Celebrities Share Their Biggest Regrets
When we think about celebrities the first thing that comes to mind is fame and a lavish way of life. We hold them in high regard and see their lifestyle as something to aim for. Gorgeous dresses, fancy cars, and incredible houses, they have it all, which is why it’s sometimes hard for us to remember that they’re ordinary people just like us. To remind you of that fact we’ve compiled a list of some of their biggest regrets and what led them to them. From career failure, fashion disasters, surgical mishaps, and personal drama.
So grab your popcorn, make yourself comfy, and have a look at what these high-profile celebrities regret most!
Miley Cyrus
Miley started off her professional life at the early age of eleven, when she auditioned for the Disney channel and eventually got to play Hannah Montana. From that point on her career boomed and she went on to release music and act in some of our favorite shows. But growing up as a talented actress/singer can take a toll on you, mentally, physically and emotionally. Over the years she ended up doing some things that in hindsight she regrets.
When we think about Miley today the first thing that will probably pop into our minds is the wrecking ball music video. In an interview with Zach Sang she admitted that this video was the thing she regretted the most in her professional life “That’s something you can’t take away, swinging around naked on a wrecking ball lives forever”.
Sophie Turner
Being a young actress can be thrilling and exciting, you get to wear fun costumes, meet famous people, and be an inspiration for young people everywhere. At the same time though there are also setbacks to an early acting career. It can take a toll on you and as a teenager you can also miss a lot of crucial social events that most kids get to enjoy.
For Sophie, her biggest regret was just that, not being able to be a “normal” child growing up. Especially when it comes to life at a higher education institute. While filming Game of Thrones she didn’t get to experience college life, she said that she wished she could have “gone out and drunk a lot and thrown up in the middle of a club”.
Kanye West
He is one of the most controversial celebrities talked about, you either love him or hate him. Kanye has made a name for himself not only thanks to his music but also his unapologetic beliefs and views on life and how it should be lived. After numerous controversies, you’d think the rapper has many things to regret.
Surprisingly he doesn’t feel bad about much. YOLO mentality allows him to do whatever he wants without feeling the tiniest bit of remorse. Despite that he did have one thing he wished he could change, and that is to have more nudity in his Bound 2 video. The reasoning behind it will surprise you, according to him “I just want to do crazy, colorful s*** like that that has more nudity”.
Kate Winslet
Making a movie takes a long time and it’s not uncommon for cast members who never met each other to become great friends during this time. Leonardo DiCaprio and Kate Winslet first met on the set of 1997 Titanic, playing the roles of Jack Dawson and Rose DeWitt Bukater respectively. In an interview Kate said that at first she was worried that Dicaprio would find her “all stuffy and Shakespearean and English”. Fortunately both clicked immediately and became close friends for the next seven months.
When Kate was asked about one thing she regrets, she replied that the sex scene had to end. Although the two didn’t have any romantic relations or feelings for each other, the actress admits that it’s because of the lack of such feeling the scene wasn’t a lot of fun to shoot.
Robert Pattinson
Every aspiring movie star’s dream is to play the leading role in a blockbuster movie. However the fame, money, and recognition that comes with being successful can sometimes be overwhelming or even lead to some negative outcomes. Many actors who played leading roles in popular movies couldn’t shake that character off them later on in life. No matter how many roles Daniel Radcliffe will play in the future, he will always be Harry Potter for most of us.
A similar fate befell Robert Pattinson when he played the role of Edward Cullen in the Twilight saga. Although the movies were an enormous commercial success, putting Robert in the Hollywood spotlight, he could never shake the Twilight role off. He said that if he could go back and change one thing he would’ve stayed away from the franchise.
Jennifer Aniston
All of us at a certain point in life embraced a fashion statement that we thought was the best thing since sliced bread. Be it in our teens or early 20s, we all thought that our fashion choices and lifestyle were the best and everyone who didn’t think so was wrong. For Jennifer and many others in the ’80s and ’90s it was sunbathing with baby oil.
