The biggest regrets of your favorite celebrities

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."

Want to find out more? Check out celebrities' biggest relationship regrets!

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The biggest regrets of your favorite celebrities

Some regrets are bigger than others

09/10/19 | StarsInsider

CELEBRITY Regret

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.