off, but it’s evident that she’s uncomfortable. As the interview goes on, Conan continues to creep out Vergara by telling her he likes dancing with her boyfriend and begging her to laugh at his jokes.

Mark Ruffalo

They were talking about fears on “The Graham Norton Show” one night in 2015. Comedian Josh Widdicombe shared that he used to be a writer for “Dora the Explorer” magazine. It was his turn to share a personal fear. He began saying that he feared flying.

Photo by Ian West/PA Images via Getty Images

But then Mark Ruffalo abruptly suggested Widdicombe might be afraid of young girls. The actor immediately felt guilty about it. Ruffalo shamefully walked away after trying to offer an apology to Widdicombe by offering a gallant handshake.

Aziz Ansari

“Parks and Recreation” actor Aziz Ansari appeared on ” The Late Show” and went right into it by calling out the racism of CBS, in so many words. He also continued by calling out Stephen Colbert as the “bagillionth” Caucasian guy on TV.

Photo by Kevin Winter/Getty Images

Colbert sat stunned, fidgeting in his chair, distraught that CBS might come to check on him. Still stewing, Aziz bantered that someone is going to get in trouble for mispronouncing the title of his book. But Colbert countered with a chuckle and the hope that it turns out to be someone white.

Jaime Fox

Jamie Foxx appeared on ” The Graham Norton Show” in 2017. He performed a fantastic stand-up set while being on the red couch with Kristen Wiig, Judi Dench, and Steve Carrell. Discussing the hardships of dating at 49, he describes an interaction outside a bar in LA.

Photo by Isabel Infantes/PA Images via Getty Images

A car of young women screamed at seeing him, but it turned out they knew his daughter. In another incident when he was DJing, a couple of ladies in their 20s heard he was 49. He said they behaved like he revealed that he had a fatal disease!

Justin Timberlake

If you haven’t heard that Justin Timberlake and Jimmy Fallon are a BFF bromance, you have now. They have one of the most wholesome relationships of all the celebrities. On “The Tonight Show,” Fallon and Timberlake perform a sketch comedy skit.

Source: YouTube

Acting as teenagers at sleepaway camp, the friends get in trouble with their counselor for staying up late talking. It gets a little much when the two sing a duet of Alanis Morissette’s hit “Ironic.” They only go to bed after confirming that they’ll be best friends forever.

Lady Gaga

Nobody knows what’s going to happen when Gaga comes for an interview. To announce the release of her new album, “Born This Way,” she was dressed in a batgirl costume. The outfit included studded knee-high boots and a mask. A leather bikini was paired with a black leather jacket.

Source: YouTube

The diva encouraged fans to go out and buy her record. Discussing the NYC underground music scene where she was known to perform in a bikini, she asserted that it’s incredible what will happen when clothes are removed. Letterman seemed unphased. He was having a great time, loving her performance.

Shirley MacLaine

David Letterman didn’t enjoy his interview with Oscar-winner Shirley MacLaine, and, by the conclusion of the show, neither did she. She was there to promote her new movie, “Madame Sousatzka.”

Source: earthites.com

Letterman, who had been called the A-word by Cher in 1986, was coming off too strong. He questioned MacLaine harshly about her thoughts on past lives. She didn’t care to discuss it. Eventually, she exclaimed that Cher was correct to call him the A-word. It never improved from there. He finished the interview with the classic, “Oh, darn, we’re out of time.”

Jay Leno & Jimmy Kimmel

Jay Leno didn’t begin the feud between the two late-night show hosts, but he made it worse when he said that Jimmy Kimmel was mean, and that attitude affected his show’s ratings. Yikes! The fight began with Kimmel’s impression of Leno.

Photo by Kevin Winter/Getty Images

Jimmy Kimmel impersonated Leno for a whole episode of ” The Jimmy Kimmel Show.” Leno told the “Today” show that he hadn’t had prior issues with Kimmel. The feud ended in 2017 when Kimmel’s son went in for open-heart surgery. Leno called to offer his well wishes for a speedy recovery.

Tracy Morgan

Tracy Morgan rose to stardom from his time on Saturday Night Live, appearing in countless sketches during his run on the sketch comedy series. When ” SNL” stand-up comedian Morgan sat down next to Conan for an interview, he was promoting “The Last OG.”

Source: hollywoodreporter.com

Five years prior, on the late-night talk show, he was eccentric and shocking per usual. His interview answers were not known for their reservedness. Morgan referred to the president as a gang banger and suggested that he think about getting a teardrop tattoo.

Jim Carrey

Jim Carrey’s appearance on “The Tonight Show” in 1994 was memorable. At his ” Dumb and Dumber” peak, Carrey sat down with Jay Leno and immediately declared that he had hypnotized the whole studio audience. He commanded the audience to clap wildly at his word.

Photo by Kevin Winter/Getty Images

He claimed that his three consecutive number one hit movies are proof of this ability. It becomes stranger when he describes his alien abduction story and proves it by removing his shirt and drawing a sharpie line in a connect-the-dots map of his beauty marks, classic Jim Carrey.

Shaquille O’Neal

Jimmy Fallon tries wearing Shaq’s suit jacket in this interview. The host appears like his head shrunk, drowning in the suit that reaches past his knees. At the same time, Shaq tries to wear Fallon’s suit but can’t even fit his arm into a sleeve.

Source: thebiglead.com

Figures that the former Laker was there to promote a new line of suits at Macy’s. When Fallon asked if he’s ever turned down a promotional job, Shaq replied, saying he refused a fragrance line called DNA fragrance because they needed samples of his bodily fluids to develop it.