She admits that it wasn’t one of the best things to do and for good reason, it can lead to skin damage and cancer. These days Aniston is very vigilant when it comes to taking care of her skin, as the representative of Aveeno skincare she makes sure to watch herself. That might be why she confessed to carrying an SPF 70 sunscreen with her at all times.
Justin Timberlake
Over the years Justin has dipped his fingers in many forms of entertainment, starting with the leading boy band NSYNC and then a solo career, to playing in movies and voice acting. The undoubtedly talented singer/actor is leading a rich and diverse career for himself, which is why he is on this list. While filming The Mickey Mouse club, Timberlake and Britney Spears met for the first time and announced their relationship seven years later.
After their breakup, he admitted that he made some “missteps” that he believes led to “a system that condones misogyny and racism.” Additionally, he confessed that he should have supported Janet Jackson more after the 2004 Super Bowl wardrobe mishap.
Courteney Cox
Aging is a tough thing to accept, we all want to keep our youthful looks and not have back pain every morning. This idea of looking young is even more relevant to celebrities that thrive off of good looks (and good acting skills). Some go to great lengths to try and retain their young looks just to end up looking disfigured and alien.
Luckily for Courtney Cox, she realized the error of her ways early on when she just started getting face fillers done. It was a process that took time. Cox said that “You need movement in your face, especially if you have thin skin like I do,”. It took her a while to get used to her face moving again and she had to go through some soul searching to be at peace with her looks.
Ben Affleck
Live-action superhero movies are a highly debated topic among fans. There is a big discrepancy between the film and the comic on which it’s based, that’s why you either love them or hate them. Ben Affleck, much like other actors, has a movie that left a big fat stain on his career and led to fans questioning his performance in future films.
The 2003 Daredevil was Affleck’s biggest regret, everything from the story to the characters in this movie “got f***** up” the actor said. When the news came out that he was going to replace Christian Bale in the newest Batman movie, fans weren’t happy. However, Affleck reassured the fans that he was going to do his best to make up for the lacking performance in Daredevil.
Viola Davis
Many times we think that acting is a glamorous job, which it can be, but it’s important to remember that at the same time it can be really challenging. One of the biggest obstacles every actor needs to overcome in his career is playing characters outside of their comfort zone. Many times when we watch a movie or a show we don’t even think about how the actor felt while filming a scene.
Viola Davis took the role of Aibileen Clark in the 2011’s The Help, a role she has since regretted playing. The movie revolves around a white journalist who develops a relationship with two Black housemaids in 1963. Davis believes that the movie’s portrayal of Black maids was marginalized, focusing more on the “white savior” narrative.
Carrie Fisher
Relationships between celebrities aren’t an uncommon thing. When you share long periods of time with the same people you eventually connect, and in some cases develop relationships that can last a long time or even lead to marriage. For Carrie Fisher and Harrison Ford their relationship lasted for a couple of months and was nothing more than a fling.
Their affair began on the set of Star Wars when Carrie was 19 and Ford was 33, married with children. His now ex-wife didn’t know anything about the affair until it was revealed in an interview while Carrie was promoting her book The Princess Diarist. She later admitted that it was a mistake to immortalize her affair in the book and that perhaps it should’ve remained a secret.
Katherine Heigl
It has been fifteen years since the release of the great romcom Knocked Up starring Seth Rogan and Katherine Heigl. The movie had boosted the already successful actors’ career even further, putting them at the forefront of Hollywood celebrities. Heigl admitted that the movie was a great experience for her and she enjoyed it very much.
However, at the same time, she regrets playing the character of Alisson Scott, claiming that it felt a little sexist and that “it paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys.” To be fair, playing a character who is a killjoy can’t be all that fun.
Kris Jenner
Since airing their own reality TV show Keeping Up With The Kardashians, the family has been a source of entertainment, controversy, jaw-dropping drama, and inspiration for many years. But none of this could’ve been possible if it wasn’t for Robert Kardashian & Kris Jenner’s Marriage. They first met in California in 1973 and later Kris went on to have four children with Robert.
Unfortunately, their marriage didn’t last and the two ended up getting a divorce after Robert found out that Kris was cheating on him with the soccer player Todd Waterman. She admitted that she was in a bad place at the time and it was one of those situations where the grass is always greener on the other side, “When I look back on it now, probably one of my biggest regrets in my life is that that marriage fell apart.”
