21 Times Celebs Told Reallyyyy Messed Up Stories Like They Were Amusing Anecdotes

1.

Sharon Osbourne once told a story about firing her assistant after a house fire. After they evacuated the burning home, she insisted her assistant return inside to save their dogs and paintings. “He did get the dogs, and the fire engines arrive. Very lovely people. They came, and they had this oxygen for the assistant. So then I said to him, ‘How very dare you, you work here, and you get more paintings out right now.’ I took the mask, and I put it on my dog.”

The next day, Sharon and her husband, Ozzy, were laughing about the incident when the assistant said, “I don’t see what’s funny about any of this. I think I am going to have damaged lungs.” Osbourne said she replied, “‘If you don’t think that’s funny, do you think this is funny?'” then fired him.

2.

After Nikki Reed and Ian Somerhalder got married, Somerhalder joked about how he threw out her birth control so that she would get pregnant. “We decided that we wanted to have children together, and it was just time. But unbeknownst to poor Nikki, she didn’t realize that I was going to go in her purse and take out her birth control,” he said on Dr. Berlin’s Informed Pregnancy Podcast. “By the way, it was the beginning of the pack, so I had to pop all those suckers out. It is a lot of work, especially after a little bit of sangria,” he laughed.

3.

Pedro Pascal found out about what would become his breakout role as Oberyn Martell in Game of Thrones while helping a USC student whom he was mentoring audition for the role. “He’s, like, a 25-year-old kid, really, really talented, good-looking […] He’d never seen the show. I was a huge fan,” Pascal said, noting that he thought the role was “perfect…for me!” While his mentee was in the bathroom, he texted his agent about getting an audition for a part, joking he’d locked his mentee in the bathroom (though this was an obvious embellishment). After his mentee left, Pascal used his mentee’s side to record his audition, then contacted his best friend Sarah Paulson, who was friends with one of the GoT showrunner’s wives, and passed along the tape. Pascal got the part.

4.

Rebel Wilson once told Jimmy Kimmel that she touched Anne Hathaway’s boobs without her consent while filming The Hustle, to the laughter of Jimmy and the audience, then said she’d done something similar to Tom Hardy on the set of This Means War after the director allegedly told her to try and stick her finger in his butt.

5.

Similarly, Margot Robbie said she kissed Brad Pitt in Babylon because she wanted to. She joked, “I thought, ‘When else am I gonna get the chance to kiss Brad Pitt? I’m just gonna go for it.'” She told director Damien Chazelle she wanted to do it and claimed that Damien replied, “‘Wait, hold on. You just wanna kiss Brad Pitt.’ And I was like, ‘Oh, so sue me. This opportunity might never come up again.'”

6.

Another super creepy “humorous” story is Jason Segel talking about writing the role of Violet in The Five-Year Engagement, his character’s love interest, for Emily Blunt. In 2012, Segel joked of writing the sex scenes, “There is some advantage to writing the stuff. I wrote all these love scenes with Emily Blunt, and she shows up, and she just has to do it because we’re paying her money, and it’s her job.”

7.

Lena Dunham’s weird rant about Odell Beckham Jr. not speaking to her at the Met Gala is still so cringeworthy to me. “It was so amazing because it was like he looked at me, and he determined I was not the shape of a woman by his standards,” she said in an interview with Amy Schumer. “He was like, ‘That’s a marshmallow. That’s a child. That’s a dog.’ It wasn’t mean — he just seemed confused. The vibe was very much like, ‘Do I want to f— it? Is it wearing a… Yep, it’s wearing a tuxedo. I’m going to go back to my cellphone.’ It was like we were forced to be together, and he literally was scrolling Instagram rather than have to look at a woman in a bow tie. I was like, ‘This should be called the Metropolitan Museum of Getting Rejected by Athletes,'” Dunham joked.

8.

