Whether it was losing out on love, a lucrative deal, or even something as simple as a fashion faux pas, they’re still haunted by these moments in the past. Luckily, they’ve come forward to share their life’s biggest regrets, showing us that they’re only mortal beings after all! Read on to discover what makes Kim K’, Oprah, George Clooney, and more cringe to this day.
Usher Didn't Square Things With His Dad
Chart-topper Usher has worked hard to get where he is today. In fact, he worked so hard that he didn't even get to spend the last few quality moments with his father during his final days.
Though the pair had been estranged for most of his life, Usher admits that it still hurts him deeply that he just couldn't get away from his work to spend time with his sick father. This sure teaches us that family is everything.
Viola Davis Couldn't Help It
Viola Davis opened up in a conversation with the New York Times about certain roles that she regretted playing. While the actress has been incredibly blessed when it comes to some very meaty roles, she is sorry about her part in "The Help."
The "How to Get Away with Murder" actress said she felt the voices of those characters were not heard. Davis felt that there were certain things racial dynamics that the movie never actually touched on.
Not Boyfriend Material, Franco
Many of these celebs are just such hard workers. It takes a lot of effort to get where they are. James Franco is no exception. The "Pineapple Express" star described a moment that he deeply regrets. According to the actor, his girlfriend at the time visited him while he was in New York.
His cat ended up scratching her eye. With all the work he was busy doing, he hadn't even paid any attention to her and got his assistant to take her to the hospital. The moment has haunted him ever since.
Kenny Was Never a Family Man
Country music star Kenny Rogers has sold roughly 120 million records over the course of his 60-year career. That's quite the accomplishment, a feat not only the truly dedicated can achieve. When it came to his music, nothing was more important, which sadly why he neglected other aspects of his life, namely, his kids.
The American music star opened up to The Boot and revealed that he missed out on his kids' lives while acknowledging that he wouldn't have been able to become who he is today had he been the father he "should have been."
Jennifer Nose Best
The 1987 classic "Dirty Dancing" captivated audiences around the world, and while all those wild and sensual moves helped, it was also the very unique face of its leading lady, Jennifer Grey. The young actress had a distinct look, mostly thanks to her big and beautiful nose. Unfortunately, she felt differently about it.
According to the actress, she entered that operating theater a somebody and came out a nobody, adding, " I’ll always be this once-famous actress nobody recognizes." The irony!
Kristen Still Mourns Twilight Affair
Ah, "Twilight." Those were the days. The classic film franchise captivated a generation of young vampire and werewolf lovers, and that was largely due to Kristen Stewart and Robert Pattinson's electric onscreen chemistry, which shortly evolved into an offscreen romance.
Sadly, it came to an end when Kristen was papped, kissing the director Rupert Sanders. After the public scandal, Stewart released a statement apologizing for her actions.
Whitney's One and Only Wish
The MTV reality show "The Hills" was a show about a bunch of lucky young men and women living the good life in LA. Their flashy lives became the envy of many, but even these folks have things they missed out on. One of the women featured on the show named Whitney Port, spilled her biggest regret on her podcast "With Whit."
The reality star had her big shot with Leonardo DiCaprio but apparently just got "too nervous." Port admitted that she was just too nervous about being alone with him. We can understand how that would be a huge regret.
Cher Was Too Vocal About Poor Miley
Remember the 2013 VMA's when Miley Cryus went full twerk? There were some mixed feelings flying around that night, but one woman made her feelings heard, and that was a fellow pop star, Cher. The veteran singer took to Twitter and said posted a rather prickly comment over her Miley's dance moves and body.
Thankfully Cher saw the error of her ways and apologized for her comment, admitting that she should have perhaps kept her comments to herself. We agree with you, Cher. The ladies of pop should stick together.
Lamar Odom Misses Khloe
Lamar Odom was famously married to Khloe Kardashian from 2009 to 2016, but they were not all happy years. The former basketball pro was not always faithful to his wife. The infidelity resulted in divorce and a very sorry Lamar.
The ballplayer, who revealed all in his tell-all memoir, spoke about how those chapters were truly the hardest to write about. While Khloe has moved on, Lamar, unfortunately, feels that she is still his girl.
Robert Pattinson Should Have Never Been Edward
It's not rare when actors regret their roles, even ones that are so iconic. That's certainly the case for Robert Pattinson who rues the day he signed on for "Twilight." The actor felt he just couldn't do the character justice.
The actor joked, "I read the script; the more I read, the more hated this guy." In the end, he opted to portray him as a pretty miserable dude. We got to say, it worked.