Mariah Carey
When you think of her the first thing that pops into your head is probably her amazing performance of “All I Want For Christmas”. But aside from her amazing voice and five-octave vocal range, she is also known for her infamous debut in the movie Glitter as Billie Frank. The movie was described by critics as “heroically bad,” and “too washed-out and worthless to even be so bad it’s good.”
The failed movie became a taboo subject to talk about around Carey and for a very long time was regarded as “the g word”. When she appeared on the show Watch What Happens Live she provided the host with several compelling arguments as to why the movie was such a disaster, for starters “there was no script”, and it was released on 9/11. At the end of the day when Mariah Carey goes to bed, the only thought troubling her mind is the regret of making that movie.
Howard Stern
In his early career, Howard had quite the potty mouth on him, being the star of a popular ’90s radio interview show that often aimed at disrespecting his guests. Stern developed a bad habit of being mean to his guests even when he didn’t want to. This led him to being unapologetically rude towards one of the nicest comedians and actors Robin Williams.
In an interview with the Rolling Stones Stern admitted that one of his biggest regrets in life was being an “assh*le” towards Williams despite acknowledging that he had deep respect and love towards him. “I love Robin Williams, and yet if he came into my studio, I had to act like I didn’t love him. I’d be, ‘Fuck you. Fuck you. I need all the attention,’”
George Clooney
He’s Hollywood’s most recognizable star, with dozens of movies under his belt and a luxurious endorsement contract with Nespresso. But did you know that his mainstream success didn’t come from movies but from television? He played on the 1990s medical drama, ER as Dr. Doug Ross, it was only after this show that he decided to make the transition to the big screen.
The downside of being a famous celebrity is that you will be bound to play in a bad movie or two, surprisingly enough for Clooney it was Batman & Robin. The DC fans’ opinion of the movie was never positive and it’s still considered to be one of the worst superhero movies of all time. In hindsight Clooney admits that he shouldn’t have taken the role of Batman to begin with and regrets it till this day.
Jay-Z
He’s considered one of the most talented rappers of his generation. He started his rapping career by selling his music from his car until he eventually started his own record label Roc-A-Fella Records. The early 2000s were the times when rap music flourished and many rappers made their best work that is remembered to this day, for Jay Z that song was Big Pimpin.
Unfortunately, many of his lyrics are considered racy and provocative when it comes to women. In one interview he said that he regrets some of the words he wrote and even went as far as to apologize for the song Big Pimpin. Till this day the song is considered to be one of the most influential songs he made and much of the album’s success is thanks to it.
Amy Schumer
On top of being a comedian, she also wrote, produced, and played in quite a few movies. But probably the first thing that comes to mind when you think about her is The Leather Special and how Netflix removed its rating system after it aired. Coincidence? You can decide for yourself.
People love to hate on Amy Schumer and not only because of her comedy bits, as a famous woman she was also the target of hateful comments regarding her appearance and weight. Despite all the haters she stood her ground and convinced the public that she will never undergo any cosmetic surgeries… except liposuction which she does NOT regret doing because “I was tired of looking at myself in the mirror”.
Hailey Bieber
Deciding which tattoo to pick is a very important decision, not only will people be asking us the meaning behind it for as long as it exists. But more importantly, we might change our minds about it. The topic of tattoos can sometimes be very controversial where some think that it’s a waste of money and time while others see it as an expression of themselves.
This can be especially important when your body is your work, Hailey Bieber has around 20 tattoos on her and all of them have a meaning. In an interview, she admitted that she regrets having one of her earlier tattoos, the little gun on her finger. The model got it when she was 18 and there wasn’t really a reason behind it other than “it looked cool”. So next time you are going to get a tattoo, think to yourself, “will future me be happy with it?”
Victoria Beckham
Having a positive body image is very important, we all suffer to a certain degree from negative body image and wish we could change a thing or two. But changing something over and over again can sometimes lead to negative outcomes, how many times have we seen celebs with cosmetic surgeries gone wrong?
