Top 20 Awkward Celebrity Interviews

Top 20 Awkward Celebrity Interviews

VOICE OVER: Phoebe de Jeu
Cringey, hostile, uncomfortable, humorous, and off-putting. These interviews run the gamut. For this list, we'll be looking at times when the tone or demeanor shifted during a celebrity interview. Our countdown includes Farrah Fawcett Spaces Out on “Letterman”, Mel Gibson's Gone to the Dogs, “The Dictator” Dumps Ashes on Ryan Seacrest, Kourtney Kardashian's Lost Connection, and more!


Welcome to WatchMojo and today we’re counting down our picks for the Top 20 Awkward Celebrity Interviews.

For this list, we’ll be looking at times where the tone or demeanor shifted during an interview. These moments can be cringey, hostile, uncomfortable, humorous or off putting.

What’s your most awkward interview? Let us know in the comments!

#20: Farrah Fawcett Spaces Out on “Letterman”

In 1997, the 50-year-old Charlie’s Angels star posed for Playboy and made her debut on “Late Show with David Letterman” at the Ed Sullivan Theatre. Fawcett opened with a few strong anecdotes about life in New York City, but swiftly drifted away from reality as Dave seemingly watched the trainwreck in slow motion. She giggled, described cryptic Central Park “walls” and had problems describing her own birthday celebration. The audience cackled in amazement and Farrah squirmed in confusion; but Fawcett always stuck to her guns that she was not on anything at the time of the interview. You be the judge.

#19: Courtney Love Crashes Madonna Interview

It was a moment that any music journalist dreams of: a one-on-one with Madonna. However, MTV’s Kurt Loder decided he needed more from the 1995 Video Music Awards post-show. After being pelted from below by what turned out to be a makeup compact, Loder brought Courtney Love up to join the party. The “Material Girl” instant expressed her concern and things quickly got weird. The Hole singer rambled on about science and catfights, while Madonna put on a fake smile as the MTV host was visibly filled with regret. When it was all over, Love face planted into both the stage and infamy.

#18: Paris Hilton Walks Out

This rocky 2011 interview started off light with nosy cats interrupting the scene, but soon became prickly when Kim Kardashian entered the conversation. ABC’s Dan Harris spoke with Paris Hilton about her numerous stalkers and ditzy public persona, but encountered a severe case of stink eye once he questioned the fleeting fame of the entrepreneuse. Hilton looked off camera for guidance, while Harris threw up a white flag with a knowing smile. The two hugged it out, but ABC ultimately mocked Ms. Paris during their intro segment to the piece.

#17: Mel Gibson’s Gone to the Dogs

Do NOT…we repeat DO NOT…bring up the past to Mel Gibson. After his 2006 drunk driving arrest, the actor took several years off but returned to the spotlight for the 2010 thriller “Edge of Darkness.” During an interview with veteran entertainment reporter Sam Rubin to promote the flick, Gibson took offense when his alleged anti-Semitic tirade was brought up, and shot back at the reporter with a sharp retort [“Do you have a dog in this fight?”]. Some interpreted the comment to mean Gibson was accusing Rubin of a bias against him due to his own Jewish heritage. However, Rubin politely smiled but later expressed his anger, while Gibson moved on to more equally awkward interviews.

#16: Mistaken Identity


It could have just been an honest mistake but Samuel L. Jackson was having none of it. When asked about the response to a Super Bowl commercial Jackson is at first confused before realizing that the reporter has mixed him up with Laurence Fishburne. For his part the reporter profusely apologizes but Jackson doesn’t let up. He questions his credibility and proceeds to list other famous black actors who are spokespeople for other brands. The reporter desperately wants to move on to talk about “Robocop” but Jackson keeps going. We have to hand it to Jackson for expert roasting in response to this gaffe.

#15: No Time for Jokes

“The Joy Behar Show” (2009-11)

Reality TV is frequently characterized as fake but sometimes things get real, a little too real. Shannon Tweed and Gene Simmons made an appearance on Joy Behar’s show to promote the new season of their reality show where a poorly timed joke brought everything to a standstill. Tweed is clearly not having it due to some questionable behavior from Simmons rock n roll lifestyle. Behar is legit confused by the interaction between the guests.After Tweed walks off the set Simmons is upset with the angle Behar went with leaving the host having to defend herself. Sometimes you just have to read the room, Gene.

