There’s nothing the tabloids love more than a celebrity “good girl gone bad” story, and between actresses, musicians, and famous-for-being-famous types, there’s been more than a few of them to gawk at. It’s almost like seeing a car crash—you just can’t look away. But at the same time, there are often tragic backstories that precede the whole “going bad” thing. Whether it’s a child actor who took a wrong turn or a squeaky clean pop star who went off the deep end, there’s usually more to their stories than just a DUI or some weird tweets. Put on your best mugshot face for these scandalous facts about celebrity “good girls gone bad.”
1. Ugly Court Battles 101
If you’re certain age, you might remember that Nickelodeon’s Zoey 101 became awkward when its star, Jamie Lynn Spears, became pregnant in 2007. What’s less talked about is how her boyfriend at the time, Casey Aldridge, faced legal repercussions because he was about 18 while Spears was 16. He narrowly avoided getting charged but did plead guilty to a misdemeanor.
Aldridge did not reside in California where the show was shooting at the time, and he was just less than two years older than Spears, so he narrowly missed the legal cut off.
2. Reese’s Run-in
Surprised to see Reese Witherspoon on this list? The starlet had a squeaky clean image until a 2013 viral tape showed her screaming at a police officer while being arrested for disorderly conduct. She later revealed the bizarre details behind the incident. Witherspoon shamefully confessed to bold-faced lying to the officer during the incident.
As she said, “I saw [the cop] arresting my husband and I literally panicked. I said all kinds of crazy things. I told him I was pregnant. I’m not pregnant! I said crazy things.”
3. Uncovering Scandal
Jessica Biel first rose to fame in the 1990s as Mary, the adorable daughter on 7th Heaven. At the age of 17, however, Biel posed for a racy photoshoot which graced the cover of Gear magazine. 7th Heaven had built its entire image on wholesomeness, and they did not appreciate Biel’s look. Biel was promptly written off in the show’s fifth season.
Michelle Rodriguez’s character Ana-Lucia on the hit show Lost was a divisive one for fans—she didn’t seem to have a purpose, took screen time away from the main cast, and messed with the fan-favorite pairing of Jack and Kate. Off-screen, Rodriguez was partying too hard and was ultimately caught drinking and driving for the second time in a year.
“Coincidentally,” her character was abruptly killed off in the show. There seems to be a pattern here.
5. Goblet of Fire
While filming Chinatown, tensions ran high on set, but few could’ve predicted just how bad things would get. After director Roman Polanski forbid star Faye Dunaway from taking any bathroom breaks, her reaction was bone-chilling. She reportedly threw a cup of her own urine in Polanski’s face. Can we blame her?
6. My Bloody Valentine
It seems like eons ago that Angelina Jolie and Billy Bob Thornton were still together. And wearing necklaces of each other’s blood. According to Thornton, it was Jolie’s idea that “it would be interesting and romantic if we took a little razor blade and sliced our fingers, smeared a little blood on these lockets and you wear it around your neck just like you wear your son or daughter’s baby hair in one.”
In terms of romantic gestures, we’d have gone with the hair thing; more Victorian, much less painful, and way more hygienic.
7. Precious Prize Winner
Tatum O’Neal is the youngest Oscar winner in any category. She won the 1973 Academy Award for Best Supporting Actress, for her role as Addie in Paper Moon, when she was just 10 years old. She starred in the film opposite her father, who she would later claim physically and emotionally abused her when she was a child, also claiming that her father’s drug dealer assaulted her while visiting him when she was just 12 years old.
Later in life, following her divorce, O’Neal struggled with substance abuse.
8. First Love
Tatum O’Neal was Michael Jackson’s first girlfriend and, allegedly, his first real love. Jackson once said in an interview that during their time together, she had tried to seduce him, but the idea of sex terrified him so he backed off. For years, it was widely believed that Jackson had lost his virginity to O’Neal, but in 2004 she shocked the world when she categorically denied this in her book.
According to her, the two of them kissed, but never did anything more—the tabloids had made their relationship seem far more scandalous than it had been in real life. However, she also denied Michael’s claim that she tried to seduce him.
9. A Nightmare at McKinley High
Lea Michele earned herself the title of “diva” after what went down on the set of Glee. Apparently, Michele hated her co-star Naya Rivera, trying to get her fired from the show, and was rude and impatient, even snapping her fingers at crew member when a delay was interfering with her evening’s plans.
Guest star Kate Hudson, who played Michele’s dance teacher, was said to have kept her distance. Good call, Kate.
