25 Celebrities Admit Their Biggest Regrets
It’s easy to imagine that the life of a celebrity is pretty much perfect, because, really, how could it not be? They have a ton of money, they have more resources than almost any “normal” person out there, and they usually are blessed with ridiculously good looks. They also have a team of people to help them make the best decisions possible, so how could anything ever really go that wrong?
As it turns out, all of the money, fame, and good genes in the world can’t prevent you from making mistakes sometimes – and neither can a team of people you pay. Stars, just like the rest of us, have their fair share of regrets, and sometimes they open up in an interview and share those things they wish they had done differently. Sometimes it’s a movie or television role that they wish they never took, sometimes it’s a performance they wouldn’t repeat, and sometimes it’s a haircut they hate looking back on.
These 25 celebrities have admitted their biggest regrets, and they’re definitely relatable:
1. Miley Cyrus
The singer regrets ever making “Wrecking Ball.” Who could forget Miley Cyrus’s iconic music video for her song “Wrecking Ball?” You know, the one where she swung naked on a giant wrecking ball. As it turns out, that’s a move she wish she never made.
During an appearance on the Zach Sang Show, Cyrus was asked to play “Marry, F**k, Kill” with three of her songs, and she wanted to kill “Wrecking Ball.”
She explained, “Swinging around naked on a wrecking ball lives forever. I’m never living that down. I will always be the naked girl on a wrecking ball… My worst nightmare is that being played at my funeral.”
2. Sophie Turner
When it comes to Game of Thrones, Sophie Turner has one big regret: not going to college. Turner first started filming the HBO show when she was 13-years-old, and it didn’t end until she was 23-years-old, so she basically grew up on the show.
She also didn’t have the chance to attend school. During an interview on The Graham Norton Show, she said, “I wish I’d had the university experience.
I wish I could have gone out and drunk a lot and thrown up in the middle of a club without it being photographed! But, I am happy with my Game of Thrones experience. I don’t think I missed out on too much.” She probably didn’t!
3. Whitney Port
The reality star regrets turning down a one night stand with a big celeb.
How’s this for a regret most people don’t have: Whitney Port almost hooked up with Leonardo DiCaprio, but ended up turning down the opportunity.
During an episode of her podcast “With Whit,” she admitted that she had met DiCaprio at a party in Manhattan in 2009.
They exchanged numbers and eventually he asked her if she wanted to come over, and she said no. She explained, “I didn’t want to be with him alone… I was way too nervous to do it and then I lost my chance and it’s really one of my bigger regrets in life.”
4. Kanye West
He wishes there was more nudity in his music video for “Bound 2.” Kanye West has kind of an odd regret that he expressed in an interview with GQ in 2014: he wishes his wife, Kim Kardashian, had more nude scenes in the video.
When talking about the video, he said:
“It was completely morphed and weird and psychedelic and really druggy.”
“I would have just liked to have had more nudity in it. That’s the only thing. I just want to do crazy, colorful sh*t like that that has more nudity,” he added.
5. Kate Winslet
The star regrets her biggest movie role to date. It’s hard to believe that anyone could regret Titanic, considering what a massive success it was, but Kate Winslet does… or at least she regrets her performance in the film.
She once told CNN,
“Every single scene, I’m like ‘Really, really? You did it like that? Oh my God.’
Even my American accent, I can’t listen to it.
It’s awful. Hopefully it’s so much better now. It sounds terribly self indulgent but actors do tend to be very self-critical. I have a hard time watching any of my performances, but watching Titanic I was just like ‘Oh God, I want to do that again.’”
6. Robert Pattinson
He also regrets his biggest movie role so far. Robert Pattinson never really seemed thrilled with Edward Cullen, the character he famously played in Twilight. In an interview with Empire magazine, he explained, “When you read the book, it’s like, ‘Edward Cullen was so beautiful I creamed myself.’ I mean, every line is like that.”
“He’s the most ridiculous person who’s so amazing at everything,” he said.
“I think a lot of actors tried to play that aspect. I just couldn’t do that. And the more I read the script, the more I hated this guy, so that’s how I played him, as a manic-depressive who hates himself,” Pattinson joked.
7. Lamar Odom
The basketball player has one big regret about his marriage to Khloe Kardashian. Lamar Odom was married to Kardashian from 2009 to 2016. In his memoir, Darkness to Light, he revealed that he made one mistake he wishes he didn’t: cheating.
In an interview, he said:
“The chapters about my infidelity, that was the hardest part. I wish I would have treated her the right way.”
“When I see her in these other relationships and everything like that. I always felt she was still my girl.”
8. Jennifer Aniston
The star has a major beauty regret that’s probably pretty surprising. Jennifer Aniston may have been known for her famous haircut from the ’90s, known as “the Rachel,” but she’s never liked it.