Victoria has gone up and down in cup size over the years and the surgeries have taken a toll on her body. She ended up regretting the procedures and stating that it’s best to celebrate what you have. Ever since the realization she abstained from unnecessary body changing surgeries and stuck to changing only her hairstyle, accessories, and fashionable clothes.
Madonna
Being a successful celebrity is difficult, not only do you have to deal with all the fans and paparazzi but you are also swarmed with movie role offers all the time. Madonna is one of the most famous and known singers in the world, she composed dozens of songs and acted in her fair share of movies.
But there are a few parts that the diva had to pass on and she regretted it ever since. In her latest appearance on The Tonight Show she revealed that she was offered a role in the 1999 The Matrix “A teeny-tiny part of me regrets just that one moment in my life.” But the regret doesn’t stop there, Madonna also missed out on playing Catwoman in 1992 Batman Returns “I saw them both and I regret that I turned down Catwoman, that was pretty fierce”
Britney Spears
Britney is a legendary celebrity icon with dozens of popular hits under her belt like “Toxic” and “Oops…I Did It Again”. Through her career, she dealt with many scandals and was criticized so much that it sparked the infamous “Leave Britney Alone” video that we still look back on today. No doubt Britney had her fair share of turmoil under the spotlight, and if there’s one thing the diva regrets the most is making Britney and Kevin: Chaotic.
The reality show which features Britney and then-husband Kevin Federline gave fans a glimpse into the couple’s daily lives. In hindsight putting your love life on display for everyone to see is not the best idea.
Rihanna
Award ceremonies are great opportunities for celebrities to whip out an incredible ensemble and shock the crowd. The best outfits can be seen at the annual Met Gala exhibit where models and celebrities dress in the most stunning and outrageous attire you can imagine. But in Rihanna’s case, you don’t have to wait that long to see her in a stunning dress walking down a red carpet.
Back in 2014, she made the world gasp in awe as she appeared on the CFDA Fashion Awards in a gown made entirely out of Swarovski crystals. When interviewed later she said that she regrets wearing a thong as it made outlines in the dress “I just liked it better without the lines underneath” which explains why she didn’t wear a bra as well. It seems that her life is heading the right way if her biggest regret in life is wearing the wrong thong.
Bill Murray
One of the most renowned actors in Hollywood history, with movies such as Ghostbusters, Groundhog Day, The Jungle Book, and Lost in Translation, to name a few. Without his contribution to the world of movies, we’d be missing out on a whole lot of classics. Being so involved in the industry is bound to produce one if not a few cinematic “failures”.
In Murray’s case, his biggest regret was taking part in the Garfield movies. His biggest mistake was not checking who was the writer for the movie, at first, he thought it was Joel Coen, the creator of cult classics like Fargo, No Country for Old Men, and The Big Lebowski. But instead it was Joel Cohen who was not as renowned a writer.
Bill Gates
Being the head of a successful multi-billion dollar company, a father and a husband is no easy task. According to Forbes, Bill Gates has an estimated net worth of $124 billion, and his company Microsoft has a market cap of $2 Trillion. In September of 2019, Netflix aired a show called Inside Bill’s Brain: Decoding Bill Gates in which the audience could have an insight into his philanthropy work and life as a father and a husband.
During that show the director, Davis Guggenheim, asked him what his biggest regret was. The now divorced Billionaire said he should’ve thanked his wife more. The couple had met when Bill just started Microsoft and Melinda was their product manager. After some back and forth the couple decided to take a big step forward and get married and have children. The details of their divorce are unclear but a Twitter post made by the couple stated that they “no longer believe we can grow together as a couple in this next phase of our lives”.
Whoopi Goldberg
The American comedian, producer, and actress is known for co-hosting the TV talk show The View and her stunning performance as Celie Johnson in the movie The Color Purple. Throughout her career she befriended many artists and actors, One of which was Sammy Davis Jr. They became close friends and she considered him to be one of the greatest musicians of all time right next to Frank Sinatra and Michael Jackson.
