28 Huge Celebrities Living With Major Regrets

Howard Stern regrets dunking on Robin Williams GRACKED.COM Stern says he blew it when he interviewed Williams in the 90s. Instead of letting Robin be Robin, Howie felt like he needed to dredge up some controversy to keep his listeners entertained: "there I am beating him over the head with, like, 'Hey, I hear you're f*ing your nanny?"

We probably all have a little something in our past that we’d like to take back. Right? Right, you guys? If not, good for you. We regret spending over $200k on that “Bachelor’s of Pre-List Blurb Writing” degree, when it wasn’t even a prerequisite to get this job! They’ll let any old fact-loving dope off the street these days, and at this rate, we won’t pay that loan off for decades!

After making our most recent loan payment, we scoured the site for celebrities, comedians, and prominent figures who’d like a mulligan on a certain decision they made back in the day. It’s comforting be around other regret-havers. Man, there must be a better term for that.

28.

Howard Stern regrets dunking on Robin Williams GRACKED.COM Stern says he blew it when he interviewed Williams in the 90s. Instead of letting Robin be Robin, Howie felt like he needed to dredge up some controversy to keep his listeners entertained: "there I am beating him over the head with, like, 'Hey, I hear you're f*ing your nanny?"

27.

Jennifer Aniston regrets that haircut CRACKED.COM Her signature proto-Karen haircut made her a sex symbol in the 90s, but Aniston now says "the Rachel" is "the ugliest haircut I've ever seen."

26.

Justin Timberlake regrets not taking responsibility CRACKED.COM After perpetrating the blatantly (and lamely) choreographed 2004 Super Bowl "wardrobe malfunction," JT bravely claimed he "could've handled it better." Не totally would have taken some of the heat! Alas, the problem is systemic: "I probably got 10 percent of the blame, and that says something about society."

25.

Paul McCartney regrets his $27 million marriage CRACKED.COM On one hand, he had to shell out millions of dollars to dissolve his marriage to Heather Mills. But on the other hand, "I tend to look at the positive side, which is that I have another beautiful daughter out of it."

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24.

Huey Lewis wishes he'd sold out CRACKED.COM After Michael Jackson's landmark Pepsi deal, Coke wanted to throw a few million dollars at Huey to use "The Heart of Rock & Roll." Не turned them down, a move he now calls "stupid."

23.

Nick Lachey regrets his first attempt at reality TV ARQU STARSY CRACKED.COM Не calls his first foray into the genre, Newlyweds: Nick and Jessica, "among the dumber ideas I think I've ever seen executed in history."

22.

Kendrick Lamar wishes he'd gone to college CRACKED.COM Не says he's too deep into his career to carve out time for higher ed at this point, but "Not experiencing college, at least for a semester, that was my biggest regret."

21.

Britney Spears regrets getting into reality TV CRACKED.COM Marrying Kevin Federline in the first place was kind of a bad idea. But it was making Britney and Kevin: Chaotic that was "probably the worst thing I've done in my career."

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20.

Miley Cyrus is over "Wrecking Ball" CRACKED.COM Playing a game of Marry Kill with her own songs, she opted to kill "Wrecking Ball:" "I will always be on a wrecking ball... My worst nightmare is that being played at my funeral."

19.

Sophie Turner wishes she'd gotten wasted G! TUD CRACKED.COM Having done Game of Thrones throughout her formative years, she's bummed to have missed out on the whole college thing. Or, as she put it, she wishes she'd "gone out and drunk a lot and thrown up in the middle of a club without it being photographed."

18.

28 Huge Celebrities Living With Major Regrets

17.

CRACKED JIMMY FALLON apologized for doing blackface on SNL. In 2020, he said, "In 2000, while on SNL, I made a terrible decision to do an impersonation of Chris Rock while in blackface. There is no excuse for this. I am very sorry for making this unquestionably offensive decision and thank all of you for holding me accountable."

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16.

NIKKI GLASER apologizes for body-shaming Taylor Swift. After calling her "too skinny," and saying her body "bothers" her, she said, "That should be used as an example of 'projection' in PSYCH101 textbooks. I talk openly about battling some kind of eating disorder for the past 17 years. I was probably 'feeling fat' that day and was jealous." CRACKED

15.

