The 50 Sexiest Celebrity Bad Girls of All Time

Pretty, reckless and dangerously intriguing.

Not Available Lead
Complex Original

Image via Complex Original

Not Available Lead

Earlier this week, we brought you seven covers of the baddest chick in the music business right now, Rihanna. Her topless selfies and general devil-may-care attitude got us thinking about the biggest trouble makers who live in infamy. Whether they're the rebels who found the light again, like Drew Barrymore, or the starlets who are still showing off their naughty side, like Lindsay Lohan, we've got them on our list of The 50 Sexiest Celebrity Bad Girls of All Time. Click through and enjoy the lawbreaking, the Playboy covers, and alcohol-fueled nights with the best of them.

RELATED: Rihanna Covers Seven Special Editions of Complex's February/March 2013 Issue! 

RELATED: The 50 Most Infamous Actresses of All Time 

RELATED: The 50 Hottest Femmes Fatales of All Time 

 

50. Taylor Momsen

Not Available Interstitial

Occupation: Singer, Actress


Remember the cute little girl who played Cindy Lou Who in How the Grinch Stole Christmas? This is her. She now fronts the alt-rock band The Pretty Reckless. On stage, porn star Jenna Haze nuzzled up into Momsen's crotch while she performed. And most recently, Momsen and Haze appeared in FHM topless together. What the former Gossip Girl star will do next is anyone's guess.

49. Tara Reid

Not Available Interstitial

Occupation: Actress


Reid is best known as the innocent virgin in American Pie, but her real-life antics are the antithesis of her claim-to-fame character. The actress has posed for Playboy, is the repeated victim of wardrobe malfunctions, is known for her public drunkenness, and knows her way through a rehab program. We won't mention her plastic surgery gone wrong.

48. Joan Crawford

Not Available Interstitial

Occupation: Actress


Crawford was one of Hollywood's biggest stars, but her personal life, as described by her adopted daughter, showed her as an abusive alcoholic mother. Crawford even has a whole movie, Mommie Dearest, dedicated to how batshit crazy she was. She was also involved with one of the worst Hollywood feuds in history with Bette Davis, who said, among other things, "Vodka was Joan Crawford's life support system."

47. Bijou Phillips

Not Available Interstitial

Occupation: Actress


The daughter of John Phillips, of the Mamas and the Papas, moved into her own New York City apartment when she was only 14, after quitting school. During her early teen years, she'd frequent nightclubs and was known to smoke, drink, and do drugs. After sowing her wild oats at such a young age, Bijou became more focused on her career, taking roles in Almost Famous and Hostel: Part II.

46. Tonya Harding

Not Available Interstitial

Occupation: Ice Skater


The picture of innocence should be a petite blonde ice skater. The American figure skating champion, however, is no angel. The end of her competitive career was marked by multiple issues; television commentators even said no competition would be complete without something going wrong in Harding's life, like when she had to restart her skate because the back of her dress came open.

Harding, however, is best remembered for her attack on fellow skater, Nancy Kerrigan. Her ex-husband and her body guard hired a man to break Kerrigan's leg, but he only bruised it. The blonde, though, continued to say she was innocent in the event, and now has an angel tattooed on her lower back to prove it, we guess. Oh, and her ex also released a sex tape of their wedding night. Sounds like a cool guy.

45. Bai Ling

Not Available Interstitial

Occupation: Actress


Apparently, one of Bai Ling's favorite things to do is to wear the least amount of clothing humanly acceptable on the red carpet. She's also known for her reckless behavior, too, specifically when she was arrested at LAX for shoplifting two magazines and a package of batteries. Why? It was an "emotionally crazy" day and she was dealing with breaking up with her boyfriend before Valentine's Day.

But it gets weirder. In 2009, Ling claimed she was from the moon, and her grandmother lives there.

44. Amy Whinehouse

Not Available Interstitial

Occupation: Singer


Winehouse had an incredible talent that the world will miss, but her career was imbued with her battle with substance abuse and her struggle with violent mood swings. She cancelled a number of shows in the UK in 2007, blaming exhaustion, and was later hospitalized for an overdose of heroin, ecstasy, cocaine, ketamine and alcohol.

