These 40 Celebrities Opened Up About Their Greatest Regrets

Regrets. We’ve had a few. Or perhaps you’re a person who has a whole host of them? Maybe you are wishing you took that job, are reminiscing about a lost relationship, or are groaning whenever you see your yearbook photo. If so, then believe it or not, you’re much like these 40 celebrities. They’ve spilled the beans on their greatest regrets – from lost loves to incredibly embarrassing hairdos and awkward tattoos. Read on, and you’ll discover what decisions Kate Winslet and Jennifer Aniston are still mortified about many years later.

40. Melissa missed out on Ryan romance

Before he was headlining big-time blockbusters, there was a time in the mid 90’s when Ryan Reynolds was just a young upstart trying to make it in Hollywood. And the Deadpool star appeared in the 1996 TV movie Sabrina the Teenage Witch that went on to birth the popular series. Alongside him was Melissa Joan Hart, and the pair had a brief romance. However, it didn’t go on long, with Hart telling Studio 10 in Australia, that despite them being “smitten and cute” she ultimately decided to stick with her boyfriend. Oh, Melissa!

39. Sophie should’ve slummed it as a student

Game of Thrones shot a young Sophie Turner to international fame, and that HBO glory ultimately helped her bag a Jonas brother. But the English actress still has a major regret about working on the show from the age of 13 until she was 24. Turner revealed all on The Graham Norton Show. Spilling the beans, she told Norton, “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!” Erm, sure Sophie.

38. Haircut own goal by David Beckham

Throughout his long career, soccer ace David Beckham displayed a wide array of different — and sometimes terrible — haircuts. Taking risks is part of being a sports-fashion icon. But there’s one style in particular that the Englishman regrets having. The cornrows. During a candid appearance on The Graham Norton Show, he opened up, “[They] were maybe a bad decision! It was bad timing as well because I was going to South Africa at the time with England and ended up meeting Nelson Mandela, so that’s why I regret that.” So you should, David.

37. Overthinking Oprah

With a reported $2.9 billion in the bank, it’s fair to say Oprah Winfrey has done pretty well for herself. But the talk show guru is still just like all of us, in that she has a few regrets about her past. Yes, Winfrey admitted to her own channel and magazine that her main one was wasting time worrying about things that ultimately didn't matter that much. Whatever you say, Oprah. Compared to the average joe, it seems like you did a pretty impressive juggling act throughout your unparalleled career. We are sure that Stedman is proud of you!

36. Benson’s bleaching blues

From the outside, Ashley Benson appears to have everything: talent, good looks, and considerable fame and fortune. But the star has regrets too, and one in particular centers around a bleaching fiasco that was immortalized during one of her biggest roles. The actress told People, “My biggest hair regret was when I tried to bleach my hair and then the person who did, bleached my whole head off and I lost all my hair. You can see it in season three of Pretty Little Liars. I have horrible hair.” Well, the show's stylists did their best with it!

35. Courteney corrected cosmetic blunders

One of Courteney Cox’s main regrets is having too much cosmetic surgery. The actress told New Beauty magazine of her regret, stating, “You have no idea because it’s gradual… And it’s worse in pictures than in real life.” So the Friends star shelled out to undo all the work she had done. Cox continued to New Beauty, “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.”

34. Garner’s guilt over early wedding

Jennifer Garner has a very specific regret: marrying too young. The Alias star was only in her 20s when she tied the knot with Scott Foley back in 2000. It soon became apparent that the two had bitten off more than they could chew in terms of their big commitment. She told Allure, “We were full-on grown-ups, but looking back I’m aware we did not know what hit us. We didn’t have a shot. He’s a really good guy, and we just imploded.” Garner also revealed that she found divorce a “crushing experience.” Ah, bless.

33. Who are you to complain, Pete

The Who’s place in rock ‘n’ roll history is well assured. But if the band’s guitarist and chief songwriter Pete Townshend could have his time again, he wouldn’t have joined them. It seems like solo work is what he's enjoyed most. He told Uncut magazine, “What would I have done differently? I would never have joined a band. Even though I am quite a good gang member and a good trooper on the road, I am bad at creative collaboration.” Yes, the windmilling guitar god wishes he went solo, claiming he “would be less physically damaged today.”