Kanye West

Every time Kanye West appears on a talk show, we buckle up. Kanye joined Kimmel on “Jimmy Kimmel Live” after a heated Twitter argument happened between them. Kimmel asked combative questions leading Kanye to state he adores when people are angry at him.

Photo by Johnny Nunez/WireImage

Kimmel started laughing when Kanye asked if Kimmel could picture him sharing with his publicist that he’s returning to TV. But the rapper-entrepreneur got deep, discussing why people are all characters on a life stage and that the only escape is to “break the simulation.”

Benedict Cumberbatch

Jimmy Fallon invited Benedict Cumberbatch to the show to play a game of Mad Libs. Cumberbatch chose assorted verbs, nouns, and adjectives to complete the sentences as Fallon recorded them. Then they acted out their finished scene.

Photo by Theo Wargo/Getty Images for NBC

If you’re a loyal Cumberbatch fan, this bit might’ve put that loyalty to the test. The skit was just uncomfortable and seemed to go on forever. At one point, the “Doctor Who” actor started singing a verse of “Baa Baa Black Sheep.” Fortunately, this marked the end of the bit.

Brad Pitt

Brad Pitt got a surprise present when he interviewed with Conan O’Brien to promote “Troy” (2004). O’Brien gifted the actor his 1992 Ford Taurus SHO. The manual sedan had been on the late-night talk show countless times because it was Conan’s first vehicle from university.

Photo by Dana Edelson/WireImage

We got to watch Pitt rev the engine and pull out of the parking spot during the appearance. O’Brien cautioned him not to exceed 35 mph because he said the bottom might fall off. He remarks that Brad and Jennifer are going to be incredibly pleased with the car.

Jennifer Aniston

The level of cringe in this interview exceeds everyone before it. When David Letterman welcomed Jennifer Aniston in 1998, she had come to promote her new film, “The Object of My Affection,” however, she ended up being the one to receive unwarranted affection.

Photo by James Devaney/WireImage

Jennifer, known for her beauty and role in “Friends,” puts up with Letterman’s increasingly awkward interview. He asks personal questions about her experience in the sauna. When he begins to nibble on one of her braids, she squeals. He doesn’t listen to her and continues sucking on her hair.

Will Ferrell

Not to be one-upped, Will Ferrell out creeps Letterman when he was on Conan. Donning full Ron Burgundy costume, Ferrell enters the stage playing his jazz flute. He introduces himself and announces that “Anchorman” is finally getting a sequel. The audience was delighted.

Source: Pinterest

Despite the initial joy, Conan was put off by Ferrell’s own explanation of what he intended with a rude innuendo. It’s too filthy to print here, but if you’re brave enough to watch the cringe-worthy segment, check out the clip!

Tom Hanks

Tom Hanks is America’s sweetheart for a reason, and the way he plays along in this late-night skit proves just how lovable he is. Hank was a guest in 2010 on Conan O’Brien’s new TBS show. From Conan’s desk, the two were pretending to whale watch.

Source: Pinterest

One of Hanks’s most notable movies is “Splash,” which inspired this sketch’s big splash. Gazing at the screen, Hanks genuinely enjoys whale life. He demonstrates his whale knowledge by sharing that a breach needs 40% of the animal to break the surface. In that exact moment, splash! Conan, miraculously, stays dry.

Jennifer Garner

In 2003, Jennifer Garner visited “Late Night” with Conan to promote “Daredevil.” The host, obviously wowed by the actress’s film history and the martial arts approaches she employed, is surprised when Garner informs him, he misused a word. “Snuck isn’t a word, Conan, and you went to Harvard, and you should know that.”

Source: Reddit

Conan, dejected, jokingly discloses he went to Harvard driving school. He didn’t forget this incident. Later in the segment, Conan brings out a dictionary and finds the word “snuck,” laughing deliriously like an evil villain.

Bill Maher

Stephen Colbert hosted fellow late-night host Bill Maher to the program during the 2016 presidential elections. It began normally, but Colbert asked Maher a specified question too many times. Maher screamed for Colbert to stop, but he wouldn’t. Eventually, the “Real-Time” host threatened to leave after the commercial.

Photo by Jeff Kravitz/FilmMagic, Inc

With each host sprinkling in ironic nicknames like “sweetheart” by Colbert and “baby doll” by Maher throughout the interview, the conversation continues. They attempt to be civil for the remainder of the segment. It concludes with Colbert requesting a better interviewee.

Norman Mailer & Gore Vidal

Dick Cavett wasn’t able to ignore that Norman Mailer and Gore Vidal were participants in a quid pro quo feud played out in magazines. So, he welcomed the two intellectuals for a debate on his talk show in 1971.

Photo By Getty Images/Bettmann

It was aggressive. At one point, Mailer condemned Vidal and the other panel members for being less competent than him. Cavett then suggested that Mailer might need another chair, the second being a place to put his alleged “giant intellect.” By the segment’s end, the audience loudly turned against Mailer.

Arnold Schwarzenegger

Bill Clinton shocked everyone as the first sitting president to appear on a late-night talk show. By 2003, Arnold Schwarzenegger would elevate politics and fame to an unprecedented level when he appeared on “The Tonight Show” with Jay Leno to publicize his bid for governor of California.

Photo by Kevin Winter/Getty Images

He shared with Leno that he supports the termination of the current governor, and then he announced his plan to replace him. Coming to no one’s surprise, yet somehow still unexpected, Schwarzenegger evoked the Terminator when addressing the California governor, “Gray Davis. Hasta la vista, baby!”