10. I’m Not Cleaning Out That Closet
When rapper Azealia Banks burst onto the scene with a hit song, many thought she’d be the next Nicki Minaj. But while her fans were patiently waiting for her to release new music, Banks was busy casting spells and sacrificing animals. In 2016, a series of now-deleted Instagram videos showed Banks talking about brujeria—a type of magic—and complaining about having to clean the blood-stained closet where she ritually killed chickens.
11. Desert Breakdown
Anne Heche was a film and TV star in the ’90s, but was mostly known for being one half of Hollywood’s most famous lesbian couple, when she dated Ellen Degeneres. Shortly after the two broke up, Heche took ecstasy, which triggered an unfortunate mental breakdown that received a huge amount of attention—probably because of its utterly bizarre nature.
12. Now That’s a Hangover and a Half
Heche was found in a stranger’s house in the desert, claiming to be God and that her spaceship was waiting for everyone—she even made up her own language to communicate with the aliens. Well to her credit, the aliens probably wouldn’t have spoken English, so maybe she was on the right track?
13. I Did What?!?
In 2013, a bizarre sequence of events led to Zooey Deschanel being named a suspect in the Boston Marathon bombing. She woke up to find her name mentioned across social media and the story began to come together: on a Fox newscast, the anchor has read the name “Dzhokhar Tsarnaev,” but the closed captioning had misunderstood it as “Zooey Deschanel,” leading to a caption that identified her as the main suspect in the bombing.
Okay, so she didn’t actually go bad, but I guess everyone thought she did for a hot minute. Deschanel later received an apology from the network affiliate and the company that handled their captioning.
14. Charlie Needs to Mediate this One
Lucy Liu was at the top of her career when she appeared in Charlie’s Angels. She’d appeared on Ally McBeal for multiple seasons without any stories of on-set meltdowns, but then, Liu allegedly attacked Bill Murray, screaming and throwing punches at his face. But there are two sides to every story…
15. Fired Up
Was she justified? Moments before, Bill Murray had stopped a scene in progress, apparently in order to compare Lucy Liu to her co-stars Drew Barrymore and Cameron Diaz. He praised the two other actresses, then pointed to Liu and asked, “What in the hell are you doing here? You can’t act!” Nice Bill, real nice. He was replaced by Bernie Mac for the sequel.
16. Just Plain Depressing Affair
Anissa Jones began playing Buffy in the 1960s sitcom Family Affair at the age of only 4. Her real family life was less than idyllic: Jones’ mother went to disturbing lengths to maintain their lucrative marketing deal to sell Buffy-style clothing. She forced Anissa to wear her hair in childish pigtails and baby doll dresses until she was 13.
After Jones retreated to friends’ homes in the wake of her father’s death, her mom reasserted control by reporting Jones as a runaway and having her jailed as delinquent. Anissa Jones died of an overdose at the age of 18.
Bijou Phillips, daughter of Mamas & Papas singer John Phillips, gained fame acting in several horror and drama films throughout the 2000s. But since then, things haven’t gone so well. Bijou was accused by former co-stars of abusive and bullying behavior. Daniel Franzese, best known for Mean Girls, said that Phillips made fun of his weight and sexuality.
Heather Matarazzo alleged that he was physically assaulted by Phillips. Phillips has since apologized for her behavior.
18. Setting the Story Straight
Though Mandy Moore is known for her good girl image, in 2006 her ex-boyfriend Wilmer Valderrama made some pretty scandalous comments to Howard Stern about Moore’s intimate life. The actor claimed that he had taken Moore’s virginity and also commented cruelly that, “The sex with Mandy was good, but it wasn’t like warm apple pie.”
19. Clap Back
At the time, Moore called him out for lying about taking her virginity, and even more recently she herself went onto Stern’s show and revealed more wild details about Valderrama’s icky rumor. “‘Where did this come from?’” she remembered asking him at the time when she called him up. “And I remember in the moment he tried to explain it away, that sort of he did get caught up, and like he maybe insinuated more than outright said it. And I was like, ‘No, you outright said it.’”
She then continued, “I met him at a photoshoot for like, some teen magazine, literally, when I was 15? 15! I was [pretty innocent!] … Again, never French kissed a boy. He was like my first real true boyfriend. [But] he did not [take my virginity].”
20. You’re Toxic
Ryan Gosling confessed he feels responsible for corrupting Britney Spears on The Mickey Mouse Club. He says, “They would come and ask me questions about sex, and I just told them what I heard – like positions and stuff. All the other mothers went to Disney and told them I was corrupting their kids. I feel somewhat responsible for how sexual she is right now. When I see her with a snake around her neck, I think, ‘Did I do that?’