32. Megan outfoxed by Marilyn tattoo

You may remember seeing a large tattoo of the iconic Marilyn Monroe on actress Megan Fox’s arm. It seems like a pretty classy piece of ink, but the Transformers actress regretted getting it and had it removed. She told Italian fashion magazine Amica why. Fox said, “She was a negative person… Disturbed, bipolar. I do not want to attract this kind of negative energy in my life.” That is fair, as Monroe's legacy is much more complicated than most people realize. Fox didn't want to follow that same path in her own life, which is fair.

31. The News is Huey regrets not selling out

Huey Lewis sold quite a lot of records in his heyday. But the News frontman regrets not selling out and making a ton more cash. In an appearance on Jimmy Kimmel Live, Lewis told the host that he and his band flew to Atlanta in the wake of Michael Jackson's $50 million Pepsi deal to discuss a similar tie-in with Coke. He said, “[Coke] offered us millions of dollars [to use] “The Heart of Rock & Roll” in a commercial. I said no.” The crooner later described that decision as “stupid.”

30. The Reality is, Britney regrets THAT show

Remember back in the noughties when Britney Spears and Kevin Federline were a big item? Well, during that time the couple made a reality show called Britney and Kevin: Chaotic. And it was really bad, even by the low standards of reality television. In an interview with British newspaper The Telegraph, the “Toxic” songstress admitted as much, expressing her deep regret about the cringeworthy series. She said, “I would never do something like that again. That was probably the worst thing I’ve done in my career.” At least that is all in the past!

29. Ellie apologetic about accent

Ellie Goulding has enjoyed a successful singing career thus far; there's no denying that fact. But the British pop star has a strange regret: learning to talk “posh” in order to conceal her working-class background. Indeed, Goulding told The Observer, “I became fixated on speaking well. I felt like people just knew I was from a council house and that I was poor because of the way I spoke. I feel silly because I’m not ashamed of the Hereford accent now and it’s too late to get it back.” Hopefully, she now feels more comfortable in her own skin.

28. Kim K didn’t nail her engagement look

Kim Kardashian is famous for — ahem — not a lot really. Being a celebrity is her biggest claim to fame, but the socialite and businesswoman revealed on Patrick Starr’s YouTube channel a major regret. She said, “One of my biggest photo regrets is when I got engaged [to Kanye West] and I had the shortest nails when I showed my picture. It would have looked so much better with long nails.” Oh the horror, Kim! We wonder if that broken relationship has produced any other regrets in the time since that interview.

27. Fame no walk in the park for poor George

He’s one of the world’s richest actors, he has won Oscars, and he has dated some of the world’s most beautiful women. But George Clooney rather regrets his fame and success, when all is said and done. The movie star told Esquire in 2014, “The truth is, the big house on a hill is isolating. There’s no other way to say it. There are restrictions to this kind of fame. I haven’t walked in Central Park for 15 years. I’d like to, you know?” Erm, we’ll happily swap places with you George?

26. Jennifer jaded by popular hairstyle

Remember “the Rachel?” The haircut that millions of women seemed to suddenly want in the mid-1990s due to it being sported by Rachel Green on Friends? Well, the actress who played Rachel, Jennifer Aniston, has admitted her regrets over the iconic hairdo. She told the The Telegraph, “How do I say this? I think it was the ugliest haircut I’ve ever seen. I love [hair stylist] 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.” Well, that style certainly didn't hurt Aniston's career!

25. Idle Ozzy should have learned to play

Ozzy Osbourne is a guy who — unsurprisingly — has a few regrets. The wild frontman of Black Sabbath has expressed remorse at cheating on his wife Sharon, as well as exposing the family on a reality TV show. But there’s another more innocent one: not learning an instrument. Osbourne told Rolling Stone, “That’s one of my biggest regrets. I can play a little bit of harmonica, and that’s about it. But I have an ear for melody.” Good thing he has the pipes and stage presence to make up for his lack of technical skills.

