15 Celebs Who Are Ashamed Of Their Past (And 5 Who Are Proud Of It)

Celebrities are not known for making the best choices in life but there are some who take their mistakes in stride and some who live in shame. You know those nights when you're lying in bed and you can't sleep because your mind is running wild thinking about all of the embarrassing things you did ten years ago? Well celebrities can have the same problem but it's much worse for them since most of their biggest mistakes and embarrassing moments were captured in photos and videos.

For some celebrities, their biggest regrets were unfortunate movie roles, messy divorces, cheating scandals, appearing in their own reality TV show, posing naked for magazines, and going too far with plastic surgery. You'll never believe which famous diva says she regrets not hooking up with two Hollywood icons. If we were her, we'd regret it too!

There are also some celebrities who have made mistakes or done embarrassing things but they claim that they have no regrets. They inspire us to come to terms with our mistakes and to learn from them instead of dwell on them. Unfortunately for them, some of their mistakes were a lot worse than the time we accidentally called our teacher "mom."

These celebs have either made shameful and embarrassing mistakes or just some bad choices that seemed the right choice at the time. Which ones regret their pasts and which ones don't?

20 Ashamed: Robin Thicke And His Blurred Lies

After Robin Thicke made a fool out himself at the 2013 VMAs, was caught grabbing a woman's behind at a nightclub, and was rumored to be cheating, his wife Paula Patton decided enough was enough and she dumped him. In response, Thicke released an album titled Paula in an attempt to win her back. It didn't work. The album is basically just a whiny mess of songs in which Thicke begs his ex-wife to forgive him and apologizes for the mistakes he made. Since the album was a total flop, he seems to regret ever releasing it in the first place. Now he's got a young new girlfriend, April Love Geary, who is almost 20 years younger than him, and a baby on the way. He says now he doesn't have any regrets but his terrible album provides plenty of receipts that show that he's not being completely honest with us or himself.

19 Ashamed: Kris Kardashian to Jenner

The best decision Kris Jenner ever made in her life was to hook up with Robert Kardashian and have three daughters with him--she probably regrets having Rob though. Her daughter Kim has helped to make her wildly rich and Khloe and Kourtney help bring in the dough as well. However, before Kardashian passed away, he and Kris got divorced and she later remarried. She says now that she regrets ever divorcing her husband (and she undoubtedly regrets changing her famous last name). In an interview she admitted, "The one regret, if I had to do it over, would be divorcing Robert Kardashian. But then there wouldn't have been Kendall and Kylie, so that's the way I look at that." Of course she would regret having her rich and famous daughters who have a successful modeling career and a million dollar cosmetics company between them.

18 Ashamed: Britney Spears' Career Move Was Toxic

Unfortunately for Britney Spears, her list of bad choices is a long one and there are a lot of mistakes she's made that she could regret. However, she claims that there is only one thing that she regrets and it was the worst thing she'd ever done. No it wasn't the time she almost dropped her baby headfirst on the sidewalk. It wasn't the time she shaved her head. It wasn't even the time she attacked a paparazzo with an umbrella. What she regrets most of all is her reality show with her ex Kevin Federline: Britney & Kevin: Chaotic. Looking back on it, she said, "I would never do something like that again. Actually, that was really bad. That was probably the worst thing I've done in my career.” To be fair, the reality show nearly killed her career and Flak Magazine called it an "insult to common sense and decency". Yeah, if you're going to regret something, a tacky reality show is probably the way to go.

17 Ashamed: George Clooney Was A Very Bad Batman

Before George Clooney became the big star he is today, he was everyone's least favorite Batman--at least before Ben Affleck suited up. Looking back on it, Clooney revealed that he regrets the role and the movie, Batman & Robin, as a whole because it was made "solely for commercial reasons." He also revealed that he kept a photo of himself as Batman in his office as a cautionary reminder. While he definitely regrets playing the caped crusader, at least he is a good sport about it. “With hindsight it's easy to look back at this and go, 'Woah, that was really s**t and I was really bad in it. It was a difficult film to be good in.” He realized that after that train wreck of a movie, he needed to pick and choose his projects more carefully. His next three movies following Batman & Robin were Out Of Sight, Three Kings, and O Brother, Where Art Thou?