#14: Cara Delevigne Is Tired?


Sometimes people are on a different vibe and it’s something the hosts of a local news morning show don’t seem to understand. They start off asking Delevigne if she’s had time to read the book for the movie “Paper Towns” she’s there to promote. She gives a sarcastic answer, eliciting laughter from the hosts. Things go downhill from here as one of the hosts point blank calls out Delevigne for not appearing excited enough and another commenting that she seems irritated. She handles the situation as well as she can while they agree to end the interview. Once over, the hosts continue to take digs at her. If they thought that insulting someone to their face would improve things, they were wrong.

#13: “The Dictator” Dumps Ashes on Ryan Seacrest

At the 2012 Academy Awards, Sacha Baron Cohen showed up in-character and accompanied by sexy female guards for his red carpet arrival and made it rain all over a surprised Ryan Seacrest. Cohen was promoting his latest film “The Dictator,” and was carrying an urn supposedly filled with the ashes of recently deceased North Korean dictator Kim Jong-il. Always a professional, Mr. Seacrest handled the incident rather well, as Baron Cohen retreated with a few words of advice. In the end, Seacrest looked like “Scarface” but he gained the admiration of a giddy Giuliana Rancic.

#12: Jian Ghomeshi vs. Billy Bob Thornton

The American country-rock band The Boxmasters formed in 2007 and were fortunate enough to appear on Canada’s acclaimed “Q” radio show just a couple years later. Unfortunately for host Jian Ghomeshi, the group’s most famous member, Billy Bob Thornton, took offense when his extensive background in film was mentioned. For almost half of the 13-minute interview, Thornton gave cryptic answers while his band mates looked like they had just seen a puppy run over by a semi. Even though Thornton’s fame brought attention to the band, he made it clear that said fame shouldn’t be discussed. A classic Hollywood move.

#11: Britney Spears Brought to Tears

“Primetime” (1989-2012)

Billed as no holds barred, interviewer Diane Sawyer had no issues coming down on Spears for some of the provocative aspects of her public image. While discussing some of the then recent bad PR Spears received at various public events, Spears breaks down crying and requests a pause. They move onto discussing Spears' relationship with Justin Timberlake and Sawyer presses her on her responsibility in that relationship’s end. It’s clear Spears is uncomfortable and even directly calls it out.

#10: The Carrot Top of Interviews

This interview, promoting “Now You See Me”, doesn’t get off to a good start after Eisenberg takes issue with the way Puga casually refers to fellow co-start Morgan Freeman. Things just get more awkward as the interview goes on. Eisenberg notices Puga has writing on her hand and questions her about it asking if she’s hiding questions while also taking a slight dig at her ability to remember simple questions.Puga asks him to perform a card trick he learned, which he agrees to do. He then states that she’s the Carrot Top of interviewers. Yeesh. There’s definitely a nervous energy here and it is not helping things.

#9: Martin Bashir Interviews Michael Jackson

Over the course of eight months from 2002-03, the King of Pop was followed and interviewed for a British documentary, ostensibly to see what his day-to-day life was like. However, MJ made the unfortunate admission that he slept in bed with children. Journalist and host Martin Bashir expressed his concerns to Michael Jackson, who defended his actions by citing “love.” Jackson recalled his experiences sleeping with Macaulay and Kieran Culkin, and actually spoke like a child as he remembered hot-air balloon excursions at Neverland Ranch. The entire documentary stunned audiences and ultimately led to a sexual abuse trial. Michael Jackson was found innocent of all charges.

#8: Robert Downey Jr. Nopes Out

Channel 4 News

While discussing the character of Tony Stark following the release of “Age of Ultron” goes well enough until things start to veer into Downey’s personal life. When Guru-Murthy brings up a quote Downey gave in the past following some legal trouble, he uncomfortably looks around the room but entertains the question. It’s clearly an avenue Downey doesn’t want to go down and tries his best to politely give Guru-Murthy an out and move on to something else. The whole tone of the interaction changes as Guru-Murthy continues to focus on Downey’s personal life and his relationship with his father. At this point Downey’s had enough and leaves quipping it was a little too Diane Sawyer for his liking.