At a show in Las Vegas after hosting the Oscars, Amy Schumer revealed a joke that she’d been “banned” from telling during the ceremony about the fatal shooting of Halyna Hutchins on the set of Rust. The joke was, “Don’t Look Up is the name of a movie? More like don’t look down the barrel of Alec Baldwin’s shotgun.” I’m still scratching my head on why Schumer thought A) this was an appropriate joke and B) that she should tell the story of her not being allowed to tell it.

9.

Chelsea Handler has made several racist comments about Angelina Jolie’s children over the years, especially in regards to Maddox, who Jolie adopted from Cambodia. In her book Are You There, Vodka? It’s Me, Chelsea, she told the story, “I rolled over and picked an Us Weekly magazine off the floor. The cover had a picture of Angelina, Brad, and their little Eskimo son, Maddox. I sat staring at the photo, wondering why this little guy looks so pissed off in every picture. At first, I thought he was just pissed about his mohawk, but then I realized he’s probably furious.”

“Maddox must have thought he hit the jackpot when some A-list celebrity rescued him from third-world Cambodia, only to discover that she was going to shuffle him back and forth to every other third-world country in the universe. He’s probably like, ‘When the fuck are we gonna get to Malibu, bitch?'” The joke only served to make Handler look racist.

10.

Thomas Middleditch has told some questionable stories about his experience “swinging” with his wife. He once joked to Playboy magazine, “I self-deprecatingly call myself a pervert, but that’s not what it is. I just like it. I’m sexual” after revealing that he didn’t tell his wife that he wanted to be polyamorous until after they were married, at which point, as he describes it, he casually said, “Mollie, I’m sorry, but we have to get nontraditional here.”

11.

Bill Cosby has a history of telling stories and jokes about Spanish Fly (an alleged aphrodisiac) — including in this interview with Larry King. This is one of those messed-up celeb stories that took years for people to realize how messed up it is, but in the context of the allegations against Cosby, it’s far more disturbing.

12.

Many “humorous” stories from the set of That ’70s Show have also been viewed in a new light in the wake of Danny Masterson’s rape conviction. In particular, in one interview, Ashton Kutcher talked about a bet he made with Masterson where Masterson would pay Kutcher $20 if he used his tongue in a kissing scene with then-14-year-old Mila Kunis. He then said she was “receptive” (Kunis denied he had used tongue, saying she blocked him, but Kutcher maintained that he had) and clarified she was “15 by then,” adding, “There’s a big difference, that one year makes the whole world change.”

13.

John Stamos once told a super creepy story about getting his friend laid by tricking a woman into thinking she was having sex with him in the mid-’80s. “I was in a band. I was playing somewhere in Finland, and there was a girl hanging around who was really drunk and interested in me. I wasn’t into her, but my friend was. So the girl came back to my hotel, and I turned the lights down, and we started making out. I said, ‘Hold on a second, I’ve gotta go brush my teeth.’ It was dark, I left the room, and I sent in my friend who looked like me. And she thought she was having sex with me, but she was really having sex with my friend.”

14.

Jennifer Lawrence once told a “funny” story on The Graham Norton Show about scratching her butt on sacred Hawaiian rocks while filming The Hunger Games. “We were filming in Hawaii, and there were…sacred…rocks — I dunno, they were ancestors, who knows — they were sacred. And you’re not supposed to sit on them because you’re not supposed to expose your genitalia to them. I, however, was in a wet suit for this whole shoot, so, oh my God, they were so good for butt itching!”

She says one of the rocks she used for itching was dislodged and fell down the side of a mountain, coming close to striking and killing the sound engineer. “All the Hawaiians were like, ‘Oh my God, it’s the curse!’ And I was sitting in the corner like, ‘Haha! I’m your curse! I wedged it loose with my ass!'” She later apologized for her comments, saying she meant “absolutely no disrespect to the Hawaiian people.”

15.