In 2011 the co-host of The View and actress was a guest on the Piers Morgan Live, when she was asked what her biggest regret she replied, “I had the opportunity to spend a birthday with Sammy Davis Jr., and I didn’t.”. She didn’t have an exact reason as to why she decided not to go and her only excuse was that she was young and dumb.
Jennifer Lawrence
Friendship tattoos are a great gesture, it shows that you care for the person enough to go through a session of pain and suffering as needles are jammed into your skin repeatedly. But what happens when the tattoo idea you thought was great turns out to be not so great and you made it someplace anyone can see? That’s exactly what happened to Jennifer and Liam Hemsworth.
While both were young sprouts on the set of The Hunger Games they decided to have a bonding session in the form of matching tattoos. For whatever reason, they decided that the best idea would be to get the H2O symbol and Jennifer went one step further and did it on her hand. Although she now considers it to be her biggest mistake, the fact that you can still see it on her hand is a sign that she came to terms with it.
Kim Kardashian
Kim Kardashian’s divorce from her now ex-husband Kanye West hasn’t exactly been a clean one. West isn’t shy when it comes to voicing his opinion or crapping all over his ex’s new beau Pete Davidson. Despite all the turbulence, there’s one regret the Kardashian has when it comes to her marriage with West. And believe it or not, it has to do with a MAGA hat.
The two got into an argument when Kardashian wanted him to remove the red cap on TV, which he ended up doing. In retrospect she believes she shouldn’t have made that decision for him, saying, “Why should he take that off if that’s what he believes in?”
Whitney Port
We think most people who’ve seen Titanic have been wooed by Leonardo DiCaprio. He was a major crush for most of us who grew up with the film, who could resist that blonde hair and those boyish good looks? Well, turns out Whitney Port did and she’s regretted it ever since! Most of us wish we hadn’t participated in some one-night stands, but Port feels the opposite about this opportunity.
The actress admitted that back in 2009 she had the chance to get frisky with the actor, but ended up turning the offer down. She calls this one of her biggest regrets, and honestly, we can’t even blame her.
Lamar Odom
You might know Lamar Odom as a professional basketball player and former member of the Los Angeles Lakers. However, if you’re not into sports you might recognize him as the ex-husband of Khloé Kardashian. The two were married for seven years until their divorce in 2016. Odom was battling substance abuse, but that likely wasn’t the main reason for their split.
In his memoir, Darkness to Light, the former NBA player admitted to cheating on Kardashian. “I wish I would have treated her the right way,” he confessed. We bet a lot of cheaters feel the same regret he does, and we’re glad to see he’s cleaned up his old ways.
Jessica Biel
Being a woman in Hollywood isn’t easy, being a teen is even harder. Many former child stars have come forward to recount some pretty horrific events that they dealt with in the industry, which makes this regret of Jessica Biel even sadder. There are a lot of people out there who take advantage of famous teens, and Biel was, unfortunately, victim to one of them when she was signed up for a topless photoshoot.
“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,” Biel said. Though she admits she was able to learn and grow from the experience, she wishes she had never done the photoshoot in the first place.
Mary-Louise Parker
You’ll recognize this starlet from films like Fried Green Tomatoes and The Portrait of a Lady, as well as TV shows like The West Wing and Weeds. Apparently there was a moment in the latter series where she had some creative differences with the director over whether or not her character should appear nude. She ended up giving in to their request, though in hindsight regrets the decision.
She felt like it wasn’t necessary for her character to appear topless, and knew that the photo would inevitably be all over the internet for the world to see. “I wish I hadn’t done that. I was goaded into it,” Parker puts it.
Brad Pitt
Most of us still remember the days when Jennifer Aniston and Brad Pitt were the hottest celebrity couple. Then everything changed when he starred in Mr. and Mrs. Smith with sex symbol Angelina Jolie. Rumors swirled about the two having an affair on set, some even blamed Aniston for letting him act alongside Jolie in the first place! Turns out Pitt is the one with regrets after all these years.
Divorce is never a fun thing to go through, but the least both parties can do is make it as painless as possible. Apparently, Pitt feels he could’ve handled things differently, which to us sounds like a bit of an understatement!