16 Ashamed: Nicole Kidman's Marriage Was Regrettable

After all of the strange stories that have come out about Tom Cruise in the past two decades, it's not hard to believe that his ex-wife Nicole Kidman regrets ever being married to him in the first place. She said: "I was so young when I got married [to Tom Cruise]. I look back now and I'm like, 'What?' You look at Taylor Swift, I mean how old is she? She's 26. I had two kids by the time I was 27 and I'd been married for four years. But that's what I wanted." Kidman also revealed that the end of her marriage caused her to be the "loneliest" she'd ever been but it led to something much better--her relationship with husband Keith Urban and their two daughters, Sunday and Faith. Unfortunately, she is estranged from her two adopted children allegedly because of their involvement in Scientology which is something she probably regrets as well.

15 Ashamed: Pamela Anderson Is The Ghost of Playboy Past

According to Pamela Anderson, posing nude for Playboy didn't exactly help her two kids make friends in school. Despite having posed naked for a photoshoot just a month before, she said in an interview that her nude photos caused her sons to be bullied in school and that she regretted "anything I have ever done has made them uncomfortable or suffer." Anderson said that her two sons were "made fun of because I have posed naked. When you pose, you are not thinking that one day you will have children who will see it." Of course, this hasn't stopped her from posing naked for other magazines since then so we don't know exactly how much she regrets her nude photoshoots in the past. Her two sons, Brandon and Dylan are both adults now so hopefully they don't have any trouble with bullies anymore.

14 Ashamed: Kim Kardashian, Her Only Regret Is a Manicure

Most of the regret-worthy things that Kim Kardashian has done has actually helped her career to thrive including her 72-day marriage, her endless nude selfies, and her infamous x-rated tape which actually made her a celebrity in the first place. She's done a lot of things that would embarrass most of us but she doesn't seem to have any regrets because it all helped her to get to where she is today. The one thing that she said she regrets the most is one you wouldn't expect. When Kim got engaged to now-husband Kanye West, she posted a photo on Instagram of the ring and she hated her manicure: “One of my biggest photo regrets is when I got engaged, I had the shortest nails when I showed my picture. And I was like, 'Ugh, it would have looked so much better with long nails.'” Truly iconic.

13 Ashamed: Angelina Jolie's Bad Santa/Bad Husband

Back when Angelina Jolie was one of the hottest actresses in the world, she hooked up with one star that no one expected: Billy Bob Thornton. The two were always considered an odd pairing since he was 20 years older than her and wasn't exactly Hollywood's hottest star. According to the Bad Santa star, he regretted that he los Jolie because of his insecurity and inability to compromise: “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.” The couple split in 2003 and by 2004, Jolie was romantically linked to her Mr. and Mrs. Smith costar, Brad Pitt, which seemed like a more suitable pairing… besides the fact that he was married at the time.

12 Ashamed: Heidi Montag And Her 10 Surgeries in One Day

It's hard to believe that it's been almost eight years since The Hills came to an end! Back in 2010, Heidi Montag was a huge celebrity thanks to her infamous pairing with the villainous Spencer Pratt. So what did she do with all of the money she made from the show? She got 10 plastic surgeries done in a single day. Though it was what she wanted at the time, Montag now says that she regrets being so obsessed with how she looked and spending all of her money on surgeries that only stunted her career. In an interview, she said, "Surgery ruined my career and my personal life and just brought a lot of negativity into my world. I wish I could jump into a time machine and take it all back." Surprisingly, she and Pratt are still together and she recently gave birth their first child, a boy named Gunner.

