Everyone has regrets. From the little things, like regretting that you missed out on your friend’s birthday, to regrets that could haunt your life for a long time, such as career mistakes, missteps with friendships, or doubts about letting that person who might have been “the one” slip through the cracks.
Celebrities experience both their careers and personal lives in the spotlight and we all know that their missteps play out in front of the public. Some celebrities have managed to admit to a few of the regrets they have had over the years. These have included everything from professional misgivings, such as George Clooney’s regret about taking on a certain movie role, to qualms about their own personal lives and families. It may be surprising who is on this list, and who isn’t on this list (former teen pop stars, we’re looking at you). But it is possibly even more revealing what, exactly, certain celebrities have regrets about (and what they haven’t fessed up to regretting... yet).
10 Britney Spears regrets “Britney and Kevin: Chaotic”
Pop star Britney Spears has had an impressive – if not turbulent – career that has earned her steady attention and fame since she was a teen. Despite the ups and downs in her life that have played out in the public spotlight such as dating (and allegedly cheating on) Justin Timberlake, having a brief 55-hour marriage, and shaving her head, Britney has said she doesn't have any regrets other than one thing. During an interview last year, she admitted her biggest regret was starring in a reality tv show back in 2005. Spears filmed the reality show, a 5-episode series called “Britney and Kevin: Chaotic” with her ex Kevin Federline during a European tour, calling it the worst thing she did in her career.
9 George Clooney regrets “Batman & Robin”
Nearly two decades after its theatrical release, it still comes up in interviews that George Clooney regrets playing the iconic comic book hero Batman in the 1997 movie “Batman & Robin.” When Clooney originally signed on to play the role, he was mainly known for his role on the NBC primetime drama "ER." “Batman & Robin” was his first big-budget action adventure film, and also starred Arnold Schwarzenegger, Chris O'Donnell, Uma Thurman and Alicia Silverstone. On Reddit earlier this year, Clooney admitted that he was not thrilled that he had once stepped into the film’s ridiculous-looking batsuit (which famously showed off his nipples). However, even though he thinks the film didn’t work out, he has also said it was a good experience on set working with the others. Clooney has admitted that at the time he got caught up in the excitement of being a part of the film and expected it to be a big hit. Unfortunately, the opposite happened. Despite having a production budget of 125 million, it only earned a domestic gross of 107 million. As we all know, Clooney is no worse for the wear; he went on to have some roles that were far from regretful and is currently enjoying a net worth of $160 million.
8 Oprah regrets time wasted on worries
Talk show host, media guru and philanthropist Oprah Winfrey has had many accomplishments in life and with a net worth of $2.9 billion, one might imagine few things to regret. But in a video that she posted following the cover shoot for her magazine this past April, she admitted a few regrets that she has about life that she has become aware of now that she is growing older. In the video, Oprah said that she regrets time that she has wasted in life and also regrets all of the things that she worried about that do not actually matter.
7 Kanye West regrets not featuring more nudity
The regrets that superstar singer/songwriter (and husband of Kim Kardashian) Kanye West admits to are probably not what you’d expect. First of all, and on a sweeter note, West has said that one of his biggest regrets is that his mother, Donda, died in 2007 and she is therefore not able to meet his daughter, North. Another regret is completely different: in the August 2014 issue of GQ magazine, Kanye told the magazine that he regrets not featuring more nudity with his wife (and North’s mother) Kim Kardashian in his Bound 2 video.
6 Bill Murray regrets “Garfield” (maybe)
Remember the 2004 movie Garfield? If not, no worries. Many critics gave it poor ratings and even the voice behind the famous cartoon cat, Bill Murray, probably wishes he could forget all about it. In a 2011 interview, Murray explained that he jumped on the chance to voice the role because he thought that his idol, comedy writer Joel Coen, had helped pen the script. However, it had actually been written by another writer with a similar name – a detail that he realized after he’d already signed on for the role. In 2009, Murray played himself in the movie “Zombieland,” and in a scene when he was shot, was asked if he had any regrets. He responded, “Garfield-maybe.” Granted, Murray must not have completely hated the role, because in 2006 the sequel to the Garfield movie was released and, you guessed it, Bill Murray was back to voice the role. Despite its poor critical reception, “Garfield the Movie” made over 200 million dollars worldwide.
5 Benedict Cumberbatch regrets not yet having children
Benedict Cumberbatch, the actor who stars in the British series “Sherlock,” has a vast fanbase online. Despite his wide appeal to both fans and filmmakers, the actor (who is in his late 30s) has spoken publicly about his numerous insecurities, including telling the British paper the Daily Mail that his regret is that he hasn’t had children yet. He’s also still unmarried, which has provided fodder for tabloids (and his fans) over the years. He is especially elusive about his personal life, though he’s been linked with several high-profile women such as Liv Tyler and a British actress.
4 Justin Timberlake regrets not supporting Janet Jackson
Singer, songwriter and performer extraordinaire Justin Timberlake experienced one of the most memorable moments in his career at the 2004 Super Bowl half-time show, when he was performing with Janet Jackson. At the end of their song, Timberlake ripped open her jacket and revealed her naked breast, which soon became dubbed a “Wardrobe Malfunction” and the controversy was called “Nipplegate.” A few years later, Timberlake admitted in an interview with Entertainment Weekly that he regretted how he handled the incident, stating that Jackson took much of the blame and he should have been more supportive of Janet during that time.
3 Matt Damon and “The Bourne Ultimatum”
Although the “Bourne” franchise of movies has made over a billion dollars worldwide, its star Matt Damon has actually spoken out against the franchise and in particular his role in the third movie, “The Bourne Ultimatum.” He once told GQ that the script for the movie, penned by Tony Gilroy, was bad and accused it of being a “career-ender.” However, those comments also turned into a cause for regret for Damon: he later called the publication back and said his comments were stupid and unprofessional. He has since explained (in more tactful terms) why he chose to be absent from the subsequent film, 2012’s “The Bourne Legacy”: he believes that the storyline for his character has run its course.
2 Cher regrets (missed) sexual conquests, Burlesque, and anti-Miley tweets
Cher has had a career that has spanned decades, and as a larger-than-life singer and Oscar-winning actor known for her imaginative costumes, she's also spent a lot of time in Hollywood and rubbed elbows with many iconic stars. In interviews, Cher has admitted to many things, including regretting the movie "Burlesque," that she starred in with Christina Aguilera. More recently, she dissed Miley Cyrus over Twitter following the young singer's infamous 2013 VMA performance, though later said it was a mistake to speak out against Cyrus. Cher has also discussed her Hollywood conquests (and almost-conquests) over the years, saying that she regrets not spending more time in her affair with Marlon Brando and also regrets turning down Elvis Presley, who once invited her over to his house.
1 Katherine Heigl regrets “Knocked Up”
Actress Katherine Heigl almost immediately spoke out against the 2007 comedy “Knocked Up” after it wrapped. She blasted the movie, which also starred Seth Rogen and Paul Rudd, for being sexist because it portrayed men as fun-loving and loveable, but she didn’t like how it portrayed women as being uptight. She said that she had a very hard time playing her character, especially since the men were funny and her character wasn’t.
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