21. Dangerous Liaisons
One of Michelle Pfeiffer’s earliest roles was playing the innocent and ill-treated Madame Marie de Tourvel in Dangerous Liaisons. She played opposite John Malkovich, who had the infamous role of the unprincipled Valmont. As might be expected on the set of a film about scandal, it was soon reported that the married Malkovich had begun an affair with Pfeiffer.
The affair did not last, but neither did Malkovich’s marriage.
22. Off the Deep-End
Miley Cyrus has, to put it mildly, had a roller-coaster decade with the American public. The daughter of country-music sensation Billy Ray Cyrus, Miley at first cut a pure and innocent figure through her Disney-channel show. That changed around the mid-2010s when things got a little more…adult. At the height of the antics came the announcement that she would be performing a fully nude concert with The Flaming Lips as her backing band.
Well, Wayne Coyne was certainly never one for subtlety!
23. Up in Smoke
In what can only be described as a “stoner phase,” Billy Ray Cyrus’s once innocent TV star daughter, Miley Cyrus, got really into smoking weed. In fact, it became a part of her tribute to her dog Floyd after he died. To honor her beloved pet, Miley built a massive, light-up bong.
24. Dirty Halle
Halle Berry visited a real crack den to prepare for her role in Jungle Fever. She also didn’t bathe for two weeks.
25. Into the Family
Everyone knows that Nicole Richie is the famous writer and socialite daughter of musician Lionel Richie, but did you know that she was actually adopted? Nicole’s biological parents, also musicians, could not afford to raise the young girl and when Lionel Richie met them at a Prince concert when Nicole was just 2, he agreed to take her into his home.
26. Trouble with the Law
Growing up with a famous dad in the middle of a bitter and public divorce, Nicole Richie herself claims that she was allowed too much freedom while growing up. The result was a series of public run-ins with the law during the 2000s. While filming her reality show with friend Paris Hilton, Ritchie was arrested for a DUI and eventually spent four days in jail.
27. Enhancing the Image
After a series of run-ins with the law and DUI arrests, Nicole Richie decided she wanted to change the way the public perceived her, and she became invested in a number of philanthropic endeavors with her partner Joel Madden. “The Richie Madden Children’s Foundation” has done a number fundraisers for UNICEF since 2007, including a public-service announcement to raise funds for Myanmar after the country was rocked by a devastating cyclone.
28. Runaway Bride
In the late ’80s and early ’90s, Julia Roberts had a reputation as something of a runaway bride (perhaps leading to her casting in a film of the same name in the late ’90s). She became engaged to Dylan McDermott after they appeared in Steel Magnolias together, but broke it off when she met Kiefer Sutherland while making Flatliners. There was just one problem.
Sutherland was already married at the time with a child, but he soon announced his engagement to Roberts.
29. No Hard Feelings
A huge wedding was planned, but three days before, Roberts made a shocking decision. She called it off and ran away to Ireland with Sutherland’s good friend Jason Patric. Recently, Sutherland revealed he holds no grudges about the whole debacle, saying that Roberts was smart to get out while she did.
30. The Child Star Stereotype
The story of Amanda Bynes is a familiar one in the world of child stars. With a promising start from a very young age, Bynes was absorbed into show business back when the rest of us were still in school. She was on TV for what seemed like an entire decade, with programs like The Amanda Show and What I Like About You, but shortly after her transition to film, Bynes began exhibiting troubling behavior.
31. Just a Taste
Bynes began smoking pot when she was a teenager, only to move on to ecstasy and prescription pills later on in her life. By her own admission, she never turned to more serious illegal substances, as many of her peers have done, but it’s hard to dispute that mind-altering substances didn’t play a role in her image in the late 2010s.
32. Bad Times, Good Times
Bynes had a very negative reaction from her own performance in She’s the Man. In 2018, Bynes admitted that she developed body issues from looking at herself when she had been dressed up as a boy—which constitutes a majority of the plot, we should add. Bynes reportedly went through a period of depression which lasted nearly half a year.
33. Mea Culpa
As some of you might remember, Amanda Bynes came under fire while filming scenes for the comedy Hall Pass. Rumors persisted in the tabloids that her disruptive behavior had led to her being fired from the production. However, in 2018, Bynes admitted that she had actually left of her own accord, abandoning the film.
Explaining that she had been seriously struggling with an Adderall addiction at the time, she expressed her regret for being so “unprofessional” back then.
34. Falling Apart
In April of 2012, Bynes was arrested for driving under the influence after she hit a stopped police car then refused to take a sobriety test. This was the start of a series of bizarre public lash-outs and run-ins with the law that would plague her over the next year. Her mental state appeared to deteriorate and she began sending out frequent and bizarre tweets, such as appealing to Barack Obama to fire the cop that arrested her or claiming she invented the phrases ILY and LOLOL. But that wasn’t the end of it.