11 Ashamed: Kelly Osbourne Was Born to Be Wild

We have all done things that we regret, especially as a teenager but imagine how much worse it would be if you spent your entire life in the public eye! Kelly Osbourne, daughter of Ozzy and Sharon Osbourne, has said that she regrets many things from her past such dating various ex-boyfriends, doing drugs, collecting some bad tattoos, and a getting some atrocious haircuts. However, she said that the thing she regrets the most is hurting her mom and dad. She said in an interview, “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.”

10 Ashamed: Miley Cyrus The Wrecking Ball Music Video May Wreck Her Career

Miley Cyrus was one of the many stars who went through the transition of Disney child star to adult star and she chose a pretty crazy way to do it. First she chopped off her hair and dyed it platinum blonde, started wearing a lot less clothes, and twerked with a giant foam finger at the VMA's in 2013. Looking back at it all, Cyrus said that the thing she regrets the most is swinging around naked on a wrecking ball in her music video for "Wrecking Ball". "Swinging around naked on a wrecking ball lives forever," she said in an interview. "I'm never living that down. I will always be the naked girl on a wrecking ball… My worst nightmare is that being played at my funeral." Recently Cyrus has completely changed her image from the twerking, weed-smoking, scantily clad pop star to a more down-to-earth singer songwriter.

9 Ashamed: Ellie Goulding Is My Fair Lady

Now this is one regret that few of us can relate to! Pop star Ellie Goulding grew up in Hereford, England and she was so embarrassed about her accent that she decided to pull an Eliza Doolittle and completely change her accent. Goulding described her former accent as"quite Bristolian" and she studied British TV newsreader Nicholas Witchell in order to adopt his posh, sophisticated accent so that she could be taken seriously in the business. By the time she had become a famous musician, she had been using the accent for years and it was too late to start using her old accent again. “I became fixated on speaking well," she said. "I felt like people just knew I was from a council house and that I was poor because of the way I spoke." “I feel silly because I'm not ashamed of the Hereford accent now and it's too late to get it back.”

8 Ashamed: Courtney Cox And Her Excessive Botox

You might wonder what the deal is with women's obsession with plastic surgery in Hollywood and there is a pretty simple explanation. According to Hollywood's standards, a woman is past her prime by the time she has reached the ripe old age of 30 which causes the female stars to do whatever they can to hang on to their youth. Courteney Cox says that she regrets succumbing to the pressure that Hollywood puts on women. "I think there's a pressure to maintain [your looks] not just because of fame, but just being a woman in this business," the Friends star said. "I have done things that I regret and luckily there are things that dissolve and go away. So that's good because it's not always been my best look." It's sad how Hollywood can make talented and beautiful female stars feel like they're past their prime while male stars can star in big-budget movies well into their 50s and 60s.

7 Ashamed: John Mayer Should Have Bit His Tongue

John Mayer has said a lot of things over the years that he now regrets. The most memorable of his poorly chosen words was when he referred to his manhood as a "white supremacist" or when he called his ex-girlfriend Jessica Simpson a "drug" in the bedroom, also adding that "drugs aren't good for you if you do lots of them." Oh and let's not forget the time he bad-mouthed his ex Jennifer Aniston saying that the reason they broke up was because she was "still hoping it goes back to 1998." According to Mayer, he only said those tings because he had nothing else to say. "I was going through a time in my life where I didn't really want to share what was going on, but I didn't want to be boring," Mayer said. "When you're just open, but not honest, then you start free-associating garbage. It doesn't mean I can go back and scrub it out, but I understand it now.”

6 Ashamed: Cher, If She Could Turn Back Time…

Cher has been the Goddess of Pop for decades and, over the years, she's managed to hook up with some of the hottest stars of their day including Warren Beatty, Val Kilmer, and Tom Cruise. However, even though she's still hugely successful with an Emmy, an Oscar, and a Grammy under her belt, she still has two regrets: not hooking up with Marlon Brando or Elvis when she had the chance. In an interview with David Letterman, she was asked if she had hooked up with Elvis and she said that she almost did: "I got nervous," she said. "I didn't get there (to the date), I was that nervous. I wish I had." She then said that she also missed an opportunity to hook up with Marlon Brando: "I wished I had!" she said speaking of The Godfather star. "We just hung out for a while, but I wished I'd had." Still, being able to hang out with Brando and Elvis is still pretty amazing.