Kris Still Sorry About Divorce
Long before Kris Jenner became known as the "momager" of the most powerful family on reality television, she was the wife to the infamous lawyer, the late Robert Kardashian. The marriage came to an end after some infidelity on Kris's part with soccer player Todd Waterman.
These days, Kris feels a lot of remorse over her failed first marriage and has been outspoken about how her biggest regret is the fact that she allowed her marriage to fall apart.
Bieber Dissing Lohan
From his teen loves to crazy nights, it's been quite the ride for little Justin (who is admittedly is not so little anymore.) We're sure that his rock-star life in the public eye hasn't been a walk in the park, which is why we're not particularly surprised that he has some regrets. One of them, however, is a true testament to his maturity.
When the gossip mags were comparing his unruly life to that of Lindsey Lohan, Bieber made a little jab at the former teen star by referencing her 2012 tax scandal. Fortunately, he removed his post shortly after, realizing that that was the wrong move. Good on you!
Kelly Looks Back on How She Treated Her Parents
When "The Osbournes" exploded onto our screens in 2002, Kelly Osbourne was only seventeen years old. An age ripe for teen angst and a typical "I hate my parents" sort of attitude. And if you've watched the show, you know that to be true. But as a grown woman in her 30s, Kelly now deeply regrets how she behaved.
Now a TV personality (and fashion designer) in her own right, Kelly said she was downright disrespectful, especially to her mom Sharon. We are sure your parents forgive you, dear.
Burt Played the Field
If we had to put a face to 1970s masculinity, it would be the Burt Reynolds. With countless women chasing that iconic mustache, the man sure did break a lot of hearts, but lo and behold, he got his heartbroken too! In 2015, the late actor told "Vanity Fair" that his biggest regret was losing the love of his life Sally Field.
Reynolds admitted that in retrospect, it was stupid to let her go like that, saying that you can find the perfect person and then do everything possible to mess it up. The actor missed her terribly until the very end.
The Brutish Crosby
In 2019 director Cameron Crowe released the documentary "Remember My Name" about the late legendary singer and musician David Crosby. As the central figure to both The Byrds and Crosby, Stills & Nash, David Crosby made a huge contribution to American rock music. But all that comes at a price.
According to the late rocker, his music-making years were not his kindest. In the documentary, Crosby looked back on how he treated his peers, saying that none of those people spoke to him later in life and that some of the things he did were just awful. It's not easy being a rockstar.
Bad Ink For Kaley Cuoco
When the "Big Bang Theory" star Kaley Cuoco wed the ex-tennis star Ryan Sweeting, she sure was smitten. So much so that she decided to get the Roma numerals of their wedding date permanently inked on her upper back. But then they split up, and she was left with the sad memory. Yikes.
The actress opted for a butterfly with wings big enough to cover the letters. Well, butterflies do symbolize rebirth, so we guess that one worked out. Next time though, stay away from tattooing things about relationships.
Clooney Misses Central Park
George Clooney has reached sky-high levels of fame and has clearly led a glamorous life. But with countless blockbusters, gorgeous women, and even success as a director, the actor has some regret about fame. In a 2014 interview with "Esquire," he said that the life of a celeb at times feels isolating.
In the interview, he continued by saying that he hadn't even walked in Central Park for over 15 years. Truthfully, that does sound a little hard, though we're sure many would be happy trade places with him.
No School for Sophie Turner
Many kids would have killed to get a part of the legendary "Game of Thrones," let alone miss a couple of years of school in the process. Actress Sophie Turner, however (aka Sansa Stark), feels a little differently about the whole experience. The English rose who worked on the show from age 13 to 24 revealed her true thoughts on the "The Graham Norton Show."
The actress admitted to Norton, “I wish I’d had the university experience." She continued to lament over the fact that she never got to experience her teen and college years going out with her friends without being photographed. Sometimes normalcy is all stars wish for. The grass is always greener, as they say.
Fatherly Advice for Kerry Cahill
"The Walking Dead" actress Kerry Cahill's expressed some heartfelt remorse to HuffPost in the year 2017. When she lost her father in 2009, she realized that there were so many things she missed about him; one of them was the little nuggets of wisdom he offered her throughout her childhood.
The actress revealed that she wished she could have sought out more advice from him on love and relationships; the advice might have helped her get through some hard relationships.
Ozzy Was Never a Musician
Black Sabbath's legendary frontman Ozzy Osbourne has clearly done a solid job being at the helm of one of the most significant metal bands of our time. With music pumping through his veins, you would think that that the rocker would know how to strum a riff or two. But apparently, this is not the case!