35. Fighting Words
Amanda Bynes also got into very public spats with celebrities such as Jenny McCarthy, whom she called an ugly old lady who “look[s] 80 compared to me.” In this time, she was charged with two hit and runs. Eventually, after one final arrest, Bynes was hospitalized for 72-hours for a mental-health evaluation and her parents decided it was time to step in.
36. Stepping In
Due to her various legal troubles and clearly frayed mental state, Bynes’ parents filed for conservatorship of their daughter in 2013, meaning they gained control of her affairs as she was deemed mentally incapable of managing them herself. Bynes’ mother received this conservatorship over Bynes’ affairs, which continued to be renewed in 2014.
Since then, it’s been renewed in 2018, with plans for it to continue until 2020.
37. Low Blow
During Bynes’ very public mental breakdown, when her legal troubles were beginning to pile up, fellow-child star Lindsay Lohan took the opportunity to cruelly kick her one-time rival while she was down. Lohan took issue with the fact that Bynes had not been incarcerated after her many run-ins with the law, tweeting: “Why did I get put in jail and a Nickelodeon star has had NO punishment(s) so far?”
So much for supporting your peers.
38. In the Flower of Her Youth
On December 20, 2009, actress Brittany Murphy died at the tragically young age of 32. While the cause of death was originally listed as natural causes, a subsequent report blamed her death on “a combination of pneumonia, anemia, and prescription and over-the-counter drugs.” Five months after Murphy’s death, the tragedy—and mystery—suddenly deepened. Her husband, Simon Monjack, died in the same bedroom that Murphy had been in.
39. What Really Happened?
In a disturbing coincidence, the cause of his death was also listed as pneumonia and anemia. One reason for the abrupt deaths of Murphy and her husband has been brought forward by Murphy’s mother, Sharon. Sharon maintains that her daughter and son-in-law died due to a presence of toxic mold in their house. But the story doesn’t end there.
By contrast, Murphy’s father, Angelo Bertolotti, had toxicology tests done on Murphy’s hair. The results convinced him that she and her husband were poisoned. Bertolotti has yet to make an accusation on who that poisoner might have been, and it’s worth pointing out that Murphy’s mother, Sharon, and Bertolotti hotly dispute each other’s claims.
41. Little Girl Lost
Drew Barrymore also got her start as a child actress—and the child actress who goes on to become a substance abuser is pretty much a tragic cliché at this point. However, it might make for some good reading. Little Girl Lost, Barrymore’s memoir, tells the story of her early years, including having her first smoke when she was nine and frequenting clubs just a few years later.
Barrymore completed the book when she was 14, and also released Wildflower in 2015, a followup that reveals more about her life.
How do rom coms approach the first meeting? Hands accidentally touching while reaching for something? The introduction at work? Barrymore is more original: she met one of her exes, musician Eric Erlandson, while puking outside of a club, as he stood nearby to stand guard as she did so.
43 No One Puts Batman in a Corner
Back when she was a teenager, Barrymore went on a date with Christian Bale. As Bale revealed, Barrymore never called him back. To be fair, this was the stage in Barrymore’s life where she was dealing with alcoholism and drug addiction. As Barrymore says, she “had a lot of fish to fry,” and boys weren’t at the top of her priorities.
44. Close Call
Back in 2001, Barrymore was happily dating Tom Green and they were enjoying their home in a canyon north of Beverly Hills. Things took a slight turn for the worse, however, when the home caught fire while they were sleeping. Their dog Flossie likely saved their lives by barking at their door. The fire led to about $700,000 in damage, and the house was ruined.
45. The Flash
In 1995, Barrymore appeared on The Late Show with David Letterman. While being interviewed, she brought up a scene in a film where her character does a striptease. She offered a demonstration, which led to her flashing Letterman (with her back to the camera). Barrymore has returned to the show since and says that she and Letterman developed great chemistry.
Barrymore posed nude for Playboy when she was only 19 years old. In response, godfather Steven Spielberg sent her a quilt as a gift with the note “cover yourself up.”
47. Thanks, Mom?
Barrymore’s early problems with alcoholism and substance abuse led to a suicide attempt when she was only 13, but the actress was found and taken to the hospital. Afterward, her mother went to extreme measures: she sent Drew to a mental institution, where she stayed for a year and a half. Drew says there was no warning of the institutionalization, but she realizes that she likely would have run away if her mother warned her it was coming.