In an interview, she revealed how she actually felt about it, saying, “How do I say this? I think it was the ugliest haircut I’ve ever seen.”
When talking about her hairstylist, she said, “I love Chris, and he’s the bane of my existence at the same time because he started that damn Rachel, which was not my best look.”
9. Justin Timberlake
He regrets letting Janet Jackson take all the blame for that infamous Super Bowl halftime show. One of the most iconic moments in pop history is when Jackson and Justin Timberlake did the halftime show, and her boob popped out during their show.
Back then, Timberlake pretty much allowed Jackson to shoulder all of the blame, and her career suffered greatly, while his flourished. Years later, he finally expressed regret about that decision to MTV.
“In my honest opinion now… I could’ve handled it better. I’m part of a community that consider themselves artists. And if there was something I could have done in her defense that was more than I realized then, I would have.”
“But the other half of me was like, ‘Wow. We still haven’t found the weapons of mass destruction and everybody cares about this,'” he reflected. “I probably got 10 percent of the blame, and that says something about society. I think that America’s harsher on women. And I think that America is, you know, unfairly harsh on ethnic people.”
10. Christina Applegate
The actress wishes she took a really popular movie role. Legally Blonde wouldn’t be what it is today if it weren’t for lead Reese Witherspoon.
But before the movie happened, Christina Applegate was offered the lead role of Elle Woods – and turned it down.
She later admitted it in an interview, saying, “The script came along my way and it was right after I had just finished, Married […with Children], and it was a blonde who in that first script didn’t win it but ends up going to Yale, or Harvard, I don’t remember. I got scared of kind of repeating myself.” She added, “What a stupid move that was, right?” Kind of!
11. Courteney Cox
The former Friends star wishes she didn’t get so much plastic surgery. It’s no secret that Courteney Cox has gotten some extensive plastic surgery and facial procedures over the years. Cox has since said she regrets taking things so far.
In an interview with New Beauty, she said:
“You have no idea because it’s gradual, until you go, ‘Oh, sh*t. This doesn’t look right.’ And it’s worse in pictures than in real life.”
When she saw herself in pictures, she was so unhappy with how he looked that she had the procedures reversed.
She said, “I’ve had all my fillers dissolved. I’m as natural as I can be. I feel better because I look like myself. I think that I now look more like the person that I was. I hope I do.”
12. Ben Affleck
He regrets one of his movie roles (and no, it’s not Gigli). Ben Affleck has had his fair share of movie flops, but there’s one he regrets more than all the others: his role in Daredevil.
The movie was a huge critical disaster, and he knows it.
In an interview with Playboy, Affleck said, “The only movie I actually regret is Daredevil. It just kills me. I love that story, that character, and the fact that it got f***ed up the way it did stays with me.”
13. Britney Spears
The pop star wishes her reality show never happened. Remember when Britney Spears and ex-husband Kevin Federline did a weird reality show about their marriage?
Yeah, she wishes she opted out of that.
In an interview with The Telegraph, Spears said, “I would never do something like that again. That was probably the worst thing I’ve done in my career.” Yikes!
14. Viola Davis
If she could take back this major movie role, she would.
In an interview with The New York Times, Viola Davis was asked if she regretted any roles she had passed up. She took the opportunity to speak about her role in The Help, saying, “Almost a better question is, have I ever done roles that I’ve regretted? I have, and The Help is on that list.”
She stressed that it wasn’t because of the other people in the film, explaining:
“I just felt that at the end of the day that it wasn’t the voices of the maids that were heard.”
“I know Aibileen. I know Minny. They’re my grandma. They’re my mom. And I know that if you do a movie where the whole premise is, I want to know what it feels like to work for white people and to bring up children in 1963, I want to hear how you really feel about it. I never heard that in the course of the movie.”
15. Carrie Fisher
This is another actress who regretted an iconic role. Carrie Fisher is maybe best known for her role as Princess Lei in Star Wars, but in an interview, she revealed that she wished she had never taken it.
While most actresses would have done anything to be Princess Leia, Fisher wishes she had passed on the role.
She told The Today Show that if she knew how popular it was going to be, she would have turned it down, saying, “I would never have done it. All I did when I was really famous was wait for it to end.”
16. Jessica Biel
She wishes she never posed nude as a teen. When Jessica Biel was 17-years-old, she did a racy photoshoot with Gear magazine, a move that got her in trouble with her boss, Aaron Spelling, since she played good girl Mary Camden in 7th Heaven.
We imagine this was a very awkward conversation.
Years later, Biel admitted she wished she hadn’t taken the photos, saying, “That photoshoot was a bad decision. I got involved with people who weren’t thinking about me and were instead thinking about what kind of a story they could get out of it. I learned a whole lot from the experience, so it was definitely a blessing in disguise.”
