The Most Cringe-Worthy Celebrity Interviews Of All Time

An actor has a movie out, a singer has a new album to promote, a reality star has another life story to flog, a comedian has standup tickets to sell, an ex-porn star has an alleged tale to tell about an allegedly adulterous world leader. So what do they do?

Naturally, they – or at least their press agent or studio – line up the interviews and get ready for a whirlwind tour of scoop-hungry journalists looking to poke a story out of them.

In the 21st century, it’s become part and parcel of the celebrity lifestyle.

They do the rounds on radio, they sit down and talk to all the big magazines and – most importantly for those looking for some potential car crash viewing – they go on TV and they give an interview that may get people talking for all the wrong reasons.

When celebs are on the promotional circuit, they find themselves under pressure to repeat the same blurb over and over again, being asked the same questions probably 20 times in a single day, by one news channel and then the next.

It’s no surprise, then, that sometimes celebrities can lose their cool. An interviewer will ask something the interviewee deems silly or inappropriate and they will completely go off the roof.

Live or not, a car crash moment of television is in the can, ready to air and almost guaranteed to go viral.

In honour of all those brave celebs who have heroically fallen on the great battlefield of the awkward interview, we’ve decided to count down the 25 most cringe-worthy celebrity interviews of all time.

Watch below as 25 our most beloved A-listers (and a few Z-listers) go completely off the rails.

25. Paris Hilton walks out on Dan Harris

Dan Harris was conducting an interview with socialite, businesswoman and media personality Paris Hilton when she decided he didn’t like one of the questions he asked.

He is talking about the ratings on her show being low, and asks ‘do you ever worry about your moment having past?’

Paris looks off camera towards her publicist, clearly unhappy.

‘You wanna wrap up?’ Dan asks, and off Paris goes. He clearly hit a nerve.

24. Burt Reynolds v.s Marc Summers

Back in 1994, Marc Summers, the host on a Nickelodeon game show, decided to take on the actor Burt Reynolds.

Summers made a crack about Reynold’s divorce. The Smokey & the Bandit star had recently split from Loni Anderson.

He threw a cup of water over Summers, who soon threw one back.

Host Jay Leno tried to steer clear of the carnage, but even he got hit by pie shrapnel.

23. Jim Rome v.s Jim Everett

In this incident, ESPN2 host, Jim Rome, was interviewing former LA Rams quarterback Jim Everett.

Jim kept pushing the wrong buttons when he repeatedly called him ‘Chris Evert,’ a female tennis champion.

“If you call me Chris Evert to my face one more time,” Everett said, wagging a finger at Rome, “you better take a station break.”

Rome decided to take his chances and called him Chris one more time. The quaterback upturned the desk and launched at the host.

22. Courtney Love hijacks an interview with Madonna

Sometimes in life, you just need some attention. In the interview you’re about to see, Courtney Love felt like she wasn’t getting enough attention.

So much so, that she decides to hijack an interview with Madonna.

The pop princess was being interviewed at the 1995 MTV VMA awards when Courtney decided to start launching things up onto the stage from her handbag.

The host promptly invites her up onto the stage and she gets her own mic. It’s fair to say that Madonna didn’t look too impressed and leaves shortly after.

21. Shannon Tweed v.s Gene Simmons

This one is particularly awkward and painful to watch.

Shannon Tweed was on Joy Behar’s show with her partner, Gene Simmons.

It’s clear from the beginning that the pair weren’t getting on very well.

The straw on the camel’s back broke when Joh Behar asked “How’s your back, Gene?”, in reference to his sex life.

This was one thing too much for Shannon, and she proceeded to walk out with Gene trying to win her back around again.

20. Sacha Baron Cohen Spills Ashes on Ryan Seacrest

Ryan Seacrest probably only has himself to blame for this one, after interviewing Baron Cohen on the red carpet at the 2012 oscars.

The actor was carrying an urn, explaining they contained the ashes of recently deceased North Korean leader Kim Jong-il.