Beyond that, Winehouse had a number of run-ins with the law, namely for punching a fan in the face, getting arrested for marijuana possession in Norway, and being taken into custody when a video of her, supposedly smoking crack cocaine, was given to the police.

43. Winona Ryder

Not Available Interstitial

Occupation: Actress


With her first starring role in Beetlejuice, as a goth who talks to ghosts, and her cult hit Heathers, in which she plans the suicide of numerous teens at her high school, it's understandable that Winona Ryder isn't an angel. In 2001, Ryder became infamous after her arrest for shoplifting. She was accused of stealing $5,500 worth of designer clothes and accessories at a Saks Fifth Avenue store. At the trial, it also surfaced that she had been using oxycodone, diazepam and Vicodin without valid prescriptions.

42. Rose McGowan

Not Available Interstitial

Occupation: Actress


The former Charmed actress shocked viewers at the 1998 VMA's when walked the red carpet with her then boyfriend, Marilyn Manson, in what could be called a glorified string, flashing off most of her body.

And her upbringing is just as eye-opening. McGowan, who's a staple in Robert Rodriguez movies, was raised in a cult, called Children of God, but her and her family fled when they moved back to the U.S., and she became emancipated at age 15.

41. Lily Allen

Not Available Interstitial

Occupation: Singer


Lily Allen is a doting mama now, but the artist known for her sarcasm-laced pop songs wasn't always someone you'd picture to be mom of the year. She dropped out of school when she was 15, was arrested for assaulting a photographer, and insulted numerous sexy famous ladies (which she later explained as a self-esteem issue).

Some other highlights of Lily's bad girl act include: telling Elton John to "fuck off" onstage and enjoying too many cocktails at the Cannes screening of How to Lose Friends and Alienate People, which resulted in a picture of her slumped over at a table with a cigarette in her hand.

40. Eve

Not Available Interstitial

Occupation: Rapper


The self proclaimed "pit bull in a skirt" was the only female signed to Ruff Ryders during her debut in 1999, so she had to be bad. Eve once spent a night in jail after a DUI and earned herself an alcohol-detecting ankle bracelet.

39. Anna Nicole Smith

Not Available Interstitial

Occupation: Model


The late Anna Nicole Smith was always a bad girl with a heart of gold. The blonde bombshell dropped out of high school and then married the oil business mogul, J. Howard Marshall, who was 62 years older than her, which inspired a lengthy trial over the estate between Smith and Marshall's son. She was addicted to prescription medications and often appeared drunk or on drugs at red carpet events, like at the American Music Awards in 2004.

38. Shannen Doherty

Not Available Interstitial

Occupation: Actress


In the '90s, Doherty was the "It" bad girl. Her diva antics and tension with her fellow co-stars earned her the boot from Beverly Hills, 90210 and her next show, Charmed, she posed for Playboy, was sentenced to 10 days in jail for drunk driving, and married Rick Soloman, who you may remember from the hit film, One Night in Paris.

37. Nicole Richie

Not Available Interstitial

Occupation: Reality TV Star


Richie's known for her successful marriage to Joel Madden and being a devoted mother of two now, but once upon a time she was the brains of The Simple Life and all over the news for driving under the influence on the wrong side of a L.A. freeway.

36. Katie Price

Not Available Interstitial

Occupation: Model, Singer


Price, one of the most infamous women in Britain, shot to fame after her topless glamor shots appeared in Page Three, and has become well known for her highly publicized relationships. She was criticized for sexually explicit behavior on her reality show, Katie and Peter, with ex-husband Peter Andre, when they talked frankly about sex and reenacted their own sex lives while fully clothed for the cameras. She is currently celebrating her fifth engagement, to a male stripper.

35. Ke$ha

Not Available Interstitial

Occupation: Singer


Allegedly, Ke$ha, before she will leave for the day, brushes her teeth with a bottle of Jack. But moving on from her pro-party lyrics and insane fashion sense, we'd like to discuss Ke$ha's new favorite thing: collecting teeth. More specifically, collecting teeth that her fans send her. She asked her fans to send her a tooth and was able to make a bra, headdress and earrings out of the 1,000+ chompers she received.