5 Proud: Dolly Parton, No Kids, No Regrets

There are a lot of people out there who think that women who never have children regret it but that is just not the case. Dolly Parton is one of the most successful singers of all time and she said that she doesn't regret focusing on her career and giving up on her chance to have a family. According to Parton, she believed that she was supposed to regret not having children but she realized that she didn't, saying: "Early on, when my husband and I were dating, and then when we got married, we just assumed we would have kids. We weren't doing anything to stop it. In fact, we thought maybe we would. We even had names if we did, but it didn't turn out that way. Now I say, 'God didn't mean for me to have kids so everybody's kids could be mine.'" Well said, Dolly!

4 Proud: All About Bette

Bette Davis was one of the fiercest Hollywood starlets of all time and she lived her life free of regrets--even though she was known for being a bit of a diva. Though she famously rivaled with fellow actress Joan Crawford, she also made many more enemies during her time in Hollywood and it was that tenacity that helped to solidify her as a fixture of classic Hollywood film. When it came to her career, Davis said it best: “I do not regret one professional enemy I have made. Any actor who doesn't dare to make an enemy should get out of the business. I worked for my career and I'll protect it as I would my children - every inch of the way. I do not regret the dust I've kicked up. I always fought people my own size and more often than not they were bigger.” Basically, she didn't let the haters get her down.

3 Proud: Selena Gomez, Either She Has No Regrets Or She's a Bad Liar

Selena Gomez and Justin Bieber had a rocky relationship which consisted of a lot of breakups and makeups and as much as we might wish that they would quit each other for good, they got back together in 2017. Sure, they're a cute couple but their relationship is a turbulent one and we just want the best for Selena! However, even before the two got back together, the former Disney star said that she didn't regret their relationship one bit: “It was really weird but it was incredible. I would never take it back in a million years. You live and you learn, you know?” Apparently she didn't learn much because she hooked up with the "Love Yourself" singer almost as soon as Gomez broke up with The Weeknd. We're glad that the Spring Breakers star is happy but hopefully she won't do anything this time that she'll later regret!

2 Proud: Reese Witherspoon Can Be Cruel to Be Kind

It might be easy to regret being in a relationship with someone who cheated on you but Reese Witherspoon claims that she doesn't have any regrets. Witherspoon married her Cruel Intentions costar Ryan Phillippe in 1999 but they broke up in 2007 after he cheated on his wife with his Stop Loss costar, Abbie Cornish--something which Phillippe probably regrets because his career tanked as soon as the rumors of his affair started circling. However, Witherspoon said she wouldn't take any of it back. "It's about that next chapter in your life," she said. "What do you do when you get to 40 and you made a decision when you were 25 to get married and have kids? I got married when I was 23 and had two kids by 27… Sometimes it's good to know yourself. I would never change anything!"

1 Proud: 2018 is the Year of Amanda

You might think that if anyone has any regrets, it would be Amanda Bynes who was once a talented, up-and-coming star who lost everything as she struggled with mental illness and addiction. While Bynes was the subject of criticism and cruel jokes for years, she has been doing her best to get healthy and to stay optimistic. In 2011 she said, “I believe in no regrets. You say what you feel because you felt it at the moment… I really just needed some time off. I've been acting since I was seven… So, it's not retiring so much. It's just taking some time off." While she has been in and out of rehab for the past several years, she gave her first interview in four years in 2017 looking happy and healthy. She said that she's sober and she's ready to start acting again. Let's hope that 2018 is the year of Amanda Bynes' comeback!