Watch the 6 Most Awkward Celebrity Interviews Ever

The celebrity interview sounds like a good idea in theory — who doesn’t want to see their favorite stars palling around with talk show hosts, providing insight into their personalities and their work? In reality, however, many celebrity interviews become painfully awkward encounters that only serve to make the stars being interviewed look foolish or, worse, downright cruel. There are many awkward celebrity interviews out there, floating around on YouTube, but we’ve gathered together six of the most painful of them all. Enjoy, if you dare.

1. Paris Hilton on the Late Show with David Letterman

Now that we’ve all thankfully forgotten about Paris Hilton, we can comfortably revisit her past and laugh. This appearance of hers on The Late Show with David Letterman is certainly as hilarious as it is awkward, as the irreverent Letterman takes perverse glee in undercutting the perfume Hilton is promoting to instead grill her on her recent time spent in jail. “This could be your legacy,” he says about her time in jail, as she struggles to keep the fake smile plastered to her face and force him to move on. Classic.

2. Courtney Love interrupts Madonna after the MTV VMAs

In the wake of MTV’s 1995 Video Music Awards, interviewer Kurt Loder was interrupted mid-question by a projectile makeup kit. The kit turned out to belong to Courtney Love, best known for being the drugged-up girlfriend of Kurt Cobain, who Loder mistakenly invited up to the platform to speak with them. Love was characteristically obnoxious and almost certainly on something, so Madonna could do little else but look on in thinly veiled disgust until she finally excused herself. The interview ends with Love literally faceplanting out of nowhere.

3. Lark Vorhees on Entertainment Tonight

Former Saved by the Bell star Lark Vorhees was well on her way down the ladder of fame when she appeared on a segment of Entertainment Tonight. Given the chance to refute rumors circulating about her mental health in an interview with ET‘s Christina McLarty, Vorhees did anything but dispel the rumors. Within less than a minute, she spouted an amazing amount of nonsensical statements based on faulty vocabulary. It looks as though she’s on the verge of a breakdown with each word she can barely manage to say. It feels bad to laugh, but her word salad is just too ridiculous to take seriously.

4. Billy Bob Thornton on Q TV

When he isn’t starring in acclaimed movies and television series, actor Billy Bob Thornton spends his time fronting the country pop band The Boxmasters. While promoting the group’s latest album on Canada’s Q TV, Thornton sat down for an agonizing 13-minute interview. With the host’s very mention of his film career, Thornton immediately shut him out and suggested he was belittling his music as a hobby by referring to his more well-known onscreen accomplishments. The host continues to press Thornton for the duration of the painful interview, as he refuses to get past the chip on his shoulder and actually answer any questions without his bitter attitude.

5. Michael Jackson with Martin Bashir

Pop star Michael Jackson endured plenty of controversy in his late life before his untimely death in 2009, and much of that started with the full-length documentary Living with Michael Jackson — particularly his interview segment with British TV personality Martin Bashir. Jackson discusses the abuse he endured as a child star before going into even more disturbing territory, mentioning that he’s slept in the same bed with many young boys and then struggling to backpedal on the comment, to make Bashir and the viewing audience understand that he’s speaking about love. Given the sexual abuse allegations that plagued him in those years, this interview is perhaps more disturbing than it is awkward.

6. Tom Cruise on The Oprah Winfrey Show

You’ve almost certainly seen this one. While doing press for his upcoming film War of the Worlds, Tom Cruise made an infamous appearance on the Oprah Winfrey Show, opening up about his new-found relationship with actress Katie Holmes. Perhaps in response to the crowd’s encouragement, Cruise became ridiculously excited and went so far as to jump on Oprah’s couch as he repeatedly declared his love for Holmes. Cruise has always been an enigmatic and uncomfortably intense public figure, but his offputting intensity rose to new heights with this appearance, which remains painful to watch even 10 years later.

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