34. Tila Tequila

Not Available Interstitial

Occupation: Model/Reality TV Star


Tequila gained her famous name after she started experimenting with alcohol at 13. She started her career with Playboy and became the first Asian Cyber Girl of the Month, but she's probably best known for her bisexual dating show, A Shot at Love with Tila Tequila. 

In 2011, a sex tape with adult film actresses Kristina Rose and Charlie Laine was released, without her consent, and in 2012, she checked into rehab after trying to commit suicide by overdosing on pills.

33. Diana Ross

Not Available Interstitial

Occupation: Singer


The great Diana Ross is known around town to be a bit difficult, but she should be. She's Diana Ross. She's been slapped with an extreme DUI when her blood alcohol content was nearly over triple Arizona's .08 maximum, earning her two days in jail. Most recently, Ross threw a tantrum in a L.A. restaurant when they wouldn't seat her as she waited for her daughter to arrive. Instead, Ross sat herself. The manager then had to tell her that she wouldn't be served if she remained, and Ross refused to move.

32. Michelle Rodriguez

Not Available Interstitial

Occupation: Actress


Rodriguez always plays the tough girl in her films, and that role doesn't stop when the cameras do. She was once arrested for assaulting her roommate, was involved in a hit-and-run and a DUI, which put her in jail for 48 hours, and was repeatedly pulled over in Hawaii during the filming of Lost for speeding.

31. Sarah Silverman

Not Available Interstitial

Occupation: Comedian, Actress


Silverman's a well-respected comedian but that, of course, doesn't mean she's Bill Cosby-clean, especially since her shtick is covering issues like racism, religion, and sexism. She used a racial slur that angered the Media Action Network for Asian Americans in 2001, and she staged a one-night stand with God on The Sarah Silverman Program.

30. Amber Rose

Not Available Interstitial

Occupation: Model, Singer

On the surface, Amber Rose is best known as Kanye West's ex-girlfriend and Wiz Khalifa's fiance. However, those who've read up about her are well-versed on her stripper past, her history of leaked nude photos and her constant stream of feuds, most notably with Kim Kardashian.

Recently, however, the outspoken celeb has kept a relatively low profile as she anticipates the birth of her child with Khalifa.

29. Lady Gaga

Not Available Interstitial

Occupation: Singer


Gaga is all about being a role model, and she isn't out getting DUIs or getting arrested for possession like the other ladies on our list. What she is doing, however, is making statements with her fashion and lyrics that people like extreme conservatives often deem "demonic."

28. Mischa Barton

Not Available Interstitial

Occupation: Actress


The former O.C. actress had a few brushes with the law. She was arrested for suspicion of driving under the influence, possessing marijuana, and driving without a valid license in 2007.

In 2009, Barton was involuntarily held by a psychiatrist after seeking medical attention for a tooth infection. On the issue she said, "If they feel you are depressed or a danger to yourself they can hold you on a 5150. I am terrified of needles and they wanted to pump me full of drugs and I said, 'No, absolutely not. I don't want to be here,' and got into a fight with the nurses, and that led to my 5150."

27. Gia Carangi

Not Available Interstitial

Occupation: Model


Often considered the first supermodel, and depicted in Gia by fellow bad girl Angelina Jolie, Carangi has become better known for her troubled life than her photoshoots. In the midst of her bubbling modeling career, she began to frequent Studio 54 and Mudd Club, started using cocaine and developed a heroin addiction, and started a unstable lesbian relationship with a makeup assistant, Sandy Linter.

Additionally, Gia would fall asleep in front of the camera, had breakdowns when she couldn't find her drugs, and drew negative attention when her track marks weren't concealable even after airbrushing. Tragically, Gia died of AIDS-related complications at the age of 26.

26. Lisa "Left Eye" Lopes

Not Available Interstitial

Occupation: Singer


Left Eye's rapping made TLC unforgettable, but her personality made her irreplaceable, and she constantly challenged her band mates to solo album sale competitions. Infamously, when her former boyfriend, NFL player Andre Rison, pissed her off, she set his shoes on fire, which resulted in her burning down the house.