24. Bieber makes taxing apology

Pop idol Justin Bieber has made a lot of mistakes whilst growing up in the public eye. That much is to be expected. But the Canadian was left red-faced with regret after a dig at the equally turbulent celeb Lindsay Lohan. You see, Bieber didn’t like the comparison between his unruly lifestyle and Lohan’s, and made a jibe at her 2012 tax returns to make his point. But the singer eventually removed his post and wrote: “I realized right away that what I said at the end was wrong.” Kudos to Bieber for owning up to his mistake.

23. Silly Sheen seriously sorry

Another man whose unruly behavior means he should have more than a few regrets in life is Charlie Sheen. But the wayward, former Two and a Half Men star did apologize for one particular indiscretion. He had labeled his former co-star Jon Cryer as a “traitor” after he didn’t contact him when Sheen departed the sitcom. But Sheen later told Playboy, “That was wrong. I whaled on him unnecessarily.” The troubled actor then tacked on, “He’s a beautiful man and I miss him.” Perhaps the two men managed to patch up their relationship since the show ended?

22. A Titanic regret for Ms. Winslet

You might think Kate Winslet would be proud of her performance in 1997’s Titanic. But the English rose hates her part in the movie. She remarked, “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.’” Well, we thought you were great, Kate!

21. Broken-hearted Burt

Here’s one that will surely bring a tear to your eye. And it comes from the late Hollywood legend Burt Reynolds. Yes, back in November 2015, the Deliverance star told Vanity Fair of his regret at losing the love of his life, actress Sally Field. Reynolds said then of the woman he dated for almost five years, “I miss her terribly. “Even now, it’s hard on me. I don’t know why I was so stupid. Men are like that, you know. You find the perfect person, and then you do everything you can to screw it up.”

20. Crosby’s compunction

David Crosby was a key player in both The Byrds and Crosby, Stills & Nash. That career arc is pretty hard to complain about, but in the 2019 documentary Remember My Name, the roots rocker told director Cameron Crowe how he sincerely regretted his boorish behavior towards others during those times. He lamented, “All the guys that I made music with won't even talk to me. One of them hating my guts might be an accident. [I did things that were] just awful.” It seems all the fame and money in the world can't repair some broken relationships.

19. Kerry’s crying shame

Actress Kerry Cahill revealed a heartbreaking remorse to HuffPost in 2017. The Walking Dead star said, “I regret that I didn’t ask my dad for more dating advice. I was 27 when he died [in the 2009 mass shooting at Fort Hood, Texas]. I hadn’t really focused on relationships much. I missed a lot of good nuggets of wisdom from my dad, who obviously understood men better than I do. There’s something about having your dad’s voice in the back of your head that can give you the confidence to walk away,” she added. How sad.

18. Wendy promises to button her lip next time

Wendy Williams is no stranger to controversy. But the chat show host knew she had gone too far when she mimicked a cleft lip upon speaking about Joaquin Phoenix, whom she found “oddly attractive.” After complaints from the likes of Cher and football star Adam Bighill — who has a son with the condition — Williams expressed regret at her actions, saying sorry to Bighill personally on Twitter and making a donation to both the American Cleft Palate-Craniofacial Association and Operation Smile. It was a stupid thing to do, but at least Wendy moved past it.

17. Kelly’s cry for help

Kelly Osbourne quite literally grew up in the spotlight. The daughter of the Prince of Darkness Ozzy became famous through the reality TV show about her family. But Kelly regrets how she treated her parents, saying she “did a lot of really, really stupid things” because it was her “way of crying for help.” Furthermore, Osbourne lamented “being disrespectful” to mom Sharon, stating that it was one of her “biggest resentments” because she loves her mum. “I hate the fact that I hurt her and my father,” she added. She's clearly grown a lot as a person!