17. Matt Damon
The actor really wishes he wasn’t part of one of his movies. Many people know Matt Damon as Jason Bourne, but as it turns out, he wasn’t a fan of one of the films in the franchise.
It’s kind of hard to believe Matt really said this.
In one interview, he said “It’s the studio’s fault for putting themselves in that position. I don’t blame Tony for taking a boatload of money and handing in what he handed in. It’s just that it was unreadable. This is a career-ender. I mean, I could put this thing up on eBay and it would be game over for that dude. It’s terrible. It’s really embarrassing. He was having a go, basically, and he took his money and left.”
18. Nick Lachey
He’s another singer who regrets his reality TV show. Britney Spears isn’t the only one who regrets taking part in a reality TV show with her significant other.
Basically celebrities, who have legitimate talent, should steer clear of reality TV.
Nick Lachey told David Letterman that Newlyweds: Nick and Jessica was a mistake. He said, “It was among the dumber ideas I think I’ve ever seen executed in history.” He definitely did not mince words!
19. Mary Louise Parker
The actress has talked about how she wishes she didn’t do a nude scene. In one episode of Weeds, Mary Louise Parker appeared naked in a nude scene, but even then she was wishing it wasn’t happening.
You’ve got to trust your gut.
In an interview later on, she said, “I didn’t think I needed to be naked. I fought with the director about it, and now I am bitter. I knew it was going to be on the Internet: ‘Mary Louise shows off her big nipples.’ I wish I hadn’t done that. I was goaded into it.”
20. Katherine Heigl
She got herself in a lot of trouble for talking about her role regrets. Although Knocked Up was a huge hit and a movie that helped catapult her into fame, Katherine Heigl has expressed how much she didn’t like it a few times.
Once, in an interview with Vanity Fair, she said:
“It was a little sexist… It exaggerated the characters, and I had a hard time with it, on some days. I’m playing such a b—h; why is she being such a killjoy?…It was hard for me to love the movie.”
In another interview with The Howard Stern Show, she explained,
“I liked the movie a lot. I just didn’t like me…I really went with it while we were doing it… and afterwards, I was like, ‘Why is that where I went with this? What an a–hole she is!'”
21. Kris Jenner
The reality star and mom-ager wishes she never divorced Robert Kardashian. Here’s a pretty personal regret: in an interview with Daily Mail’s New You magazine, Kris Jenner revealed that her only regret in her life was divorcing her husband, Robert Kardashian.
The famous family could have looked a lot different, if Kris didn’t call it quits.
She said, “The one regret, if I had to do it over, would be divorcing Robert Kardashian. But then there wouldn’t have been Kendall and Kylie, so that’s the way I look at that. I don’t have a lot of regrets.”
22. Mariah Carey
The singer would take back Glitter if she could.
Remember Mariah Carey’s iconic movie Glitter?
Well, she doesn’t think it was so iconic. During an appearance on Watch What Happens Live, she told host Andy Cohen that she hates it so much she doesn’t let anyone discuss it.
The singer, at one point, wouldn’t let people say the film’s name around her.
She said, “It was called the ‘G’ word, we couldn’t bring it up. In retrospect, I’m like, you know what, I learned something, and I’m grateful for that experience. But, it was a horrible couple of years, and then I had to get my momentum back for people to let it go.”
23. Howard Stern
He regrets an interview he did with Robin Williams.
Howard Stern has done a lot of intense interviews, and he doesn’t regret a lot of them – but he does regret one with Williams.
In retrospect, this is so sad.
In an interview, he said, “I loved Robin Williams, but there I am beating him over the head with, like, ‘Hey, I hear you’re f–king your nanny?’ I could have had a great conversation, but I’m playing to the audience. They want to hear outrageousness, and that’s my arrogance thinking that Robin Williams can’t entertain my audience. How stupid am I?”
24. Halle Berry
The actress has no qualms when it comes to expressing her regret for her role in Catwoman. She actually went to The Razzies, an award show for bad movies, to accept her award for “Worst Actress” in person.
This speech was truly unexpected.
In her acceptance speech, she said, “I want to thank Warner Bros. for casting me in this piece of sh*t, god-awful movie. I’d like to thank the rest of the cast. To give a really bad performance like mine, you need to have really bad actors.”
25. George Clooney
The actor regrets starring in Batman & Robin and has called it a “waste of money.” In an interview with Deadline, the Oscar winner thought the big-budget action flick would be his big break.
Clooney told Total Film Magazine:
“My phone rang, and the head of Warner Bros said, ‘Come into my office, you are going to play Batman in a Batman film’ and I said, ‘Yeah!’ I called my friends and they screamed and I screamed and we couldn’t believe it!”
Despite having a production budget of 125 million, the movie only earned 107 million, making it quite the flop.
While reflecting on the project he said, “I just thought the last one had been successful, so I thought I was just going to be in a big successful franchise movie.”