25. Christina Aguilera

Not Available Interstitial

Occupation: Singer, Actress


The former Mousekeeter and bubble-gum pop star left that persona in the dust when she reinvented herself in the video for "Dirrty," and appeared nude on the cover of Rolling Stone. In the transition from good girl to bad girl, she dyed her hair black, called herself "Xtina," which she got tattooed on the back of her neck, and got some piercings.

24. Foxy Brown

Not Available Interstitial

Occupation: Rapper


Brown was always barely dressed onstage, which complemented her explicit lyrics. However, Brown's bad girl antics in real life have always given her just as much attention as her rhymes. Between the years 1997 and 2007, Brown spat on two hotel workers when she found out an iron wasn't available, crashed her Range Rover and was arrested for not having a license, assaulted a beauty supply store employee, hit a neighbor with her BlackBerry, and almost ran over a stroller with a baby inside. She was also sentenced to jail for a fight that happened in 2004 when she attacked two manicurists because she didn't want to pay $20.

23. Paris Hilton

Not Available Interstitial

Occupation: Reality TV Star


Hilton's been a wayward girl long before One Night in Paris. When she was 16, she spent a year at a school for emotionally troubled teens. At 18, she was kicked out of her high school. And at 19, she was considered "New York's leading It Girl" and was absorbed into the L.A. party scene. 2006 started Hilton's streak of car troubles (namely a DUI and a suspended license) and, in 2007, she also spent some time in jail. Most recently, in 2010, Hilton was suspected of smoking marijuana at a FIFA game, and was arrested on suspicion of cocaine possession in Las Vegas.

22. Courtney Love

Not Available Interstitial

Occupation: Singer

Love had a promising career in rock 'n' roll with her band, Hole, but drugs and drama have turned her into a TMZ staple. Recently, Love is best known for her rants on Twitter, including posting some risqué photos of herself and guilt-tripping her estranged daughter.

21. Lana Turner

Not Available Interstitial

Occupation: Actress


Turner started off as the innocent girl in the soda shop, but she became a real life femme fatale. Her daughter, Cheryl Crane, stabbed Turner's abusive lover to death. She also ended up having six husbands, including the band leader, Artie Shaw, whom she married the night she met him, and dating mobster Johnny Stompanato.

20. Whitney Houston

Not Available Interstitial

Occupation: Singer


We will always love Whitney Houston, but the singer had an undeniably infamous history. We watched as Houston's star rose, and we witnessed her constant battle with addiction. She was in a turbulent relationship with Bobby Brown and constantly refused to admit she was on drugs, telling Diane Sawyer, "Crack is cheap. I make too much money to smoke it... We don't do crack... Crack is whack."

19. Sharon Stone

Not Available Interstitial

Occupation: Actress


You don't need this blurb to tell you how, uh, eccentric, Stone is, but we'll indulge you anyway. She flashed her privies as the femme fatale in Basic Instinct, she wears numerous see-through dresses, she babbles at award shows, she lied for years about being in MENSA, and she hinted at bisexuality by saying, "Middle age is an open-minded period." Yeah, we think we got most of it.

18. Lil' Kim

Not Available Interstitial

Occupation: Rapper


Kim's lyrics have been dubbed "gagsta porno rap," she's known to feud with fellow female artists (including Foxy Brown, Eve, Shyne, and Nicki Minaj), and she doesn't shy away from showing off a little skin when it comes to the red carpet. Her most infamous moment, however, was when she was sentenced to one year and a day in prison in 2005 for lying to a federal grand jury about a shootout in front of a Manhattan radio station in 2001.

17. Mae West

Not Available Interstitial

Occupation: Actress


The old Hollywood star was a sex symbol for seven decades. She could turn a phrase better than any, and was well known for her lewd double entendres. Her own play, Sex, earned her and her cast 10 days in jail for "corrupting the morals of youth."

16. Drew Barrymore

Not Available Interstitial

Occupation: Actress


Drew Barrymore grew up like your cousins who live in the dodgy parts of the Appalachians. She started smoking cigs at nine, drank by 11, smoked marijuanna by 12, and snorted cocaine at 13. The only difference is she got to hang out with the stars at Studio 54 when she was a preteen. At 13, she was already in rehab, and at 14, a suicide attempt landed her back in it again. She's posed nude twice, at ages 17 and 19, and once flashed David Letterman.