Once Drew was released at age 14, she emancipated herself from her mom, legally becoming an adult. Despite this, Barrymore thinks fondly of her mom, even though the two don’t speak that often.
48. Who needs a GED?
Due to her stay in a mental institution at the age of 13, you might have been able to guess that Barrymore didn’t finish high school.
Following her suicide attempt and subsequent stay at a mental hospital, Barrymore lived with rock star David Crosby. Crosby and his wife, Jan, had their own experiences with alcohol and drug excess and tried to help ease Barrymore onto the wagon. Crosby also believed Barrymore would break the chain of alcoholism in the family, which saw its most recent victim in Barrymore’s father.
Barrymore hasn’t talked much about this experience that much, but did say she would be more “[messed] up” if it wasn’t for people like “David and Jan and Steven (Spielberg)”.
50. Best Thing That Never Happened
Despite childhood success, Barrymore’s substance abuse issues and emancipation from her mother led to a period where she struggled financially. She ended up working at a coffee shop where the owner told her she was a “bad employee.” Shortly after, Barrymore landed a role in Poison Ivy. The film didn’t se the world ablaze, but it helped nab other roles for the adult Barrymore, and we now know where that led.
51. Best Buddies
Britney Spears’ parents began preparing her for a career in show biz when she was just a young girl, and when she was old enough to go on TV, the family moved to Orlando, Florida so she could be on the Mickey Mouse Club. This is where she became friends with Justin Timberlake. They both performed covers of songs on a regular basis. Ryan Gosling and Christina Aguilera were also in the cast at the same time.
52. Childhood Sweethearts
Britney Spears and Justin Timberlake dated from 1999 to 2002. When they broke up in 2002, rumors swirled that Spears had cheated on Timberlake; he released “Cry Me A River,” a ballad about an unfaithful girlfriend, the same year. For Spears, the nightmare wasn’t over. Her parents also got divorced that year, and worse times were lurking around the bend for the pop star.
53. What Happens in Vegas…
In 2004, Spears spontaneously married her childhood friend Jason Alexander in Las Vegas. Two days later, she and Alexander annulled the marriage.
Spears’s next marriage was to her backup dancer, Kevin Federline. When Spears and Federline first got together, his fiancée Shar Jackson was pregnant with Federline’s second child.
55. Sinking Ship
Spears and Federline were married in 2004. Federline was a high school dropout while Spears was very wealthy; Spears almost got married without a prenuptial agreement before her family and management team stepped in. Spears and Federline had two children together, Sean and Jayden. They eventually got divorced in 2007.
56. I Said No, No, No
In February of 2007, Spears checked herself into rehab in Antigua for less than one day. She was emotionally struggling with her divorce from Federline, and had just gone to court over a custody battle with her ex.
57. Mrs. Clean
Just a few days after checking herself out of rehab, Spears infamously shaved her whole head. Spears got two tattoos immediately after shaving her head. When the tattoo artist asked her why she decided to shave her head, she replied, “I don’t want anyone to touch me. I’m tired of people touching me.”
58. End of the Line
In 2008, Spears was forced to enter a psychiatric hospital under California’s rule “5150,” which comes into effect if the subject is considered to be “a danger to herself, or others.”
59. Picking up the Pieces
After entering treatment, Spears temporarily lost custody of her children Sean and Jayden, for their safety. The effect on Spears was dark. After losing custody, she fell into a deep depression. Court documents reported that Spears had been using drugs and sleeping in her car.
60. Thanks, Dad
In 2008, Spears was deemed to be incapable of making her own decisions, and she needed a court-appointed legal custodian. Her father took over Spears’s finances and management decisions; papa Spears makes $130,000 a year as his daughter’s caretaker.
61. The Teenaged Heiress With a Target on Her Back
No list about the most outrageous tales of “good girls gone bad” would be complete without the case of Patty Hearst. Hearst was a beautiful heiress who was taken from her apartment one night in 1974. Immediately, a terrifying urban guerilla group known as the Symbionese Liberation Army took responsibility for the crime.
62. Rebellious Phase Gone Too Far
Hearst wasn’t seen for two months, although her captors were in contact with her family—and then, a shocking surveillance video revealed her taking part in a bank robbery alongside the very group that had abducted her. When she was later recovered and went on trial for her crimes, she claimed that she’d been brainwashed by the group—but many were skeptical.
Did the heiress have a secret dark side?
63. Did She or Didn’t She
Hearst was convicted and sent to prison for her part in the bank robbery, despite the pleas of her family and lawyers. When two of the people alleged to be part of Hearst’s kidnapping went to trial, a rat was found in her bunk—but her long and surreal nightmare wasn’t over yet.
