Celebrity Interviews That Definitely Crossed The Line

There’s a lot that goes into a good celebrity interview. Whatever we read or see on screen has likely been founded on years of hard work. For journalists, that includes extensive education and work experience; for celebrities, there’s media training and the hawk-like eye of a powerhouse publicist. Unfortunately, it’s all too easy to miss the mark — and if there’s one thing the tabloids are good at, it’s immortalizing cringey interviews.

The internet has a way of finding the worst thing someone has ever said and bringing it back into the spotlight — whether it’s a rare misstep from Barbara Walters, Howard Stern just being Howard Stern, or John Mayer having an unhinged, stream-of-consciousness conversation with a Playboy journalist. These celebrity interviews completely crossed the line, but if they prove anything, it’s the power of words. An offhand remark can have a lasting impact, and at the end of the day, at least the publicists of the world are getting some work.

David Letterman's 2013 interview with Lindsay Lohan aged like warm milk

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In recent years, the press has — at least partially — evolved in the way it treats celebrities who are struggling with addiction and mental health disorders. That didn’t seem to be the case for David Letterman in 2013, though. His “Late Show” interview with Lindsay Lohan was so uncomfortable that it went viral eight years after the fact. As one Twitter user put it, “This clip is horrifying in so many ways.”

Lohan appeared “Late Night with David Letterman” to promote her flick “Scary Movie 5,” but his questions were mainly focused on her struggle with addiction, her past shoplifting conviction, and her upcoming stint in court-ordered rehab. Though Lohan tried to politely shut it down the aggressive questions about her addiction issues and legal problems, Letterman hit the point of no return when he pulled out a list of things the actress supposedly “endured,” which — rightly — caused Lohan to raise her voice. “I’ve gone through a lot in life, and I’m looking forward to actually just taking time for me,” she asserted as he continued to read his list. “You can’t make a joke of it. That’s so mean. No, you’re not doing that! We’re not doing that.” At one point, Lohan was almost in tears.

Apparently, Barbara Walters' most interesting people also 'don't have any talent'

The Kardashian-Jenner clan rivals Fortune 500 CEOs when it comes to business, as the family managed to parlay an unfortunate sex tape leak into a billion dollar enterprise. Sure, critics laughed when Forbes named Kylie Jenner the youngest self-made billionaire (especially since there’s some debate about the true size of her wealth). Nonetheless, the Kardashians are startup sharks, launching one successful business after another — from Kim Kardashian’s Skims, which The New York Times estimates is valued at $1.6 billion, to Khloé Kardashian’s denim line, which made $1 million in sales on day one. So, why was Barbara Walters so salty?

In 2011, the Kardashians made Walters’ list of most fascinating people, but the interview read more like a hostile takedown than a celebration. At the start, she acknowledged their reality TV empire, describing it as “a strange mix of trashy sex, upscale excess, tabloid melodrama, and suburban family life.” This isn’t inaccurate, but things crossed the line when Walters described the family as talentless. “You don’t really act. You don’t sing. You don’t dance. You don’t have any — forgive me — any talent,” she declared.

Though the sisters agreed they don’t have traditional talents as performers, Kim immediately put Walters in her place. “I think it’s more of a challenge for you to go on a reality show and get people to fall in love with you for being you,” she clapped back. Have some respect.

Ricky Martin felt 'violated' by Barbara Walters in 2000

Taylor Swift has a long-standing relationship with Ellen DeGeneres, which made it all the more unfortunate that the talk show host wouldn’t drop her clearly misguided bit. Anyone with an internet connection knows that Swift’s early career was largely scrutinized because of her highly public love life. It was a sore spot, a bruise that was continuously pressed on — and DeGeneres turned it into a joke.

During the Grammy winner’s 2012 appearance on “The Ellen DeGeneres Show,” the talk show host pressed the songwriter about the subject of her single “We Are Never Ever Getting Back Together.” She turned it into a game: DeGeneres would show Swift pictures of people the song might be about, and Swift would ring the bell if it was true. However, the issue was that the singer was clearly uncomfortable. “I don’t know if I’m going to do this,” Swift confessed. “This is the one thing that I have. It’s like the one shred of dignity that I have.”

