From questionable fashion choices to the actions that landed you in detention, there are hundreds of things that we all wish we hadn't done when we were younger — and things that we might have done differently if we knew we'd have to explain them to our kids someday. That's why hindsight is 20/20, of course, and we imagine that's even more true for celebrity moms. After all, the scrutiny for their decisions — both past and present — is high, and every mistake they make is broadcast for the world to see. The mistakes of their youth basically never go away.
This means that the evidence of their wild days is easily discovered by their children, especially if it was ever on social media. (Instagram is forever!) And through the years, stars including Drew Barrymore and Gwyneth Paltrow have come clean about what their teen years and 20s were like before they became moms (and what they might do differently today).
We've rounded up some celeb moms who had a bit of a wild streak when they were younger (and, for some, in the not-so-distant past). Still, despite the headlines they've made, they're some of the best Hollywood moms around — and many of them haven't been afraid to own up to their wild pasts, even when it means discussing topics with their kids that they probably would have rather avoided.
Kim Kardashian
Kim Kardashian is no stranger to making headlines with her romantic life. Her marriage to Kanye West ultimately didn't work out, but their relationship did signify an end to Kim's search for love in many different places before she settled down and had four kids. Remember when she eloped at 19 and married music producer Damon Thomas?
And, of course, no one will ever forget that infamous sex tape, featuring Kim and singer Ray J, which was leaked and still haunts her today. We even saw a scare on The Kardashians not so long ago when Kim thought that her kids finally found out the truth, but it seems like she's managed to buy herself a little time before she has to explain that one — at least for now.
Christina Aguilera
Former Mouseketeer Christina Aguilera broke the Disney mold in a big way. In 2002, she declared independence with her album Stripped. And the one-time Voice coach made it clear that she was doing things her way, as she released the signature single "Dirty," which ditched the teeny-bopper vibe and explored her sexuality more than ever. Xtina was born — and since then, so were her kids, Summer and Max.
Reese Witherspoon
No one likes seeing the flashing lights of a police cruiser, especially if they're pulling up alongside you. Well, the same goes for Reese Witherspoon, who was arrested in 2013 for disorderly conduct. And the star, who was already a mom of three at the time, had plenty of interesting things to say despite being told to stay in the vehicle. Reese, who apologized for her out-of-character behavior, told Good Morning America, "I saw him arresting my husband and I literally panicked. I said all kinds of crazy things."
Jenelle Evans
Teen Mom 2 star Jenelle Evans has had her fair share of trouble. After all, we've seen it play out on MTV for years (remember that epic brawl caught on camera in 2011?). Aside from fighting, this mama has a history of partying and being arrested for possession of drugs — and assaulting her then-husband Courtland Rogers.
But Jenelle is trying to turn it around, and seems like a much calmer mom these days to Jace, Kaiser, and Ensley.
Pink
Who doesn't remember when Pink stepped onto the scene with her signature hair and soulful voice? But no one can forget that rebellious attitude that she's known for (yes, the one that had her calling out everyone from pop stars to presidents — "Dear Mr. President," anyone?).
The "So What" singer even once admitted to People: "I was a delinquent. An angry, rebellious, self-righteous, ambitious, crazy person who liked to have too much fun." And in the past, she's spoken about her issues with drugs — having overdosed once — and even selling them.
She's mellowed a bit since becoming a mom to daughter Willow and son Jameson, but there's no doubt she's still the outspoken artist that we absolutely love.
Nicole Richie
Nicole Richie was known for her party-girl ways right along with bestie Paris Hilton. (As if we could ever forget that the two took their antics public in their reality show The Simple Life.) This mom had some crazy times like getting arrested for heroin possession, all before turning 22.
But it seems those days are in the past, and Nicole now makes no apologies for her wild-child past, which she made clear in an essay for Lenny Letter in 2016.
Fergie
Fergie may have the sweet life now, as she's topped the charts and become a mom to son Axl with ex Josh Duhamel, but she didn't always. This child actress-turned-singer revealed to Rolling Stone that she got caught up in the club scene and battled addiction for a time before eventually linking up with the Black Eyed Peas.
Nicole 'Snooki' Polizzi
Most of the world has seen Nicole "Snooki" Polizzi's days of partying, drinking, and drama-filled fights with friends play out on the MTV hit Jersey Shore. Then, there was Snooki & Jwoww, where she and pal Jenni "Jwoww" Farley took on the town. But nowadays, Snooki is living the married life and is a mom of three, so she's got less time to party at the shore.
Drew Barrymore
Drew Barrymore got her start as a child actor, and like many others, she learned that having fame at a young age is hard. The host of the Drew Barrymore Show got candid in an older interview with People, even revealing that she had her first cigarette at 9. She went on to describe a battle with addiction that included drinking, drugs, and club hopping, which landed her in rehab at a young age.
Clearly, the mom of daughters Olive and Frankie has moved past her wilder beginnings — but she is still happy living life on her own terms.
Angelina Jolie
Angelina Jolie has a history of making a splash when it comes to her relationships (after all, Brangelina was an era), but her former marriage to Billy Bob Thornton, which ended in 2003, had many people giving the two some side-eye. They definitely made headlines while rocking the red carpet and exhibiting some vampire-ish tendencies by choosing to wear vials of each other's blood around their necks. Since then, this mom's accessories haven't had this level of flair.
Britney Spears
Britney Spears had a rough couple of years nearing the end of her relationship with Kevin Federline. The pop princess was spotted partying with Paris Hilton and Lindsay Lohan, and flashed her underwear to paparazzi. And that was just the tipping point, as she shaved her head a few months later amid reports of checking in and out of rehab.
But this mom of two turned it around, and it seems like she's well on her way to being better than ever after her 13-year conservatorship finally came to an end.
Goldie Hawn
Goldie Hawn is one star who dances to the beat of her own drum in both her personal and professional life. After moving to New York to start her acting career, the Snatched star — who is a mother to three kids including Kate Hudson — got a job as a go-go dancer to pay the bills. We can imagine the wild stories she has to tell.
Madonna
Material girl Madonna is known for her wild ways, as the singer has continued to top charts with her provocative lyrics and fashions (don't forget the signature lingerie — that cone bra!). Her music — and her outspoken opinions — have been the source of much debate, with some of her videos even getting banned from air. But she really pushed the envelope when she reportedly imitated masturbating on stage at one of her concerts in Canada and was almost arrested.
Janet Jackson
Janet Jackson made waves when she secretly eloped with then-boyfriend El DeBarge at the tender age of 18. The marriage was annulled shortly after, and the "Rhythm Nation" singer put the focus back on music. Today, she's a mom of one child — a son named Eissa, who was born in 2017.
Amber Rose
Amber Rose used to be a stripper, and the former model has been called out on it many times. But she's owning her past, and she's turned all the negative comments into inspiration. Rose has become an advocate and activist for women, and she's not shy to clap back at the haters. This is one mom you don't want to challenge!
Cardi B
Like Amber Rose, Cardi B also started out as a stripper before she became a mom of two with husband Offset. It wasn't an easy time for her, though — in 2022, she revealed on the Lip Service podcast that during that time, an ex stole $20,000 from her, which she said left her "traumatized."
Gwyneth Paltrow
During an appearance on The Late Late Show in January 2023, Gwyneth Paltrow told host James Corden that her 20s in Hollywood were pretty wild — before she had kids Apple and Moses with ex Chris Martin.
"It was great — talk about doing cocaine and not getting caught," she said. "You could just be at a bar having fun, dance on the table."