Ozzy told "Rolling Stone Magazine" that he deeply regrets not learning how to play an instrument. Aside from some harmonica, he has no real music knowledge. He does, however, have an ear for melody, and that is something every Sabbath fan can attest to.
Huey Never Sold Out
Frontman Huey Lewis of the iconic band Huey Lewis and the News was killing it back in the '80s with records flying off the shelves. As a band, they certainly were not struggling financially. But apparently, according to Huey, they could have done better.
In an appearance on "Jimmy Kimmel Live," Lewis spoke of his regrets during his music career. The rocker told the talk show host that around the same time that Michael Jackson got his $50 million Pepsi ad, Coca-cola offered them a similar deal, asking them to use “The Heart of Rock & Roll” in a commercial. He turned it down, a decision he now describes as "stupid."
Miley Wrecked It
There's no doubt that the mega pop star Miley Cyrus has taken some bold risks throughout her career. Shedding her innocent kid star act as Hannah Montana and evolving into the grown-up she is now has been a real journey, and along the way, she, unsurprisingly, has had some regrets.
The singer revealed she wishes "Wrecking Ball" never happened. Cyrus deeply regrets swinging around on a wrecking ball with no clothes on. Sigh, we hear you.
The Performance That Winslet Regrets
Considering the monumental success of "Titanic," one would think that the actors feel a sense of pride for their performances in the classic film. Leo, perhaps, but Kate, not at all! The English actress shudders over her over appearance in every single scene and is even more ashamed over her American accent, which she claims she "can't even listen to."
To be fair, many actors are critical about their work, but this one takes the cake. According to the English rose, if she could get the chance to redo that film, she would in a heartbeat.
Sheen Feels Guilty Over Cryer Comments
We're sure Charlie Sheen has a list of regrets, but there is one thing in his unruly life that seems to stand out, and that is what he said about his long-time "Two and a Half Men" costar Jon Cryer. The story goes that Sheen accused him of being a "traitor" for not contacting him after departing from the show.
Sheen later came forward to share his regrets with "Playboy Magazine," saying that he was wrong. He shouldn't have said that. He then added, "he’s a beautiful man, and I miss him."
Calvin Sorry About Swift
The Scottish DJ Calvin Harris was once smitten with Taylor Swift, which is why he went on a little bit of a Twitter tirade when it all came to a crashing halt. The reason was over a falsely published story about how the songstress got credit for the mega-hit "This Is What You Came For," a song that he penned.
He took to Twitter to try to get things straight; in the end, he came off just plain bitter. The musician later told "GQ Magazine" that he was only trying to protect his career, but in a way that he now regrets.
Garner Ran Down the Aisle Too Soon
Jennifer Garner has had a pretty interesting love life. After ten long and rather complicated years with Ben Affleck, the actress took the plunge and called it quits. But since it'd been so long, one might easily forget her marriage to another fellow actor, Scott Foley, all those years ago.
And this is Jen's greatest regret, marrying too soon. Back then, in the year 2000, the actress was starring on the hit show "Alias," and Foley was on "Felicity." Even though the "13 Going on 30" star was in her late 20s at the time, she admitted that she did not quite know what she had gotten herself into. When they got divorced, she revealed that she found it a “crushing experience.”
Goodbye to The Beatles
Considering the popularity of the Beatles, their lifespan as a band was super short-lived. The dissolution of the iconic British rock group marked the end of an era, singlehandedly devastating fans around the world. Some members would have had it differently if they could. At least Sir Paul McCartney.
He told the Daily Express that the way things got ugly towards the end. According to Paul, it was the business side that started to make things turn a little sour. The rock icon lamented about nice it would have been to continue. We hear you, Paul, we hear you.
The West Family Tragedy
It's no secret that Kanye West has grappled with a lot of issues in his life; it's amazing that he has accomplished so much. From countless hits to his fashion label, the rapper is a force to be reckoned with. He owes a lot of his success to his later mother, Donda, who was his manager until her final days.
Looking back on his life, Kanye is sorry about one thing, and that is that his mother never got to meet his kids. That does sound truly painful.
Oprah Looks Back
Oprah has undeniably made a string of smart business decisions when it comes to her career. The entertainment mogul has managed to rack up a net worth of $2.9 billion. But even with that amount of success, creating an empire has not always been easy.
Recently the talk show queen admitted that while she is very happy with her own channel and magazine, she sees now in retrospect that she spent too much time fussing over things that ultimately mean nothing. We must say, it looks like you did okay either way.
Alba’s Ink Fail
If you're going to do something that you regret, best do it when you're young and stupid, right? Jessica Alba knows that! She, too, regrets a tattoo she got done back in the day. The "Honey" actress told Refinery29 that she seriously regrets the flower tattoo she got on her neck.