I just feel icky watching this Jimmy Kimmel interview with Brett Ratner, where he tries to prove what a funny, practical joker Michael Jackson was by telling a story about how he accompanied Michael to throw water balloons at a man experiencing homelessness.

16.

In another “prank” story, Demi Lovato once tweeted about a trick she pulled on her bodyguard, claiming she’d hired a sex worker to grab “him in his ‘area.'” She then deleted it, then tweeted, “I could tweet something about craving jelly beans and it would offend someone,” and told people to listen to her song “Warrior,” writing, “Of all people I know about sexual abuse. You don’t have to educate me.” Lovato eventually apologized for her tweet, and her bodyguard Max called the incident Lovato referred to “a joke and a fun prank,” saying he wasn’t offended.

17.

On one episode of The Adam Friedland Show (later removed from Spotify), Friedland and Matty Healy told a pretty disturbing story about leaving Healy’s apartment with friends. One of the women with them went back to Healy’s apartment because she’d forgotten her water bottle, only to apparently find “Matty, like, on his phone and then on his 77-inch OLEDs just got Ghetto Gaggers blaring,” according to Adam, referring to a racist and misogynistic porn site where Black women in particular are degraded and humiliated. “Thirty seconds after the hang, just hardcore pornography.”

Healy corroborated the story, saying, “You’re not exaggerating. It was 30 seconds, like, you guys were still waiting outside. She came back in; I was already flustered. I was dressed as ‘guy who is jacking off,’ so I had, like, an untucked shirt, and I think it literally was Ghetto Gaggers on the TV — somebody just getting, like, brutalized,” Healy joked.

18.

In an anthology about bad sex, Alison Brie wrote about convincing a male gay friend to have sex with her. “And what if he were to discover he was actually straight? I would have saved him from a life of dysfunctional penetration. Literally my vagina would have been his road to salvation!” she wrote. The two did have sex, even though he purportedly didn’t want her to touch his penis, and had difficulty getting aroused, which only caused Brie to brainstorm new solutions. Brie called the whole thing a failure, though she’s apparently still friends with the man.

20.

This one also isn’t a “humorous” story, but I still think it’s so ridiculous that Matt Damon framed having only recently “retired” the f-slur as if it was a good thing. In an interview, he claimed that after he made a joke using the slur, his daughter gave him a “treatise” on the subject. “The word that my daughter calls the ‘f-slur for a homosexual’ was commonly used when I was a kid, with a different application,” Damon said. After making the joke, “She left the table. I said, ‘Come on, that’s a joke! I say it in the movie Stuck on You!'”

He later walked back this version of the story, saying he had “never called anyone ‘f****t’ in [his] personal life and this conversation with [his] daughter was not a personal awakening.” He said he was attempting to contextualize to his daughter the progress that had been made since he was a kid, telling her he’d heard the F-slur often as a kid “before [he] knew what it even referred to.” He said he “explained that that word was used constantly and casually and was even a line of dialogue in a movie of mine as recently as 2003; she in turn expressed incredulity that there could ever have been a time where that word was used unthinkingly.”

21.

And finally, on a podcast episode in 2019, T.I. stated that he takes his daughter to the gynecologist yearly to check if she’s still a virgin. (For the record, checking if the hymen is intact is not a good indicator of virginity, and the World Health Organization has called virginity testing “a violation of the human rights of girls and women”). T.I. later claimed he’d “embellished” and “exaggerated” the story, that he’d only gone to her doctor’s appointments when she was younger, and that his daughter had no problem with it (though she did, he said, “have a problem with me talking about it,” which he claimed to have apologized for).

“She understands my intentions, and she knows who I am, who I’ve always been,” he continued, but his daughter Deyjah’s comments indicated otherwise. She claimed T.I. had come with her to her gynecologist since she was 14 or 15 and that she “couldn’t have said no.” She called the situation “a little traumatizing,” saying she was “very shocked, hurt, angry, [and] embarrassed” that T.I. had spoken publicly about it.