Nowadays, her younger self wouldn't even recognize her. Barrymore is focusing on being a mom. 

15. Sienna Miller

Not Available Interstitial

Occupation: Actress, Model


Sienna Miller, before settling down with her kid and baby daddy Tom Sturridge, was branded as a homewrecker. When she first hooked up with Jude Law, he was still married to Sadie Frost. However, what really got the public's attention was her affair with married father of four, actor Balthazar Getty. 

14. Megan Fox

Not Available Interstitial

Occupation: Actress


From the get-go, Megan Fox was touted as the next Angelina Jolie, i.e. Hollywood's next great bad girl, despite the fact that she truly never got caught in the web that Lindsay Lohan still hasn't entangled herself from. A sign of her Jolie-like rebelliousness, Fox once told GQ that when she was 18, she dated a female stripper. However, she has since admitted that she embellished her bisexuality stories for male writers, and that she was only obsessed with a female stripper, not dating her.

Most infamously, she called Michael Bay Hitler, and while Bay is responsible for making her a sex object in the movie, she was held accountable for the name-calling and fired from Transformers.

13. Vanessa Hudgens

Not Available Interstitial

Occupation: Actress


Hudgens's leaked nude photo scandal is well known. The first surfaced when she was only 17, and more came out when she was 19, including one of Hudgens making out with Nickelodeon star Alexa Nikolas. Now, she's officially taking the leap from Disney-girl-caught-in-a-mistake to owning her bad girl image for her upcoming film Spring Breakers.

12. Miley Cyrus

Not Available Interstitial

Occupation: Actress, Singer


The former Hannah Montana was a Disney good girl, but in 2007, when Cyrus was 15, all that changed with one MySpace picture of her and a friend sharing a piece of licorice and almost kissing. In 2008, pictures of her in her underwear were leaked, and she posed topless for Vanity Fair. By 2009, at 16, Miley began accepting her bad girl persona and performed a pole dance at the Teen Choice Awards that infuriated moms everywhere. At her 18th birthday party, pictures of Cyrus with a bong were released.

Nowadays, Cyrus is killing it with how she's grown from a typical troubled teen to a confident HBIC. The soon-to-be Mrs. Liam Hemsworth is working on new music and her producer, Pharrell, says her new sound is "powerful and unexpected."

11. Kim Kardashian

Not Available Interstitial

Occupation: Reality TV Star


Most people who become famous because of a sex tape are often referred to as porn stars. Not Kim Kardashian. When her video with Ray J was leaked, she became a major fixture in pop culture, earning her a reality TV show and a feature in Playboy. Also, she divorced her ex-husband Kris Humphries after 72 days of marriage, and started dating Kanye West while still married to the NBA player. 

10. Elizabeth Taylor

Not Available Interstitial

Occupation: Actress


If you sat through the Lifetime movie Liz and Dick (you know, the one with Lindsay Lohan in the leading role), then you already know some fun facts about Taylor, including the fact that she was married eight times, to seven men. She married and divorced Richard Burton twice, the turbulent relationship driving her to attempt suicide.

After her third husband died, she began self-medicating for a short time with pain killers, and used alcohol throughout her life. In 1981, she had over 300 prescriptions for 30 different pills, before entering rehab in 1983.

9. Madonna

Not Available Interstitial

Occupation: Singer


Madonna has kept herself relevant throughout the years by constantly reinventing her style and music and maintaining her rebellious persona. Her fashion and suggestive lyrics often sparked controversy, such as her hit "Like a Virgin," which many found offensive when the iconic pop star toed the line between Mother Mary and, well, the antithesis of Mother Mary.

Now, any controversial moment the singer is involved in is no longer a surprise. When the live kiss between Madonna and Britney Spears aired during MTV VMAs, the world let out a collective, "Yeah, that makes sense."