16. Jennifer nose she shouldn’t have changed her hooter

Teaming up with the incomparable Patrick Swayze, Jennifer Grey wowed audiences in the 80’s blockbuster hit Dirty Dancing. At that point in time, Grey seemed like she could have grabbed any role she wanted. But soon after, there was a moment of self-sabotage that changed everything. The self-conscious American actress decided to have plastic surgery on her distinctive nose. She looked very different afterward. Sadly, though, she was left regretting having the procedure, stating, “I went into the operating theater a celebrity and came out anonymous. I’ll always be this once-famous actress nobody recognizes.”

15. Macca mourned breakup of Beatles

Sir Paul McCartney was half of the most legendary songwriting partnership in rock music history. But the former bassist for The Beatles still regrets the way that the Fab Four broke up. He told the Daily Express, “You’d have to say the way the Beatles broke up was a bit untidy, a bit ugly. We were such a great little band, it would’ve been nice to just continue on... The business side really crept in and got a bit sticky. I regret that.” So do we, Paul. So do we. At least he patched things up with John Lennon before his death.

14. She Cher didn’t like Miley’s VMA’s performance

Talking to USA Today in 2013, Cher opened fire on Miley Cyrus and her infamous VMA “twerking” performance. The “Believe” singer said, “She can’t dance, her body looked like hell, the song wasn’t great, one cheek was hanging out.” But the diva eventually apologized on Twitter, writing, “I’m a little ashamed. I didn’t keep my big opinionated mouth shut... What I should have said [is] ‘I didn’t like [the performance] that much, but she’s pushing the envelope, being an ARTIST.’” Whatever you say, Cher. Maybe we can just chalk it up to a generational miscommunication.

13. Kanye candid on his biggest regret

Kanye West has achieved a lot in life — from releasing number one singles and albums to designing his own trainers. But in 2014 the outspoken rapper revealed on tour his biggest regret: that his late mom Donda never got to meet his daughter North. West said, “These past ten years have been amazing. There’s only one thing I wish I could change out of everything that’s ever happened. I wish that my mother could’ve met my daughter.” It just goes to show that no matter who you are, family is the most important thing.

12. Stevie’s short-lived marriage

Stevie Nicks was an important component of rock band Fleetwood Mac before enjoying a successful solo career. But what is the singer’s biggest regret? It wasn't any of the internal turmoil within her band. In reality, it was marrying Kim Anderson, the widower of her bestie Robin Snyder. Nicks told The Guardian about the hostile reaction, “It was insanity. Everybody was furious. It was a completely ridiculous thing. And it was just because I had this crazy, insane thought that Robin would want me to take care of [her infant son].” The union was unsurprisingly short-lived.

11. Whitney’s wistful wish

In case you didn’t know, The Hills alum Whitney Port has her own podcast. And on the aptly titled With Whit, she revealed a remarkable regret: passing on a night of passion with Leonardo DiCaprio. Yes, after meeting the Oscar-winning actor at a Manhattan party in 2009, Port claims that they swapped cell numbers before he asked her if she would come to his place. The reality TV star divulged, “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.”

10. Cuoco’s cunning cover up

When Kaley Cuoco married ex-tennis player Ryan Sweeting she got the roman numerals of their wedding date tattooed on her back. But when they split, the star was left with some unwanted ink. So The Big Bang Theory actress decided to get a moth inked there. But why that? Well, talking on The Ellen Show in 2016 she explained, “Because it was big enough to cover the numbers... The wings. Big wings.” Furthermore, Cuoco amusingly wrote on Instagram, “The deep, meaningful, larger than life meaning behind this beautiful piece of ink, is... It covered the last one.”  

9. Kenny could’ve been a better father

Kenny Rogers shifted over 120 million records in a career spanning six decades. That's hard to complain about. But the late country hitmaker regretted being an absent father to his two eldest sons. Back in 2013 he told country music website The Boot, “I missed an important part of their life. I look back on my career and I say, ‘Suppose I hadn’t been selfish? Suppose I had been the father I should have been, would I be here today?’ There’s a point where you have to say, ‘It doesn’t matter what I did.'”