She has even gone as far as getting it lasered multiple times, yet it just remains. As a matter of fact, the mom of the three isn't a fan of her lower back tattoo either. There's a special nickname for those, so we understand why.
Kim K's Engagement Post
Kim Kardashian has made some interesting choices when it comes to her love life. Looking back at some of her past lovers (ahem, Kris Humphries), we wouldn't be surprised at feelings of regret. But funnily enough, that's not what keeps her up at night. She revealed on Patrick Starr’s YouTube channel what does.
The Reality TV queen said that one of her biggest regrets is the photo she posted for her engagement to Kanye West. "I had the shortest nails when I showed my picture. It would have looked so much better with long nails." Sorry, Kim.
Wendy Gave Too Much Lip
It shouldn't be surprising to anyone that Wendy Williams let another eye-brow-raising comment slip out. The talk show host is no stranger to controversy, but when her comment caught the attention of Cher and even football star Adam Bighill, some people felt that she went too far.
Williams made fun of Joaquin Phoenix's cleft palate, and even though she found him "oddly attractive," people affected by the condition were not happy. In the end, the talk show host apologized on Twitter and promptly donated a sum to both the American Cleft Palate-Craniofacial Association and Operation Smile.
Benson's Hair Disaster
It may appear that Ashley Benson has it all. From the looks to the talent, the "Pretty Little Liars" actress definitely checks all the boxes, which makes this story all the more horrific. But one time, the actress almost lost all her hair due to botched bleaching at the hair salon.
Benson told "People Magazine" that this was her biggest regret. According to the actress, if you catch her in season three of the show, you can tell how terrible her hair is. If that's Benson's biggest regret, we say she's doing okay.
Ellie's Accent Blunder
Pop singer Ellie Goulding's career is still going strong, but a few years ago, things could have seriously tanked for her. The songstress recalled how early on, she worked hard to conceal her real accent and trained herself how to talk "posh" in order to hide her working-class background. Naturally, this is something she regrets.
Goulding revealed to "The Observer" that she became obsessed with speaking well. She said she just felt that people knew she was a poor girl from a council house, so she did everything she could to change it. In retrospect, the singer now feels silly about all that and has said that she is no longer ashamed of her accent.
Katherine Heigl Knocked It
While the Seth Rogen comedy "Knocked Up" catapulted Katherine Heigel's career, she has some qualms about how the film turned out. The actress said in an interview with Vanity Fair that the film was a little misogynistic and that she didn't actually feel that her character was likable. Unfortunately, her comments got her heaps of criticism.
Heigel then tried to straighten things out on The Howard Stern Show by saying that she enjoyed the movie, but she still felt like her character was just a little problematic. Seems like Heigl just can't win.
Grand Misjudgement
After her hit single "7 Rings," Ariana Grande decided to commemorate the accomplishment by getting the song title tattooed on her palm - in Japanese. The tattoo was supposed to read as 七 (meaning seven) and "輪" (meaning "hoop," "circle," or "rings.) Unfortanunetly that's not what came out.
It turned out that the pop star got the words "Japanese BBQ grill" tattooed on her palm instead. Ari should have probably consulted with a translator beforehand!
Christina Applegate Illegally Blonde
The lovely Christina Applegate sometimes still kicks herself over, letting this opportunity pass her by. The actress had just finished up with "Married […with Children]" when a little script called "Legally Blonde" came her way. Applegate found herself fearing the typecast curse and therefore passed on the script.
While do not regret seeing Reese in the iconic role, We would have loved to see Christina Applegate give us Elle Woods.
Ben Regrets Divorce
Ben Affleck was once a loving hubby to the wonderful Jennifer Garner, but according to the actor, some of his demons crept in. In a candid interview with the New York Times, the actor revealed his very real struggles with addiction and how it became a contributing factor to the dissolution of his marriage, a fact he feels remorseful about to this day.
This sure does sound like a tough one. Well luckily for Ben, it seems that another incredibly famous Jen...ahem...Jennifer Lopez to be exact is willing to give Marriage with him a go.
Pete Who?
Legendary rock band The Who have earned their spot in the list of rock 'n' roll greats. Unfortunately, given then the opportunity to do it all over again, the band's lead guitarist Pete Townshend would have opted out of the whole experience.
In an interview with Uncut Magazine, he said that given a chance, he would never have joined a band because he's bad at collaborating. Fortunately for music lovers around the world, he made the wrong decision and joined them anyway.
