10 Most DISTURBING Late Night TV Interviews

Megan Fox on “Jimmy Kimmel Live!” (2009)

While promoting her 2009 film “Transformers: Rise of the Fallen,” Megan Fox shared a vulnerable moment with Jimmy Kimmel. She mentioned the first time she worked with “Transformers” director Michael Bay. She was only 15 years old, yet she was dressed in a bikini and 6-inch heels. To make matters more suggestive, she was made to dance under a waterfall. Kimmel showed absolutely no sympathy for her uncomfortable and inappropriate experience. He laughed and wrote off Bay’s behavior as normal. But is it really acceptable to put a child in those conditions?

Ryan Phillippe on “The Tonight Show with Jay Leno” (2008)

Actor Ryan Phillippe’s breakthrough role was the character Billy Douglas on the soap opera “One Life to Live.” Billy broke ground as the first openly gay teenaged character on TV. Keep in mind this role was active from 1992 to 1993, at the height of the AIDS crisis. Fast forward to 2008, when Phillippe promotes his new movie “Stop-Loss” on Jay Leno. The talk show host seemingly couldn’t leave the past behind or get over his own apparent homophobia. He pressured Phillippe to give the camera his “gayest look” and wouldn’t back off despite the actor’s resistance and threats to walk off the set. After being called out by GLAAD, playwright Jeff Whitty, and others, Leno apologized and said it was a dumb joke.

Madonna on “The Late Show with David Letterman” (1994)

This infamous interview was uncomfortable for both Madonna and Letterman. While the guest had nothing in particular to promote, she did have a reason to seek revenge. Letterman had been dragging Madonna in his nightly monologues, and it was time for her to get some payback. She began the interview by asking a salacious question. She dropped the F-word fourteen times. She insulted Letterman’s hair and said he’d lost his edge since becoming successful. The host was visibly unsettled at points. But he wasn’t free of blame either. He repeatedly insisted that Madonna kiss an audience member, despite her repeated refusals. The tense interview ended up being one of the most censored talk show appearances in TV history.

Kanye West on “Jimmy Kimmel Live!” (2018)

Kanye West is one of the most controversial musicians in recent years. From his support for Donald Trump to his antisemitic tendencies, he’s found himself in hot water many times. In 2018, he appeared for an interview on “Jimmy Kimmel Live,” and it didn’t go smoothly. West gave rambling answers to most of Kimmel’s questions. He also compared himself to famous people like Walt Disney, brilliant minds like Leonardo da Vinci, and even religious figures like Jesus. But he was curiously silent on one topic. When asked why he supported Trump, the rapper paused for so long that Kimmel jumped for a commercial break.

Paris Hilton on “The Late Show with David Letterman” (2007)

Paris Hilton was in jail for a brief period in 2007, but that wasn’t the reason for her visit to the Late Show. She was actually on the program to promote her perfume and business ventures. She was assured that Letterman would not bring up her jail time in the interview, but he quickly broke that promise. Not even a minute after she sat down, the host began to grill her on being locked up. Despite Hilton’s visible discomfort and terse answers, Letterman did not let up. Hilton later said in a 2021 podcast episode that she believes he intentionally tried to humiliate her. Letterman later apologized privately and publicly, but his cruel sense of humor certainly left a mark.

Donald Trump on “The Tonight Show Starring Jimmy Fallon” (2016)

Before he was elected president the first time, Donald Trump appeared on “The Tonight Show Starring Jimmy Fallon” in September 2016. Many people expected and wanted Fallon to ask the already-controversial Trump hard questions. However, they got a playful interaction instead. Fallon skirted tough questions and sensitive topics, opting for jokes and games. He also tousled Trump’s hair, which was way too friendly for some viewers. In 2018, Fallon said he would have done the interview differently so as not to normalize the guest’s political beliefs or behavior. Trump of course snapped at the host and told him to “be a man” without regret.

Lindsay Lohan on “The Late Show with David Letterman” (2013)

She intended to promote her new film “Scary Movie 5,” but Letterman decided to grill Lindsay Lohan on rehab and legal troubles. He was egged on by the audience and undeterred by Lohan’s clear discomfort. She took the ribbing with good humor, continuously cracking jokes, but there came a point when it was just too much. She tried avoiding questions. She tried cutting him off. But Letterman kept pestering her about rehab until she began crying. As the interview goes on, Lohan tries to hide her tears until the host hands her a tissue. It’s not in good taste to make your guests cry in the first place, and even worse to draw attention to it.

Abel Ferrara on “Late Night with Conan O'Brien” (1996)

Bad-mouthing guests who’ve been on your talk show is never a good idea. It makes for awkward follow-ups, not to mention it’s just rude. However, Conan O’Brien broke this rule in 2018. He was on Dax Shepherd’s “Armchair Expert” podcast and named the worst guest he ever interviewed: director Abel Ferrara. Ferrara was supposed to promote his 1996 movie “The Funeral,” but he was obviously disinterested in answering any questions. According to O’Brien, Ferrara ran out of the building before they went on air. He was dragged back inside and forced to sit for the segment against his will. Understandably, this added to his bad mood and uncomfortable demeanor.

Jennifer Aniston on “The Late Show with David Letterman” (1998)

The landmark TV show “Friends” was still wildly popular when Jennifer Aniston went on “Letterman.” Early in the interview, he repeatedly asked uncomfortable, objectifying questions about her recent experience in a steam room. Then, with no segue whatsoever, he asks to try something. He puts a lock of Aniston’s hair in his mouth. Despite squeals of discomfort, moving away, and obvious confusion, he continues sucking on her hair. It was clearly a planned bit, considering the musical cues and napkin at the ready, but Aniston was also clearly unaware. Still, the audience laughed and applauded this gross behavior.

Andy Dick & Ivanka Trump on “Jimmy Kimmel Live!” (2007)

Comedian Andy Dick is no stranger to controversy, upsetting humor, and inappropriate conduct. In an unusual appearance on “Jimmy Kimmel Live” in 2007, he sat with businesswoman Ivanka Trump. However, he took this as an invitation to do quite a lot more than sitting. He displayed a complete disregard for personal boundaries when he began stroking Trump’s leg while she was speaking. She tried to diffuse the situation with humor and Kimmel quickly intervened, but that wasn’t enough. He continued touching her legs and hair. Security soon had to show up and drag Dick off the set.

What disturbing moments from late night interviews live rent-free in your head? Let us know in the comments!