CRACKED TINA FEY pulled 30 Rock' S blackface episodes from circulation. About the four episodes, she said, "I understand now that 'intent' is not a free pass for white people to use these images. I apologize for the pain they have caused. Going forward, no comedy-loving kid needs to stumble on these tropes and be stung by their ugliness."

14.

CHUCK LORRE apologized for Two and a Half Men during an acceptance speech. After winning a Television Academy Honors award for Mom in 2014, Lorre said, "To do a show about people trying to redeem their lives and to salvage and repair the damage they've done, for me, it's an opportunity to apologize for Two and a Half Men." CRACKED.COM

13.

CRACKED "WEIRD AL" YANKOVIC regrets using the word "midget." "These days, I do not say that word. In fact, at one point on tour, I sang the song that had that word in it and I stopped the whole band and just explained to the audience how language has evolved over time, and I wouldn't use the word now. And then we resumed playing."

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12.

COMEDY NERD Trevor Noah thinks the old tweets that got him in trouble were... stupid. The way he put it is that the slightly younger Noah who'd written those Twitter jokes way back when was actually just being idiotic. CRACKED.COM

11.

COMEDY NERD David Letterman publicly said he felt bad about making fun of Monica Lewinsky. It happened in 2014, after he'd read an essay in Vanity Fair in which she wrote about how humiliated she'd been by the whole scandal. CRACKED.COM

10.

COMEDY NERD Gilbert Gottfried made some tasteless jokes about Japan, then apologized. N GAL Не made them after an earthquake and tsunami in Japan - and his apology came too late to prevent Aflac from dropping him as spokesman. CRACKED.COM

9.

COMEDY NERD Seth MacFarlane says Family Guy wouldn't do the JFK Pez Dispenser joke today. Here's the joke: A kid gets the head of his new John F. Kennedy Pez Dispenser blown off, then says "Good thing I still have my Bobby Kennedy Pez Dispenser." CRACKED.COM

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8.

Emma Stone apologized, loudly, during the Golden Globes CRACKED.COM Emma Stone took a lot of flack after taking the role of a part-Chinese woman in 2015's Aloha. Sandra Oh brought it up again at the 2019 Golden Globes, and Stone can be heard yelling "I'm sorry!"

7.

COMEDY NERD Conan O'Brien publicly regretted making an offhand joke about Anne Frank. At one point in a documentary about him, when they tell him his tour will be over soon, he says "That's what they said to Anne Frank." CRACKED.COM

6.

Tom Hanks regrets giving himself diabetes CRACKED.COM Hanx says he has no one to blame but himself for his type 2 diabetes diagnosis: "I'm part of the lazy American generation that has blindly kept dancing through the party and now finds ourselves with a malady."

5.

Burt Reynolds regrets making the movie that earned him an Academy Award nomination. Reynolds hated making Boogie Nights with the then 26-year-old Paul Thomas Anderson, who the actor described as "young and full of himself." Не even turned down the director's next film, Magnolia. CRACKED.COM

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4.

Stephen King really regrets directing Maximum Overdrive, which he calls a "moron movie". hn F. Kenned 77 Maximum Overdrive star Emilio Estevez says, "The few times that I've connected with him over the years, he's like, "Can you forgive me for that?" CRACKED.COM

3.

CRACKED GO RTUNY ORT RTU WARREN BUFFETT Warren Buffett's rise to success with Berkshire Hathaway was not without its mistakes; he regrets not tendering his shares when Seabury Stanton tried to buy them back at a lower price, and he also regrets buying Berkshire's stock at a high price and combining National Indemnity Company with Berkshire Hathaway, which cost him an estimated $100 billion.

2.

Daniel Radcliffe strongly regrets the way he played Harry in the sixth film. Radcliffe outright hates Harry Potter and the Half-Blood Prince. Не tried to portray Harry as emotionally shut off due to trauma, but that made for a really dull performance, he says. To him, watching it was watching "a mistake you made every day for 11 months." CRACKED.COM

1.

Alison Brie regrets voicing a Vietnamese-American on Bojack Horseman. "In hindsight, I wish that I didn't voice the character of Diane Nguyen," she said. Her thinking at the time was that "the world of animation" is different. CRACKED.COM

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