DeGeneres did not heed Swift’s warning and pushed until the singer was nearly in tears. “I don’t want to. I don’t want to,” she lamented, with her voice clearly shaking. “Because they’ll send me angry emails, and I don’t want to get them.” DeGeneres ended up taking the bell and ringing it herself until Swift cried, “Stop it, stop it, stop!” With DeGeneres’ recent controversy, this old interview looks like a canary in a coal mine.

Humiliating Jessica Simpson may be the least bad thing about John Mayer's Playboy interview

In the past, it seems like John Mayer may have treated his relationships with a sort of fragrance that eventually caught up to him. 2010 was arguably a terrible year for the singer-songwriter; that’s when Taylor Swift’s “Dear John” publicly eviscerated him. Mayer later told Rolling Stone that the track “humiliated [him] at a time when [he’d] already been dressed down.” In truth, Mayer didn’t exactly help himself.

Swift never officially confirmed who “Dear John” was about, and Mayer should’ve probably taken a page from her book. Prior to the release of the track, the “Gravity” singer dug himself into a potentially career-ruining hole by forgetting to bring a muzzle to an interview with Playboy. In the now-infamous interview, Mayer made a string of disappointing racially-charged statements, including using the n-word and claiming that his “d**k is sort of like a white supremacist” because he doesn’t generally hook up with Black women. He also used a homophobic slur and publicly embarrassed Jessica Simpson by calling her “sexual napalm,” just to round things out.

Obviously, this enraged everybody from Simpson to Mayer’s fans to pretty much anyone who read the interview or heard about it. An apology tour later, and it looks like Mayer has been let back into Hollywood, but he’s still known as the dude who wanted to desperately prove he’s “not like every guy” by acting worse than every other guy.

The Chainsmokers clearly haven't learned when to quit

The Chainsmokers probably could’ve co-headlined John Mayer’s apology tour. When the pop duo, consisting of members Alex Pall and Andrew Taggart, landed a 2016 Billboard cover story, they basically looked at what he told Playboy and said hold my beer — quite literally. They even bragged, “We’re way too good at drinking,” which has a certain level of irony considering it seems like taking shots of vodka while talking to a journalist was their first mistake.

Off the bat, the interview (aptly titled “The Bros of Summer”) devolved into a penis-measuring contest as Pall admitted the duo’s genitalia stood at “17.34 combined inches” from “tip to tip” — and that’s not even the worst part. Rather, that award goes to Pall’s general views about women. “Even before success, p**sy was number one,” he admitted. “Like, ‘Why am I trying to make all this money?’ I wanted to hook up with hotter girls. I had to date a model.”

As much as the interview crossed the line, it actually had little impact on the duo’s overwhelming success. If anything, it was proof that we manifest our truth. Pall succeeded in his quest to date models. According to his ex-girlfriend Tori Woodward, who posted incriminating Instagram stories that were captured by People, the Chainsmoker — at the very least — cheated on her with a “lame Instagram model,” effectively ending their relationship. A model is a model, right?

It's impossible to unhear Howard Stern asking Baby Spice when she 'developed'

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Another day, another inappropriate Howard Stern interview. The radio host built a media empire on the foundation of his salacious, overly crude interviews. Each one seems more polarizing than the last — from the regretful interview where he called out Robin Williams to that time Donald Trump agreed that his own daughter was “a piece of a**.” Still, Stern’s interview with ’90s icon Emma Bunton possesses a unique level of horror. It’s one thing when Stern rudely glosses over tabloid gossip, but it’s another when the entire basis of an interview is his own sexist ideation.

In 2005, Bunton (aka Baby Spice of The Spice Girls) stopped by Stern’s studio to presumably discuss “Free Me,” the album she dropped a year prior. Instead, Stern almost immediately came in hot with questions regarding her underwear, body, and sexuality. Not only did he ask her when she lost her virginity, he also waxed poetic about all the ways he imagined her in the bedroom. “You’ve got a hot little body,” he oozed. “I can see you like girl-on-girl action, I could see you with two guys. I could see you doing a lot of things. Milkman’s daughter, 14 years old.”

It’s hard to tell what’s worse: Stern claiming Bunton wanted attention for her body or asking her, “What age did you develop? 14? When did you get your period? How old were you?” Gross.

Jimmy Kimmel's 2013 interview with Megan Fox took a creepy turn

In recent years, Ben Affleck has been open about his struggle with alcohol. His 2020 New York Times profile was the first time he extensively spoke about his path to sobriety, but some of his hiccups have ended up as tabloid fodder. One of those was allegedly not this completely unhinged 2004 interview with the Canadian TV series “Box-Office.” Was Affleck or journalist Anne-Marie Loisque the one who crossed the line? Is there a world where it was both?