8. Alba’s awful ink

Who hasn’t done something they now sincerely regret when they were younger? We bet you have, reader. And actress Jessica Alba has too, and she's been quite honest about it. The Dark Angel star told website Refinery29 that if she had her time again she’d never get that flower tattoo on her neck. Alba said, “I’m so irritated that I got it. I got it lasered many times and it’s not coming out.” The mother of three is not keen on the bow in the middle of her lower back either, remarking that it feels like “kind of a tramp stamp.”

7. Usher’s upset

Usher is surely proud of how he conquered the charts with his raunchy brand of R&B. But the “Yeah!” singer will always regret not spending more time with his dad before he passed away. The pair had been estranged for most of Usher’s life, but he said, “Instead of being there when he was sick, I was working. There was no amount of money that could have fixed my father’s health, but I could have just spent that time with him.” With any luck, that experience taught him to value his time with his loved ones a little bit more.

6. To be Franco, James regrets doing this

James Franco has a very specific relationship regret that makes him seem rather callous. The Pineapple Express star told Variety, “There was one instance, this old girlfriend was visiting me in New York. I had come out here for school. My cat had scratched her in the eye. I had so much work to get done for the next day, I didn’t take her to the hospital. I had my assistant take her. That moment haunted me so much. What kind of selfish, self-centered boyfriend are you?” A very sorry one by the sound of it, James.

5. Kris cross with herself for divorcing Robert

Kris Jenner is known worldwide as the mom of Kourtney, Kim, Khloe and Rob Kardashian plus Kendall and Kylie Jenner. But the self-styled “momager” has expressed regret at the split from her first husband, the late Robert Kardashian. The marriage ended after Jenner’s affair with soccer player Todd Waterman was uncovered by a private investigator hired by Kardashian. Jenner later remarked, “When I look back on it now, probably one of my biggest regrets in my life is that that marriage fell apart.” Mind you, Kris and Robert’s relationship began with an affair, so the former lawyer of O.J. Simpson could hardly complain.

4. Stewart still stews over cheating on co-star

When an unnoticed paparazzi photographed Kristen Stewart kissing director Rupert Sanders, it caused a media furor. The Twilight star was dating co-star Robert Pattinson at the time. And duly released a statement saying, “I’m deeply sorry for the hurt and embarrassment I’ve caused to those close to me and everyone this has affected. This momentary indiscretion has jeopardized the most important thing in my life, the person I love and respect the most, Rob. I love him, I love him, I’m so sorry.” The relationship, though, would be irreparable, despite Stewart’s contrition.

3. Miley’s major mistake

Miley Cyrus doesn’t really have the manner of someone with a lot of big regrets. But the former Hannah Montana star revealed on the Zach Sang Show that she wishes the famous video for her mega-hit “Wrecking Ball” — and indeed the song itself — were never created. Now, Cyrus wants to kill the song. “Swinging around naked on a wrecking ball lives forever,” she said on the radio show. “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. Calvin swiftly regretted Taylor rant

After Calvin Harris split up with Taylor Swift in 2015, the Scottish DJ went on something of a Twitter rant. It was seemingly sparked by a leak about how Swift wrote his mega hit “This Is What You Came For.” He would be left regretting his tweeting tirade, however, telling GQ, “It was completely the wrong instinct. I was protecting what I see as my one talent in the world being belittled. It felt like things were piling on top of me and that was when I snapped.” High-profile celebrity breakups certainly don't sound like fun!

1. Ariana’s Grande error of judgement

In 2019, Ariana Grande decided to get a permanent memento of her hit single “7 Rings.” But, that bit of ink wasn't applied exactly according to plan. Regretfully for the pint-sized singer, the tattoo on her palm didn’t read “7 Rings.” Bizarrely, it ended up reading “Japanese BBQ grill.” At least Grande saw the funny side of the mishap, writing on her Instagram stories, “RIP tiny charcoal grill. Miss u man. I actually really like u.” Get some Japanese lessons booked, Ari. Needless to say, she'll double-check her next tattoo design before the needle comes out.