Jada Pinkett Smith
If you weren’t aware, Jada Pinkett Smith has a quite open and honest talk show called Red Table Talk. The actress and her guests don’t hold back when coming clean about painful moments in their past, and in one episode Pinkett Smith shares one of her biggest regrets. Her guest? Sheree Fletcher, the woman who was married to Will Smith when she started pursuing him.
Pinkett Smith admits that she didn’t understand the seriousness of marriage and divorce and that she shouldn’t have gotten romantically involved with him while he was still with Fletcher. While Will does hold his share of the blame for cheating, we’re glad Jada was able to admit her fault as well.
Melissa Joan Hart
A lot of Hollywood romances start behind the scenes of a movie or TV show set. This was the case with Melissa Joan Hart and Ryan Reynolds, who both starred in the 90s series Sabrina the Teenage Witch. Young and in love, the two had a brief fling that didn’t end up going anywhere serious, though Hart wishes it had!
“He was sweet — he was very sweet,” she says about her time with the actor. At the time Hart had a boyfriend who she didn’t end up going long-term with, she wonders if Reynolds would’ve been the perfect match for her. As she puts it “Maybe I should have taken a chance!”
Kelly Osbourne
Being the daughter of a famous rockstar can’t always be easy, especially when your private life is broadcast on a reality TV show. It’s no secret that Kelly Osbourne has struggled with substance abuse in the past, but her biggest regret is actually something a lot of people might relate to. Growing up rebellious is natural for most teens, but Osbourne admits she took it too far.
“My mum’s my best friend. I hate the fact that I hurt her and my father,” she said, referring to her sordid past. She’s now an advocate for rehab when it comes to teens who are dealing with substance abuse. It seems she definitely learned from her past mistakes.
Jennifer Grey
You may be wondering why we didn’t use a more recent photo of this actress, and the answer is because you might not recognize her anymore! Most people remember Jennifer Grey as the goodie-two-shoes older sister from Ferris Bueller’s Day Off or the starry-eyed teen in Dirty Dancing. But one small surgery basically killed any further career she could’ve had.
She recounts how her mother used to tell her how she should go under the knife, ” I was so upset with my mother for always telling me I should do my nose.” Grey felt that she was beautiful enough and didn’t need to conform to superficial Hollywood standards. Nevertheless, she did get the nose job and, as she puts it, “I was no longer me.”
Christina Applegate
Married with children was one of America’s greatest sitcoms with networks worldwide copying the format and recasting it locally. Applegate played the older child in the Bundy family and embodied the classic “dumb blonde” character. After 11 seasons of family drama, the show was over and the cast all went their separate ways.
During that time Applegate felt like she exhausted the dumb blond character and decided to no play as one ever again. Unfortunately for her, it came right when she was offered the leading role in Legally Blonde. Unaware of how successful the movies would be, she rejected the role which then went to Reese Witherspoon and turned her into a huge star.
Cher
The American singer has an unparalleled career, she sold well over 100 million records and managed to jam pack arenas with screaming fans. It’s only fair to assume that somewhere along the way she made some mistakes or came across some mishaps that led to regretful memories. For Cher, these were actually Hollywood flings, or lack thereof…?
During her career she met many famous celebrities, some are still alive and some are not. One of those people is actor Marlon Brando, both had a hot but brief affair and her biggest regret is that she didn’t meet him sooner. Another remorseful memory she had was rejecting the king of rock and roll Elvis Presley, in an interview she admitted that the singer had invited her over for the weekend but she was too nervous to accept.
Eddie Murphy
Being a comedian these days is harder than ever before, you need to be careful of what you say lest someone comes up and slaps you on stage. Eddie Murphy has been in show business for a very long time, over the years he performed at comedy clubs, had legendary standup specials, and made several successful films. With such an impressive career there are bound to be several things that fans or haters can dig up and criticize him on.
For the longest time when Murphy was doing comedy, he was leaning heavily on jokes about gay men and AIDS. This has caused many rights activists to speak out against the comedian stating that he never apologized for his homophobic skits. In his defense Murphy ended up apologizing eventually, saying, “I think it is unfair to take the words of a misinformed 21-year-old and apply them to an informed 35-year- old man”.