During the interview, Affleck appeared drunk and got handsy with Loisque, pulling her onto his lap and whispering into her ear in a fake French accent. He then asked her why she wasn’t showing more cleavage. She said that it’s “Sunday morning,” and he said, “That’s never stopped you before from getting those t***ties out.”

Loisque was giggling throughout the whole interview. Once the press coverage went south, she defended the actor’s actions, claiming that it was taken out of context; the whole thing was apparently an act for her show. “When the cameras rolled, we would start to do that game,” she told The Hollywood Reporter. “As soon as it stopped rolling, there was none of that.” Okay, but it’s still hard to watch.

Giuliana Rancic's 2013 interview with Aziz Ansari could've won a Golden Globe for it's cringe factor

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After the whole “patchouli oil and weed” incident that nearly ruined Giuliana Rancic’s career, it’s clear that the TV host is — in the infamous words of Jennifer Aniston to Brad Pit — missing a sensitivity chip. When her 2013 Golden Globes interview with Aziz Ansari resurfaced in the tabloids, it didn’t exactly help her plight.

According to Radar, Rancic interviewed Ansari as part of her typical awards show red carpet coverage. But rather than focus on the actor’s work with “Parks and Recreation,” the TV personality randomly assumed — with no basis — that he had “good rhythm,” prompting Ansari to ask her if that was because of his “chocolate skin tone.” Rancic claimed, “No, not based on your very beautiful tone,” and Ansari schooled her on “the stereotype” that “Indian men know how to dance.” When she wouldn’t stop pressing, the actor decided to perform a dance that he called “What? That’s racist … don’t say that again.” To make things more awkward, Rancic proceeded to do the dance and repeat the phrase.

To the probable delight of Rancic, the Ansari interview has virtually been scrubbed from the internet, but unfortunately, the tabloids never forget.

Sean Connery's 1965 interview with Playboy didn't just cross the line – it kept going

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Some things get better with age, but one of those things is not Sean Connery’s controversial 1965 Playboy interview. The horrific interview — in which he promotes domestic violence — resurfaced after the star’s death in 2020. What’s worse is that he seemingly clung to his misguided ideals for decades.

In the interview (via People), Connery claimed that he didn’t think there was “anything particularly wrong about hitting a woman,” though he didn’t “recommend doing it in the same way that you’d hit a man.” Instead, the actor suggested an “openhanded slap” could be “justified” as long as “all other alternatives fail and there has been plenty of warning.” Connery even admitted that he would hit a woman if she was “a b***h, or hysterical, or bloody-minded continually.”

In 1987, Barbara Walters gave Connery a chance to walk back on his comments. Instead, he admitted, “I haven’t changed my opinion.” In 1993, Vanity Fair gave him another try, and he maintained that some women seek out “the ultimate confrontation — they want a smack,” which isn’t the worst thing you could do. Change did not come until 2006, the same year his first wife accused him of physical and mental abuse, according to People. That year, he told The Times that he didn’t think “any level of abuse against women is ever justified.” Nonetheless, the original interview is part of his legacy.

Jesse Eisenberg probably shouldn't have said anything during his 2013 'Say My Name' interview

David Letterman is known for crossing the line. While he’s not quite Howard Stern, the late night host does have a knack for pushing buttons, particularly with women who appear on his show. This includes Janet Jackson, who clearly didn’t appreciate being prodded about her Super Bowl scandal, and Jessica Alba, who awkwardly had to field questions about her “tiny, little outfit” on the set of “Honey.” That’s all the more reason why Drew Barrymore’s wild 1995 interview is a delight — even though it completely crossed the line. The actor, who was firmly in her wild child phase, completely flipped the script.

The scandalous moment occurred right at the start. The star gave Letterman a bouquet of flowers for his birthday — but that wasn’t his only present. Right after Barrymore sat down, she got right back up, climbed on the talk show host’s desk, did a sexy dance, pulled up her shirt, and flashed him. This was an instant headline grabber and her most memorable talk show moment to date. Years later, Barrymore still has no regrets. In 2018, she told Stephen Colbert, “I’m such a different person now that it doesn’t feel like me, but I’m still into it.”

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