“It was his dream to come to the Oscars and to be sprinkled over the red carpet and over Halle Berry’s chest,” Cohen explained.

The ashes ended up being “accidentally” dumped on Seacrest’s jacket instead.

19. Cara Delevigne’s ‘exhausted’ interview

The anchors of Good Day Sacramento were not too impressed with the model and actress Cara Delevinge.

She appeared on the show in 2015 to promote her film Paper Towns.

She looked quite unenthused to be there, but perhaps is didn’t justify the grilling from the hosts.

They said she seemed “a bit irritated,” but Delevinge replied with “No, I think it’s just you.”

18. Joan Rivers v.s Fredricka Whitfield

If you’re going to interview and grill an 81-year-old comedy legend with a famously sharp tongue, you should be prepared for some rebukes.

When a CNN interviewer got a bit too critical and negative with Rivers, she responded in exactly the way you might expect.

She stormed off the set and continued to spout out expletives off camera.

17. Charlie Sheen’s “Winning Interview”

Perhaps one of the most infamous interviews in recent time is Charlie Sheen’s “winning” interview.

He gave many crazy interviews during his 2011 Tiger Blood period, but perhaps the one on Good Morning America is his best.

In it, he assures the host that he is not bi-polar, he’s bi-winning.

He’s been “bangin’ seven-gram rocks and finishing them because that’s how I roll.” He blinked and cured his brain. “Can’t is the cancer of happen.” Compared to him, stars like Frank Sinatra and Mick Jagger “just look like droopy-eyed armless children.”

16. Jessie Eisenberg v.s Romina

Perhaps the most tricky interview to get through of all time, is that of Jessie Eisenberg v.s blogger, Romina.

Some awkward lines include: “I said your name into camera, what more do you want.”

“You are like the Carrot Top of interviewers.”

My favourite though definitely has to be from Romina: “I want a magic trick, so we can wrap this up.”

The girl clearly wasn’t impressed.

15. Joaquin Phoenix vs David Letterman

If an actor goes on a talk show as a monosyllabic, possibly depressed version of himself for a prank without ever telling the host it’s a prank, is it still a prank?

That question is at the heart of the painfully awkward interview David Letterman endured with Joaquin Phoenix back in 2009, wherein Phoenix apparently came dressed for a funeral and subsequently mumbled uncomfortably for nine minutes.

Really, Phoenix was just playing a character, the exaggerated and obnoxious celebrity ‘Joaquin Phoenix’, for his 2010 mockumentary I’m Still Here.

Letterman wasn’t aware of this at the time, however, something that was addressed when Phoenix returned to Letterman as a much brighter version of himself a year later and apologised.

14. Jack Nicholson crashes Jennifer Lawrence’s Oscar win interview

Jennifer Lawrence looked understandably thrilled to win the Best Actress Oscar in 2013 for her performance in Silver Linings Playbook.

Arguably the most incredible thing to happen to Lawrence on that night, however, came after the ceremony.

During her post-Oscar win interview with ABC News, Lawrence was interrupted by prowling 75-year-old lothario Jack Nicholson.

“You look like an old girlfriend”, Jack tells Lawrence live on air. How about a new girlfriend? she asks. His response: “I’ve thought about it…I’ll be waiting.”

13. Jim Carrey declares “There’s no meaning to any of this” at New York Fashion Week

Before he retreated indoors and started making disturbing political paintings for a living, the first sign Jim Carrey had gone off the deep end came in 2017.

It was in September of that year that Carrey rocked up to New York Fashion Week, announced “there is no ‘me'” and generally rambled to reporter Catt Sadler like a teenager who’d just read Noam Chomsky for the first time.

Circling Sadler like a shark, Carrey told the E! host he was there at NYFW because “I wanted to find the most meaningless thing I could come to”.

It only got more intense from there, with Carrey asking “Do you believe in icons?”, telling Sadler “I don’t believe that you exist” and cheerfully declaring “we don’t matter”. Ace Ventura, everybody!