64. Wrong Place, Wrong Time
One of Hearst’s greatest advocates at the time was a congressman named Leo Ryan. He was in the middle of collecting signatures for a petition advocating for Hearst’s release when he ended up in the middle of another horrific crime. Ryan was killed while visiting Jonestown, Guyana, as part of the terrifying Peoples Temples massacre.
Eventually, Hearst’s sentence was commuted, and since then, she’s gone on to live a relatively normal life.
65. The Other Side
Jessica Simpson has seen it all, and though the pop star may seem as sweet as apple pie, her life has been way less sugar, much more spice. From scandalous rumors to infamous exes—yes, we’re looking at you, John Mayer—Simpson has low-key been a good girl gone bad this whole time.
66. Good Girl Gone Bad
In 2005, Simpson’s good little girl image broke forever. Her steamy music video for “These Boots Are Made for Walkin’” came out alongside the 2005 film The Dukes of Hazzard—and promptly got banned in several countries. As I’m betting you remember if you’ve seen it, the video heavily featured Simpson writhing around on a car as her character Daisy Duke.
67. Newlyweds No More
2005 might have been a big career year for Simpson, but it also came with immense heartbreak. In December, she and husband Nick Lachey officially divorced. Fans were shocked, but according to Lachey, Newlyweds had driven a rift between them. As he said, “Jessica and I began playing these parts even when we were by ourselves.” But there were even more scandalous reasons behind the split.
68. The Meddler
Lachey was reportedly “blindsided” by the divorce, and an unhappy Simpson dropped the news on him in the car after they were out for dinner. To make matters worse, Lachey partly blamed Jessica’s father Joe for the split. As Lachey later said, “Was he an influence in our marriage? Absolutely.” And the bitterness didn’t end there…
69. For Love and Money
Jessica Simpson later confessed her biggest regret about her marriage to Lachey: the massive payout she had to give him. According to rumors, Joe Simpson discouraged Jessica from signing a prenup with Lachey when they married since the boy band alum was worth a lot more than her at the time. This came back to bite her in a big way.
By the time they split in 2005, Simpson was a much bigger star than Lachey, and she reportedly had to pay him a whopping $12 million to finalize their divorce. Ouch. She later called him her “biggest money mistake.”
70. Coming Back for Seconds
Few people know just how messy Simpson’s divorce with Nick Lachey got. After the papers were finalized, Simpson invited Lachey over to her house “to clear the air”—and ended up sleeping with him instead. Oh, I think we’ve all been there.
71. From Boy Band to Boy-Man
Jessica Simpson didn’t sit around moping after her divorce from Nick Lachey, oh no. Nine months after the split, she started dating crooner John Mayer—and their relationship is infamous for very good reason. For seemingly ages, the pair were on- and off-again, and Simpson’s memoir reveals the absolutely heartbreaking ordeals Mayer forced her through.
According to her, it was always Mayer breaking up with her and then taking her back, and they broke up something like nine times throughout their steamy relationship. As she wrote, “I always saw it as him mercilessly taking me in from the cold.” Sadly, that was just the beginning of the nightmare.
72. The Right Words
Simpson confessed that while she was dating Mayer, she was so insecure about herself that she would spend hours upon hours agonizing over the texts she’d send him, making sure every word was perfect and all the grammar in place. In the end, it was never enough. Thing is, we’re not even done with the havoc Mayer wreaked on Simpson’s life.
73. Portrait of a Lady
According to Simpson, Mayer was “obsessed” with her, but this obsession had a chilling dark side. Mayer would apparently study her entire body and take photos of her constantly, so much so that Simpson confessed she “worried he was keeping souvenirs before dumping me again.” All I can say is…run away, Jess.
74. The Words Heard Round the World
In 2010, Mayer gave a now-infamous interview with Playboy where he kissed and told. Uh, big time. In the article, he claimed he was addicted to Simpson and waxed poetic about their private bedroom life, calling her “sexual napalm” for the entire world to hear (and remember forever). Simpson’s response was swift and brutal.
75. Final Straw
After the interview, Simpson cut off all contact. “When he reached out to me, I changed my number and changed my email,” she wrote in her memoir. “Delete.” I think I speak for all of us when I say: FINALLY.
76. Lasting Pain
Ever since her tense, horrific relationship with John Mayer, Simpson had been hiding a dark truth. She was suffering from anxiety. To soothe it, she had been self-medicating with alcohol and pills for years, and her addiction made her hit several devastating rock bottoms.
77. The Breakdown Will Be Televised
One of the worst examples of Simpson’s bad habit was her infamous appearance on Ellen in 2017. At the time, audiences were alarmed at Simpson’s behavior. She slurred her words, couldn’t remember how long she had been married for, and generally gave nonsensical answers. Simpson later admitted the whole disturbing story.