8. Britney Spears

Not Available Interstitial

Occupation: Singer


We've got this picture up at the office to remind us it only gets better. Spears started off as an innocent Mouseketeer of The Mickey Mouse Club and was already flirting with naughtiness in the video for her first single, "Baby One More Time." She married the persona of childhood innocence and adult sex appeal by maintaining that she'd remain a virgin until marriage, while posing in a bra and short shorts on Rolling Stone.

However, things quickly spiraled out of control. Spears had a drunken Vegas wedding and an annulment 55 hours later, married (and eventually divorced) a back-up dancer, K-Fed, after three months, and infamously spent one night in drug rehabilitation, before shaving her hair off the following evening.

Recently, Spears has quit being a judge on the X Factor because they wanted to fire her for being too normal. We're proud of you, Britney.

7. Paz de la Huerta

Not Available Interstitial

Occupation: Actress, Model


Between being Jack Nicholson's date for The Departed premiere to make her boyfriend jealous and rubbing honey on her breasts in a sauna during an interview, de la Huerta's become a gold star member of the Bad Girls Club. In fact, we look forward to her next escapade. Here are our guesses as to what she'll do next: fight a bear or start a cult. 

6. Naomi Campbell

Not Available Interstitial

Occupation: Model


When Mike Tyson describes someone as "afraid of nothing," then you shouldn't be surprised by her number of assault cases. Between 1998 and 2008, Campbell, who's notorious for her hot temper, was accused 10 times of committing violent acts against her employees, associates, and, once, a police officer. In 1999, Campbell entered rehab for her five-year addiction to cocaine. 

While Campbell's reputation will always precede her, she's becoming well-respected for her charity work and for speaking out about discrimination.

5. Tallulah Bankhead

Not Available Interstitial

Occupation: Actress


Bankhead was the OG of actresses who are more famous for the crazy personal antics than their actual career. She was a known bisexual who famously said, "My father warned me about men and booze, but he didn't mention a word about women and cocaine." Additionally, she had numerous Hollywood feuds, was known to go commando, lost a Tallulah Bankhead impersonation competition, and told Joan Crawford, "Darling, you're divine. I've had an affair with your husband. You'll be next." And rumors were, she tapped Joan, too.

4. Lindsay Lohan

Not Available Interstitial

Occupation: Actress, Singer


Lohan is the poster child of good-girls-gone-bad. She started as a promising young star in the adorable Disney flick, The Parent Trap, and moved on to the iconic comedy Mean Girls, where she played the fish-out-of-water girl-next-door.

Nowadays, however, she's better known for her DUIs, stints in rehab and jail, tumultuous interpersonal relationships, and now Stephen Rodrick's New York Times piece, in which all her actions on her latest softcore-porno-esque film, The Canyons, are well documented.

3. Kate Moss

Not Available Interstitial

Occupation: Model


Moss is well known for promoting the heroin chic look in modeling, and advancing the popularity of the size-zero body type. She's also well known for snorting five lines of coke in 40 minutes at a Babyshambles recording session (which was captured on camera and published in the Daily Mirror).

After the incident, H&M and Burberry dropped her as spokesperson, and Chanel chose not to renew her contract. Yet, after a successful stint in rehab, Moss regained her modeling fame. It's as if the past never even happened.

2. Rihanna

Not Available Interstitial

Occupation: Singer


Our February/March cover girl sings it herself: "I may be bad but I'm perfectly good at it." Rihanna is out of craps to give; she explicitly sings about sex, regularly appears nude, takes Instagram photos of her love the sticky-icky, and is back with bad boy Chris Brown. Yeah, she's quite easily one of our favorite bad girls of the moment.

1. Angelina Jolie

Not Available Interstitial

Occupation: Actress


Who doesn't fondly remember the crazy days of Jolie? It's like looking back at college pictures of yourself and remembering the glory days when you just DGAF-ed about everything. Her most memorable moments include: wearing a vial of Billy Bob Thornton's blood around her neck, kissing her brother on the red carpet, and admitting to cutting her ex-boyfriend in the bedroom for pleasure. 

Despite her settled-down lifestyle as a doting mom of six, the legend of bad girl Angelina Jolie will always be a prominent part of Hollywood history.

Latest in Pop Culture