#7: Crispin Glover’s High Kick

“Late Night with David Letterman” (1982-93)

From the start Glover appears to be confused and disoriented as Letterman asks him basic questions about where he’s currently living. In addition to his strange behavior Glover is also sporting a wig, an odd choice of clothes and shoes. In fact he’s heckled by the audience about his choice of footwear. From there he becomes increasingly frantic while Letterman is trying to figure out what’s going on. Glover then challenges Letterman to arm wrestle followed by a high kick that was a little too close for Letterman’s liking. It’s possible Glover was in character for a film that wouldn’t be released for a number of years but he’s never revealed his intent behind the appearance.

#6: Kourtney Kardashian’s Lost Connection

“Today Extra” (2012-)

In 2016 while in Paris, Kim Kardashian was robbed of several million dollars worth of jewelry by several masked men. Following that terrible ordeal, sister Kourtney Kardashian made an appearance on an Australian morning program to promote a skin care line. The hosts ask her how Kim is doing following the traumatic event and right as she’s about to respond she’s interrupted by someone off screen. The hosts are left bewildered as Kardashian doesn’t respond to their questions. Dead air follows as they figure out what to do while smiling at the camera. They surmise that someone must have told Kourtney not to answer the question. She eventually explains that a connection was lost and gives an update to how the family is doing.

#5: Wendy Williams Drags Draya Michele

“The Wendy Williams Show” (2008-22)

Draya Michele sat with Wendy Williams to talk about her role in the reality show “Basketball Wives LA”. While the two did end up talking about the show, it probably wasn’t in the way Michele was planning. From the get go Williams is on Michele about her previous work as a dancer and how many basketball players she’s been with. Williams even questions if Michele had been with 3 players in one night. Tepid audience responses suggest that many in the studio didn’t really know how to react with Williams having to remind the audience that her line of questioning makes sense if you’ve seen “Basketball Wives”. Michele for her part is very tempered in her responses despite Williams’ line of questioning.

#4: An Unwanted Kiss


While promoting the release of their new-at-the-time album “Blood Sugar Sex Magik”, Flea and Anthony Kiedis stopped by MuchMusic and spoke with VJ Erica Ehm. The Peppers seemed to be in a mood where they seemed contemptuous about playing in Canada stating they only sold shows because the venues are no bigger than Flea’s bathroom.Ehm engages with them honestly and earnestly throughout despite their demeanor. It becomes incredibly awkward when Kiedis decides he wants to give Ehm a kiss despite her pleas for him not to do so. She chastises him afterward saying she’ll be blamed for what happened. Later on Kiedis asks her what color her underwear is. These antics wouldn’t fly today and they shouldn’t have then.

#3: Tarantino Shutdown

An acclaimed journalist who’d been in the biz for decades, Krishnan Guru-Murthy of Britain’s Channel 4 received a surprise one day when interviewing Quentin Tarantino. There to promote his new film “Django Unchained,” the director shunned his questions about violence – actually, shunned is an understatement. It’s no secret that Quentin Tarantino’s made some of the bloodiest films over the past 25 years, but he unleashed the crazy eyes once the interviewer asked about the real-life implications of such violence. Guru-Murthy chuckled and Tarantino torched him with a verbal smackdown that left the dapper host both confused and amused.

#2: Charlie Sheen is #Winning

The Internet went wild in 2011 as one of Hollywood’s most exuberant personalities officially… well let’s say, took a break from reality. In an at-times hilarious and but also troubling interview with Andrea Canning, Charlie Sheen explained that he wasn’t bi-polar but rather “bi-winning” and had “tiger blood,” among his many quotable quips. The ABC host pressed the actor about his relentless partying, which led Sheen to boast that his antics would make Frank Sinatra and Keith Richards looks like “droopy-eye armless children.” Social media went crazy and so did Sheen.

#1: Tom Cruise Jumps the Couch

Some actors fake tears and some actors fake excitement. It’s what they do. So, was it a huge surprise when Tom Cruise went nuts on “The Oprah Winfrey Show” in 2005 and declared his love for Katie Holmes? Right around the same time Cruise had lost his longtime publicist and was also boasting about his knowledge of psychiatry, the digital age was being revolutionized by outlets like TMZ and YouTube, which made Cruise’s couch jumping an instant viral hit. Perhaps he was simply promoting his next film “War of the Worlds,” but his goofy appearance made him an instant punch line. It was awkward and undoubtedly awesome.