It is often said that what you regret most at the end of your life are the things you didn’t do. However, the celebrities in this gallery may disagree. Despite the fact that they seem to have reached their goals and made all the right choices, even they struggle with regrets. These regrets range from the unfortunate, to the ridiculous, to the truly heartbreaking. Curious? Click on and discover your favorite celebrities’ biggest personal regrets.
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Britney Spears
There’s no shortage of things that come to mind when mentioning regret and Spears‘ name in the same sentence, though her own reply to the question might surprise some.
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Britney Spears
She considers her ill-fated reality show with ex Kevin Federline, ‘Britney & Kevin: Chaotic,’ to be her biggest regret. In her own words: “I would never do something like that again. Actually, that was really bad.”
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Kim Kardashian
Surprisingly, one of the socialite’s biggest regrets came on the day that she became engaged to Kanye West.
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Kim Kardashian
She has said that her biggest photo regret is when she got engaged and showed off the ring with short nails instead of long ones. Well, she seems to have her priorities straight!
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Oprah Winfrey
She’s one of the most famous women in the world, with a list of accomplishments that’s seemingly endless. Though they’re few, she still has some regrets.
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Oprah Winfrey
According to the billionaire philanthropist, “the hardest part is really recognizing the time that you’ve wasted and the things that you worried about that really didn’t matter. You regret the time that was wasted.” A piece of advice we can all relate to.
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Kanye West
The rapper stated that he really regretted not having more nudity in his famous ‘Bound 2’ video, featuring Kim Kardashian.
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Kanye West
In an interview with GQ magazine he commented, “I would have just liked to have had more nudity in it. That’s the only thing. I just want to do crazy, colorful s*** like that that has more nudity.”
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Cher
With an Emmy, an Oscar, and a Grammy under her belt, Cher is one of the most successful people working in show business today.
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Cher
Her regrets? Dating! At different times in her career she had the chance to date Marlon Brando and Elvis Presley. So, why didn’t she? With Elvis she “got nervous.” On Brando she commented “We just hung out for a while, but I wished I had.”
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Jennifer Garner
She regrets her marriage to her first husband, Scott Foley, whom she married when she was in her 20s. She thinks it was too early.
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Jennifer Garner
“I wish I’d known to wait for marriage until I was 30 or over,” she confessed about the two-and-a-half-year marriage.
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Charlie Sheen
Charlie Sheen is another celebrity who’s probably not lacking in regrets. But one of his biggest is actually pretty selfless.
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Charlie Sheen
He regrets calling his former ‘Two and a Half Men’ co-star Jon Cryer a “traitor” for not getting in touch with him after he left the show. He stated, “That was wrong. I whaled on him unnecessarily.”
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Nicole Kidman
Even though it’s been almost two decades since she divorced Tom Cruise, the Australian actress still considers her marriage to the actor deeply regrettable.
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Nicole Kidman
“I was so young when I got married […]. I look back now and I’m like, ‘What?'” Thankfully these days she’s happily married to singer Keith Urban.
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Tom Cruise
What does the Hollywood actor regret most? No, it’s not marrying Nicole Kidman. It was criticism he made in the media on Brooke Shields’ alleged use of drugs to treat her postpartum depression.
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Tom Cruise
However a year later the actor repented, saying, “it came out wrong, it’s just not true. I was raised by four women who have children and babies. I’m not trying to tell anyone how to live their life or what they should believe or shouldn’t believe. I felt I could have handled it better.”
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Justin Timberlake
This one’s a little more serious. The singer says he still has regrets about what happened during his now infamous 2004 Super Bowl halftime show with Janet Jackson, otherwise known as “Nipple Gate.”
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Justin Timberlake
Justin says he regrets not supporting Janet more after the media storm that followed the wardrobe malfunction live on air.
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Billy Bob Thornton
Billy Bob’s regret stems back to the time he was married to Angelina Jolie. Not only was he 20 years her senior, he was also very insecure, especially when her career started to take off.
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Billy Bob Thornton
According to the actor, “we had a great marriage and I chickened out because I didn’t feel good enough.” Ouch!
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Nick Lachey
The 98 Degrees singer has similar regrets to Britney Spears. But whereas Britney’s reality show was mercifully short-lived, ‘Newlyweds: Nick & Jessica’ ran for three whole seasons.
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Nick Lachey
It aired from 2002 until 2005, roughly the duration of their marriage. What does he think of it now? Well, he called it “among the dumber ideas I think I’ve ever seen executed in history.”
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Kelly Osbourne
Being a teenager is hard enough, but imagine having to spend most of your teenage years in the public eye. That’s what happened to Kelly Osbourne, and she has a list of regrets to boot.
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Kelly Osbourne
In hindsight she says she “did a lot of really, really stupid things and it was because it was my way of crying for help […] being disrespectful to my mother, which to me is one of my biggest resentments because I love my mum; my mum’s my best friend. I hate the fact that I hurt her and my father.”
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Kenny Rogers
The country singer’s biggest regret according to HuffPost is having to miss out on time with his family during his career. The 81-year-old seems to have learned from his mistakes however.
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Kenny Rogers
He said “my bucket list now concerns my kids. There are things I’d like to do with them so I’m putting work on the back burner for a while and really making them my priority.”
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Usher
Usher’s biggest regret is not spending more time with his dad before he passed away.
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Usher
“Instead of being there when he was sick, I was working. No amount of money could have fixed my father’s health, but I could have just spent that time with him.”