In addition to being on other medications, she was drunk at the time. The interview is so embarrassing that Simpson says she can’t watch it to this day.
78. Rise and Shine
At the climax of her addiction, Simpson would start drinking as early as 7 am, and she even had her own special “glittercup” for her drinks.
79. Rock Bottom
It was only a matter of time before it all came crashing down, and on Halloween 2017, Simpson hit her absolute lowest point. After starting at 7:30 am and drinking all day, she not only missed her own Halloween party, she missed something even more important: getting the chance to dress up her kids for their big night.
80. The Road to Recovery
After the Halloween fiasco, she knew something drastic had to change. The very next day, her friends and family staged an intervention for the star, and she agreed to treatment and regular therapy to help herself get better. She hasn’t looked back since.
81. The Lolita Syndrome
With great beauty comes great controversy—as if the case with Brigitte Bardot, cinema darling of the French New Wave. As a model, actress, and singer, Bardot was the European sex symbol from the 1950s to 70s. These days, Bardot continues to make headlines—and pay court fines—for her animal work and her shocking comments about the state of France.
82. Practically Perfect in Every Way, or Else
Bardot was born to a wealthy Catholic family in Paris on September 28, 1934. Her privilege was often dampened by her parents’ conservative moral routine. Bardot wasn’t allowed to choose her own friends and had to refer to her parents in the formal French “vous” as opposed to the familial “tu.”
83. Grandpa Know One When He Sees It
Bardot’s conservative parents were vehemently against her becoming an actress. Ballet and modeling were okay, but acting? It wasn’t a respectable profession for their class. It was Bardot’s grandfather who convinced them to support her efforts, classily explain that “If this little girl is to become a whore, cinema will not be a cause.” Thanks?
84. Half-Baked Plans Go Smooth
Bardot’s relationship with director Roger Vadim was the latest in a long line of disappointments for her parents. The Bardots were vehemently against the match and insisted that Brigitte finish her education in England. It took a suicide attempt on Bardot’s part—she stuck her head in an active oven—to make them budge.
They agreed on the condition that the couple marry when Bardot turned 18.
85. Easy to Replace
In 1967, Bardot and her then-boyfriend Serge Gainsbourg wrote and recorded the notoriously steamy love song, “Je t’aime… moi non plus.” Bardot was married to a powerful man at the time, who refused to let the single be released. Bardot begged Gainsbourg not to let the song out to the public; he consented. The next year, Gainsbourg re-recorded the song with his new girlfriend, Jane Birkin.
This version was an international success. Nevertheless, the version with Bardot made it to public ears in 1986, and was officially released as a download in 2006.
86. Stay in Touch?
According to Bardot, her first marriage to Roger Vadim broke down for a disturbing reason. Bardot claims that Vadim had a number of affairs with men behind her back. For her part, Bardot embarked on an affair with her And God Created Woman co-star, Jean-Louis Trintignant. She and Vadim officially divorced in 1957 after less than five years of marriage.
While they had no children, the two would remain friends and creative collaborators for the rest of her career.
87. Came Back with Something Missing
Although Bardot loves animals, you might not trust her to pet-sit. In 1989, she looked after her neighbor’s pet donkey while he was away…only to castrate the creature without his owner’s consent. The owner took Bardot to court, where she argued the donkey was “sexually harassing” the actress’s own pet donkey and mare. She simply took “things” into her own hands.
88. Happy Birthday, World
For her 40th birthday, Bardot bore it all in a nude photoshoot for Playboy magazine. Talk about a “birthday” suit.
89. Not Everything Mixes Well with the Red
From her retirement to her nude photoshoot, Bardot’s birthday gifts to herself have always been eventful. This one is more tragic: on her 49th birthday in 1983, she was taken to hospital for a stomach pumping after an overdose of sleeping pills or tranquilizers with red wine.
90. Little Girl, Big Potential
Since Lindsay Dee Lohan burst on to the scene as a toddler, she’s been making waves. First, she was the cute little red-headed girl from TV ads, then the Disney drama queen. She matured into the actress with lots of star potential, then became a Hollywood party girl.
91. The Best And The Worst
Lohan says the happiest day of her life was when she got the double lead role as twins Annie and Hallie in The Parent Trap. Her saddest day was the gray day she had to turn herself into jail and see her mom’s disappointed face. Lohan spent 4 out of the 12 days crying, feeling completely shocked at the whole situation.