Sabrina's Lost Love
In 1996 "Deadpool" star Ryan Reynolds was an up-and-coming teen heartthrob who got a lucky little gig on the TV movie "Sabrina, the Teenage Witch." The popular film which starred the iconic Melissa Joan Hart ended up inspiring a whole TV series. The two had a very brief teen fling on set. Too brief, unfortunately.
Sadly things fizzled out shortly after. Hart told Studio 10 in Australia that even though the pair were completely smitten, she decided that ultimately she wanted to stick with her boyfriend at the time. Oh, what could have been.
Nick Lachey's Bad Move
As a pop star, sometimes you get thrown into different projects that arent' exactly about singing. It's not uncommon for mega music stars to score their own reality shows; it happened with Britney and, again, with the "newlyweds" Nick Lachey and Jessica Simpson.
Looking back, we know those two were ill-suited, and the whole marriage was a mistake, but Lachey specifically regrets the TV show. Nick Lachey admitted to David Letterman that Newlyweds: Nick and Jessica" was the worst thing he'd ever seen. Yikes!
The Reality Show That Britney Regrets
Back in the 2000s, Britney Spears and Kevin Federline were a thing, which is something the whole world probably doesn't look back on too fondly. So it's not surprising that Britney herself has some regrets, especially when it comes to the ghastly reality show "Britney and Kevin: Chaotic."
The pop sensation told the British newspaper "The Telegraph" admitted that the series was actually the worst thing she did in her entire career and that given a chance to do it all over, she would have never said yes to the cringe-worthy series.
Justin Timberlake Failed Janet
Remember the infamous Super Bowl halftime show? The one where Janet Jackson had a wardrobe malfunction on stage? Yep. We do, and so does Justin Timberlake. The pop singer who was right up there with her and regretted the way he handled it.
Jackson's career took a hard knock, while Justin's flourished. He didn't even say a thing to protect her from all the hate. Needless to say, he's sorry about it now.
When Stevie Nicks Said "I Do"
Fleetwood Mac's Stevie Nicks has led a long and successful career, both as a band member and solo artist. As a band member, especially in the era of hippie love, she got herself into some interesting entanglements. But before her iconic romance with fellow bandmate Lindsey Buckingham, the rock queen tied the knot to Kim Anderson, the widower of her best friend, Robin Snyder.
But that knot came undone very quickly, within the year to be exact. And it was a move that upset a lot of people. According to Nicks, she just hoped that he would take care of her and her infant son. We suppose they never continued long enough to find out.
Mariah Carey's "G" Word
If Mariah Carey could take back one thing she did in her entire career, it would be the film "Glitter." During an appearance on "Watch What Happens Live," she got real with host Andy Cohen and said that she hates that film so much that she doesn't even let anyone discuss it.
The singing sensation who has dubbed the bad decision as "the G-word" expressed a lot of remorse on the talk show but still took the time to acknowledge the learning experience and how she has since grown. Good for you, girl.
Megan's Marilyn Tattoo
Remember Megan Fox's giant tattoo of Marylin Monroe on her arm? Apparently, once upon a time, she was really into it, but some years later, the "Transformers" actress ended up getting it removed.
When asked in an interview about why she made that decision, Fox said that she felt the legendary actress was a person with an energy she did not want in her life. We thought Marylin was a saint!
Courteney's Fillers
Our "Friends" darling, Courtney Cox, has expressed some regret over her cosmetic surgery. In an interview with "New Beauty Magazine," the actress stated that it took some time for her to notice the effects the procedures had on her face as it was such a gradual process (and looks worse in photos.) But when she did, she decided to undo all the work she had done.
That meant dissolving the fillers in her face and keeping up with a more natural look. These days, the actress said she "feels much better because I look like myself. I think that I now look more like the person that I was. I hope I do."
Aniston Regrets the Rachel
Ah, the Rachel. The mid 90s hairdo made waves around the world, prompting every woman (and definitely some men) to rush to the hair salon in pursuit of the iconic look. But what did it do to the woman who originated it? Well, the OG Jennifer Aniston actually admitted that she really regrets it.
She told "The Telegraph" that she thought it was the worst haircut she's 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.”
Beckham's Embarrassing Hairdo
Over the years, David Beckham has displayed a wide range of iconic looks. Some of them, total hits (remember 1998 - the year of the sarong?) but then 2003 rolled around, and the soccer player ended up getting cornrows. In retrospect, this style can be viewed as a bit of a mistake, and Beckham sure does agree.
He admitted on the "The Graham Norton Show that “[They] were maybe a bad decision!" On top of that, he got them at an awkward time - just before a trip to South Africa. The football star ended up meeting the legendary former president Nelson Mandela with his interesting hairdo. Defiteingely a good reason to regret it.