12. Mel Gibson calls a reporter an “a**hole” live on air

It was 2010, and Hollywood pariah Mel Gibson was hoping to make a comeback with his new movie Edge of Darkness.

Not everybody, however, was willing to let Mel off the hook so easy during the disgraced star’s promotional tour.

Appearing on Chicago’s WGN-TV with immediately obvious crazy eyes, Mel never looked like he was going to take kindly to WGN reporter Dean Richards’ questions, especially not when talk turned to Gibson’s infamous antisemitic tirade in 2006.

Unapologetic, “move on dude” was Gibson’s response to Richards’ questioning, before ending the interview with a simple “a**hole”, prompting a double eyebrow raise from Richards.

11. David Blaine vs GMTV

Along with impossible tricks and death-defying stunts, street magician David Blaine has built his reputation on being an unknowable eccentric.

It was no surprise, then, that Blaine turned out to be an awkward interviewee when he appeared on Britain’s GMTV live in 2001.

Ostensibly on the show to promote a new show, Blaine at first simply sat silent and stared at host Eamonn Holmes.

Before Holmes could cut the interview early, Blaine would show his palm – on which was drawn an eye (“Protection from death”) – and laugh demonically at his interrogator.

10. Samuel L Jackson does not appreciate being mistaken for Laurence Fishburne

Samuel L Jackson has spent near his whole career correcting people who wrongly assume he’s Laurence Fishburne, and he’s just about had enough of it.

This became evident in 2014, when KTLA reporter Sam Rubin mistook Jackson for an actor who starred in a recent Super Bowl ad – not realising it was actually Matrix star Fishburne.

What followed was four minutes of one of the most uncomfortable celebrity interviews in recent history, with Jackson refusing to let Rubin forget his error.

“We may be black and famous, but we don’t all look alike!” yelled Jackson, before helpfully explaining to Rubin which commercials star which ‘other black guys’.

9. #TimesUp for Ben Affleck

Back in 2004, there was an interview that Ben Affleck gave for a Canadian entertainment show in which the Argo actor-director drunkenly groped the female interviewer for four minutes straight.

This was pre-Harvey Weinstein, so everyone at the time simply ignored the clip and moved on with their lives. There’s just one thing about the internet, though: it never forgets.

The interview, which resurfaced in 2017 as rumours of Affleck’s past bad behaviour circulated, sees the star sitting his interviewer on his knee and suggesting she go ‘topless’.

Affleck obsesses over his interviewer’s “suspiciously firm” breasts throughout the ‘interview’, going on to ask why she isn’t “getting them t***ies out” as he flirts in the creepiest French accent he can muster.

8. Sean Connery tells interviewer why he slaps women

In 1965, at the height of his James Bond fame, Sean Connery told Playboy magazine: “An open-handed slap is justified…If a woman is a bitch, or hysterical, or bloody-minded continually, then I’d do it.”

Still, times change and so do people – surely, when confronted about his words 22 years later, Connery would show some remorse? Actually, no.

In a 1987 interview with Barbara Walters, much to her surprise, Connery simply doubled down on his previous comments, telling her “I haven’t changed my opinion.”

Saying he doesn’t “think it’s that bad” to hit a woman “if it merits it”, Connery calls a slap warranted if she provokes him by arguing with him for too long.

7. James Brown won’t talk about his domestic violence charges, would rather sing

From 1987 onwards, James Brown was arrested on domestic violence charges on multiple occasions.

In 1988, following Brown making bail after he was accused of shooting at his wife as she drove from their house, Brown went on CNN to discuss his upcoming tour.

Of course, the interviewer instead asked questions about the latest allegations regarding Brown, all of which he batted away by singing his own songs at her.

Acting bizarrely even for him, Brown smiles throughout all anchor Sonya Friedman’s questions, his only real response to questions about his behaviour being to sing This Is A Man’s World as a way of explanation.

