These Awkward Celebrity Interviews Will Make You Squirm

Journalism at its most cringeworthy.

This month marks the 10th anniversary of Tom Cruise’s infamous couch-jumping interview on The Oprah Winfrey Show, where he proclaimed his love for (now) ex-wife Katie Holmes. It’s the king of awkward celebrity interviews, if we’re being honest. However, Cruise’s weird appearance is just one of many A-list interviews that went awry. Check out these nine beyond bananas sit-downs.

  1. Robert Downey, Jr. and Krishnan Guru-Murthy, 2015

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    Downey, Jr. recently made headlines for walking out of an Avengers: Age of Ultron junket interview when the journalist brought up personal questions about the actor’s tumultuous past. After Guru-Murthy mentioned Downey, Jr.’s previous addictions, the movie star asked, “What are we doing?” and quickly excused himself. “It’s just getting a little Diane Sawyer,” he added before leaving the room. Yikes.

  2. Madonna and David Letterman, 1994

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    When the Queen of Pop sat down with Letterman at the end of her Erotica era, she couldn’t help but drop several F-bombs and talk about peeing in the shower. (It starts not even a minute into the exchange when Madge tells Dave, “You are a sick f—k.”) In 2009, Madonna alluded to the interview when she visited Letterman and said, “I think I may have made a fool of myself once or twice too on your show…I think it may have had something to do with joint I smoked before I came on.” Hugs not drugs, kids.

  3. Tom Cruise on the red carpet, 2006

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    At an international Mission: Impossible III premiere, Cruise was giving a pleasant interview when it appeared someone from the journalist’s crew squirted him with a water gun. What transpired was a tense confrontation where Cruise repeatedly asked (with a creepy smile), “Why would you do that?” Cruise also said, “I’m here giving you an interview and answering your questions and you do something really nasty. You’re a jerk” before walking away. Can’t say we disagree.

  4. Carrie Prejean and Larry King, 2009

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    The former Miss California USA, who got flack for denouncing same-sex marriage during the 2009 Miss USA pageant, sat down with King to discuss her book Still Standing: The Untold Story of My Fight Against Gossip, Hate, and Political Attacks. However, Prejean shut down after King asked why she settled her lawsuit against pageant officials after claiming they discriminated against her religion. King pursued the issue because he felt it didn’t violate Prejean’s confidentiality agreement, but she simply said, “You’re being inappropriate” and dismissed his questions. The climax came when Prejean took off her mic after King accepted a phone question from a viewer (which apparently wasn’t cool with her publicist). “I think that you are being extremely inappropriate right now, and I’m about to leave your show,” she said. Groan.

  5. Paris Hilton and Dan Harris, 2011

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    After the ABC News journalist asked Hilton, “Do you ever worry about your moment having passed?” (which, yes, is a low-blow question), the heiress scoffed toward her her publicist and walked off camera. The next shot you see — after hearing her say, “Well, I don’t want all of this being used” — is Hilton taking a deep breath, throwing on a 100-watt smile and giving a seemingly rehearsed answer to Harris’ question: “I’ve been in this business for 15 years now, so it’s been a very long time, and just like any other businessperson or someone in the industry, it’s always important to reinvent yourself and come up with new projects.” A perfectly harmless boring response.

  6. Heidi Montag/Spencer Pratt and Al Roker, 2009

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    Following their dramatic departure from NBC’s I’m a Celebrity…Get Me Out of Here!, Speidi sat down with Roker for a very terse interview oozing with judgment. Roker point-blank asked Montag, “Are you proud of all of this?” and ended the sit-down by letting Pratt know many people think he’s a jerk. On the interview, Montag told Ryan Seacrest, “I was shocked at how rude he was. I was crying afterwards…” So much for objectivity. (Granted, Speidi is pretty insufferable and Roker’s only human. We’ll give him a pass.)

  7. Bruce Willis/Mary-Louise Parker and Jamie Edwards (Magic radio station), 2013

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    But we won’t let Willis slide for being a total A-hole to this poor Magic radio station reporter during a Red 2 junket interview. The hunky action star was dismissive of Edwards’ run-of-the-mill questions at first, but he soon became just mean. As the journalist tries to save the flailing interview by asking questions about the film — which reporters are supposed to do during a junket — Willis cracks, “I’m thinking about driving right now. I can hardly keep my mind on this interview. I’m thinking about driving somewhere.” Willis tops off his behavior by sarcastically telling Edwards, “Go ahead. You have some great questions there, Jamie.” Geez. How dare Edwards do his job!

  8. Quentin Tarantino and Krishnan Guru-Murthy, 2013

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    Guru-Murthy makes our list twice, this time for his chat with Tarantino while promoting Django Unchained. When asked about the relationship between film and IRL violence, the eccentric director refused to give a direct answer because he’s “already on the record” about that subject. (He doesn’t see a correlation, in case you were curious.) Even still, it didn’t stop Guru-Murthy from prying more into the topic, only to have Tarantino shoot him down with answers like, “It’s none of your damn business what I think about that” and, “This [interview] is a commercial for the movie.” Simmer down, Q.

  9. Kanye West and Sway, 2013

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    While appearing on Sway’s radio show Shade 45 in November 2013, West went on a tirade after the host asked him about his difficulty breaking into the fashion industry. But by the level of their shouting, you’d think the guys were debating international politics. “You ain’t got the answers, Sway!” you can hear West scream. “I’ve been doing this more than you.” Sway slowly but surely calms West down, and the two end the conversation on a more pleasant note. “I ain’t trying to disrespect you, period…I love you man; I’m sorry,” West said. Humble looks good on Yeezus.

Pizza is bae. And yes, I still say bae.
@taylorferber