92. Get by With a Little Help From Friends
While on the set of Scary Movie 5, Lohan and Charlie Sheen forged a friendship. Sheen heard of Lohan’s money woes and wrote her a check for $100,000 to cover her tax debt.
93. Tallying up the Numbers
So how many car crashes has Lohan been involved in? A total of 6 since 2005, as of 2012. The first one was at celebrity favorite The Ivy in Los Angeles. She was found to be at fault and was charged with negligence.
94. It’s Adding Up
How many times has Lohan been arrested and charged? In 2007, she was arrested twice for driving under the influence, and twice again in 2012—in addition to the four times her probation was revoked after she broke the law and managed to skip getting arrested. Oh, she also skipped a court date to go to Cannes, set off her ankle-monitoring bracelet, flunked a drug test and failed to complete community service. She’s also been to rehab five times.
95. Redheaded Jailbird
Lohan has been jailed six times, spending less than a total of two weeks in prison. And she was under house arrest for 35 days, in connection with her necklace theft.
96. Perpetually in Trouble
With all the trouble she’s encountered between her arrests, charges, and more arrests and more charges, Lohan has spent 86% of her adult life on probation.
97. Time for an Intervention
Tina Fey, who wrote and starred in Mean Girls, felt like Lohan was on a downward spiral and took it upon herself to stage an intervention along with Saturday Night Live producer Lorne Micheals and fellow cast members. They pulled her aside and asked her to re-evaluate her party lifestyle, using the tragic deaths of former SNL cast members John Belushi and Chris Farley as examples.
98. Oops She Did It Again
Obviously, Lohan didn’t think she had been in enough trouble, so in 2011 she decided to steal a $5,000 dollar necklace from an LA jewelry store—only a month after leaving rehab at the Betty Ford Clinic. Video footage revealed her wearing the necklace after she denied the theft.
99. Nip It in the Bud
Even though Lindsay Lohan has made the headlines countless times for her drinking and drug abuse, she actually never had a sip of alcohol until she was 17. She says she didn’t like it either, especially after she got really sick in high school because of it. To make matters worse, and to teach her a lesson, Lohan’s mother made her go to bed with dried up vomit still on her clothing.
That ended her drinking right there—she didn’t touch alcohol again throughout high school.
100. Kiss and Tell
While in rehab, Lohan reportedly made a list of every single person she’s ever had sexual relations with. It first got leaked in 2014 and has a few steamy names that were unexpected, like Adam Levine, Colin Farrell, James Franco, and Justin Timberlake—to name a few.
101. Troubled Souls
Lohan and Heath Ledger allegedly had a close bond. The details are blurry, but her diary reveals she was “in love” with Ledger around the time of his tragic death in 2008. On the exact day of his death, Lohan wrote about how he was the love of her life, and how he taught her so much. She goes on to explain that he’s all she’s ever wanted and she wants to hear him laugh and hold her. Lohan’s mother, Dina Lohan, confirms they had been seeing each other around this time.
And in fact, the kiss and tell list above also points to their connection: Heath Ledger is one of the names on the list.
102. From Full House to the Runway
Mary-Kate and Ashley Olsen are a staple when we think of things like Full House and, well, celebrity and style icons. They’ve been in the acting world almost since they came out of the womb and haven’t looked back since. How could they? The twins don’t know anything else. Their lives have played out in front of cameras and TV screens worldwide, both the good and the bad.
They’ve mostly managed to avoid the pitfalls of child stardom, but they have seen their fair share of tragedy and scandal along the way.
103. Too Much, Too Soon
Unfortunately, all of that fame the girls had so early in life took its toll on their parents’ marriage. Their mom initially got them into the entertainment world, but she likely had no idea just how big her daughters would become–and really, how could she? She and the girls’ dad divorced in 1995 as a result of the stress. The whole thing, whether true or exaggerated, played out in The Unauthorized Full House Story.
104. Suffering in Silence
The fame game not only split the family apart with the divorce of the Olsens’ parents, it also went after Mary-Kate’s self-image. It was really first noticed when she was 16 that there was an eating disorder at work, but it would be another two years before she was checked in to rehab for the disease. As far as we can tell, she’s happy and healthy these days.
105. That’s a Secret We’ll Never Know
When police were investigating the circumstances surrounding Heath Ledger’s death, they discovered that the first call that was made after discovering Ledger’s body was to an unlikely source: Mary-Kate Olsen. The pair were allegedly dating and brought her in for questioning. Since Ledger had died of an overdose, the police wanted to know where the illegal substances came from.
Mary-Kate’s lawyer told them she would talk, but only if she was given immunity. As a result, it’s unlikely we’ll ever know the full extent of her connection to his death.