6. Tom Cruise vs Oprah’s couch

If we can pinpoint the turning of public opinion of Tom Cruise to a single moment, it’s this.

Having recently publicly confirmed his relationship with Katie Holmes, Cruise in 2005 went on The Oprah Winfrey Show to talk it out.

Only, Cruise wasn’t really there to talk; he was there to bounce around the room like a toddler at an additive-fuelled birthday party.

Looking like he was having some kind of manic episode, Cruise would profess his love for Holmes by jumping on Oprah’s couch, pulling power poses and laughing maniacally, as if possessed by whatever Scientology’s equivalent of the Devil is.

5. Harry Belafonte vs the lure of sleep

In a long and varied career, legendary singer-actor-activist Harry Belafonte has won an Oscar, an Emmy, a Tony award and a Grammy.

Basically, such achievements mean Harry Belafonte can do pretty much whatever the hell he wants, up to and including falling asleep in a live TV interview.

In 2011 – when Belafonte was 84-years-old, let’s not forget – KBAK-TV had the King of Calypso booked on the show to talk about a new HBO documentary about his life.

Unfortunately, the interview never actually happened, unless you count the KBAK anchor screaming at Belafonte in an effort to get him to wake up from an apparent daytime nap.

4. Billy Bob Thornton just wanted to talk about the music

Remember Billy Bob Thornton’s hitman character in the first season of Fargo? Interviewing Billy Bob Thornton is like that.

At least, that’s how it appeared to be in 2009, when an interview with Billy Bob on Q Radio went spectacularly wrong.

BBT was there to discuss his musical output with his band The Boxmasters, but he took offence to host Jian Ghomeshi bringing up his acting career in his intro, as opposed to just focusing on the music, man.

Thornton would largely sit and glower for 12 excruciating minutes, with Thornton’s default response to Ghomeshi’s perfectly understandable questions quickly becoming: “I don’t know what you mean.”

3. Tom Hardy doesn’t appreciate questions about his sexuality

Interviewing king of cinematic brooding Tom Hardy doesn’t look easy at the best of times, but throw in a question about the Bane star’s sexuality and it can really go to pieces.

This is what one reporter found in 2015, at the Toronto film festival, where Hardy was in town to promote the gangster movie Legend.

Drawing on Hardy’s past interviews on his apparent bisexuality, a Daily Xtra reporter asked Hardy: “Is it hard for celebrities to talk to the media about their sexuality?”

This provoked a sullen look from Hardy, who asked “What on Earth are you on about?” before moving the press conference swiftly along.

2. Meg Ryan vs Michael Parkinson

After decades in the business, Michael Parkinson became a legend of the interviewing circuit and an institution in the UK.

One person who did not feel reverence towards Sir Michael, however, was Hollywood actress Meg Ryan.

From the off, Parkinson’s 2003 interview with the When Harry Met Sally star had a tetchy vibe, like the two weren’t quite able to see eye-to-eye.

After Parkinson accused Ryan of being “wary of journalists”, the interview was evidently unrecoverable, leading to Ryan telling Parkinson to “just wrap it up”.

1. Robert Downey Jr vs Krishnan Guru-Murthy

“Clown”. “Bottom-feeding muckraker”. “Syphilitic parasite”. These are just some of the words Robert Downey Jr used to describe Channel 4 journalist Krishnan Guru-Murthy.

For those not in the know, Guru-Murthy is the British journalist who once famously had ‘his butt shut down’ in an interview with an irate Quentin Tarantino.

This same reporter, not long after his confrontation with QT, also managed to make Robert Downey Jr, one of the most beloved Hollywood stars, walk out of an interview early.

Starting the interview looking tired after yet another Marvel press tour, Downey took offence to Guru-Murthy asking about his history with drugs and whether prison had changed his politics.

Downey responded by giving Guru-Murthy the Frank TJ Mackey treatment: stare and silently judge, before cutting the interview short.