These celebrities would have.
They probably could have.
And they really wish they could have.
Below, we present a rundown of regrettable actions these stars continue to live with today…
Sorry, Ms. Janet
Justin Timberlake apologized back in the day for his role in Nipplegate at halftime of the 2004 Super Bowl. Years later, though, he told Entertainment Weekly that he regretted letting Janet Jackson take so much of the blame: “I wish I had supported Janet more. I am not sorry I apologized, but I wish I had been there more for Janet.”
Way Too Chaotic
Britney Spears has said her biggest regret was agreeing to participate in Britney and Kevin: Chaotic, the reality program that profiled her controversial relationship with ex-husband Kevin Federline back in 2005. We don’t blame her.
Not a Honeymoon
Nick Lachey can relate to Britnsy Spears. He says that doing Newlyweds with then-wife Jessica Simpson was “among the dumber ideas I think I’ve ever seen executed in history.”
Batman & Robin & My Bad!
George Clooney has a sparkling resume. But he’s on record as saying he totally messed up his role in 1997’s Batman & Robin.
Missing Mom
Kanye West doesn’t regret much he has ever said or done. But he wishes more than anything that his mother could have met her granddaughter, North.
The One That Got Away
Billy Bob Thornton had Angelia Jolie. He had her! And then… “I was just too insecure… people actually said that I didn’t deserve to be with her…when Angie and I got married, during that time, I was more famous than she was to start with and then she becomes this big thing; it’s hard in these relationships. We had a great marriage and I chickened out because I didn’t feel good enough.”
Cher and Cher Alike
Cher has said her biggest bedroom regret centers around two iconic stars: she had the chance to date Marlon Brando and Elvis Presley and turned down both opportunities.
All Grown Up
Kelly Osbourne is now, at least. But this is what she has said about her past: “I did a lot of really, really stupid things and it was because it was my way of crying for help… going out and staying out all night, and 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.”
Not Winning
Charlie Sheen doesn’t think he was ever losing during his rants against Chuck Lorre. But he wishes he nver brought ex-co-star Jon Cryer into the picture, saying: “That was wrong. I whaled on him unnecessarily… he just got caught in the crossfire. He’s a beautiful man and a fabulous dude and I miss him.”
What a Disick!
Think Scott Disick wishes he had not been disloyal to Kourtney Kardashian? After their split, he Instagrammed this picture of a place card that at one time would have read “Scott Disick and Kourtney Kardashian.” He followed it up with this caption: “When u realize the grass isn’t always greener.”
Death is Forever
This one is rather serious: Juicy J says his biggest regret is not speaking up about his friend Pimp C’s codeine addiction before he died in 2007. “My biggest regret as an artist was not telling Pimp C to slow down,” J has said. “I don’t have any regrets as far as my own personal career goes, everything that happened, happened for a reason, but the death of Chad changed my life forever.”
Bad Career Move
Mase went from being a rapper to being a pastor. How does he feel about that decision? “I didn’t give myself any room to grow, I went from one extreme to another extreme, I was just so gung ho about what I was learning, that’s all I wanted. I went so hard in one direction that people had things to say and rightfully so. I don’t blame them for that [but] it’s been 13 years, let’s move on.”
A Bad Rap
Rick Ross said rapping nonchalantly about date rape in the past was one of his biggest regrets as “a father, a son, and a brother to some of the most cherished women in the world.” The guy also may have committed some murders, but he hasn’t talked openly about those.
The Big O
This one is a little vague, but it’s Oprah. She’s said she regrets wasting time in the past on things that didn’t really matter.