Angelina Jolie has been a household name in Hollywood for close to three decades. A talented actress and filmmaker, her acting career was launched in 1995 when she landed her first leading role in the film Hackers. After her Academy Award winning performance in 1999’s Girl, Interrupted, Angelina rose to fame and was worshipped as cinema’s hottest bad girl.
As a mother of six, Angie has plenty of familial duties to add to her already hectic schedule. In September of this year, she separated from third-husband Brad Pitt, in a less than amicable split. The famed couple, know as Brangelina during their 12 years together, are no strangers to the tabloids. Despite gracing the covers of gossip mags on the reg, details surrounding their personal relationship have managed to remain somewhat private.
Angelina is a beautiful mess that we love to sink our teeth into. Perhaps, her authentically human side is what we are attracted to. She is not afraid to go a little wild and lose a little control. Let’s take a look at 15 times she shocked mainstream Hollywood with her unrestrained personality.
15. The Time She Hired A Hitman To Kill Her
Angelina has come clean in interviews about her struggles with depression and mental health. In an interview dating back to 2001, a 26-year-old Angie confessed to having contemplated suicide. Afraid of the pain this would cause her family, she instead contacted a hitman to take her out. The hitman was kind to her and told her to think about it for a month before making her final decision. The fog lifted, Angelina found herself in a happier place, and luckily, called off the hit. Interestingly enough, this episode went down while she was married to Billy Bob. It seems to have been a bit of a dark period for both famed actors!
14. The Time She Kissed Her Brother James at The Oscars
So, this was more than a little weird. At the 2000 Oscars, Angelina and her brother were photographed in what appeared to be a non-sibling-style kiss. Family friend Cis Rundle claimed in interviews that the kiss was nothing more than a sister showing love and appreciation for her brother. According to her report, the pair had spent the day in the hospital together, where their mother was receiving cancer treatments. When Angie arrived to the Oscars with her brother as her date, the, uhhh, emotion of the day got to her and she pulled him close for a smooch. To make the scenario even more taboo, she gushed, “I’m so in love with my brother right now!” while making her acceptance speech. A little too weird for our liking.
13. The Time She Married Jonny Lee Miller In Rubber Pants and A Blood-Soaked T-Shirt
Angelina married her first husband, British actor Jonny Lee Miller, just months shy of her 21st birthday. The pair met on set while filming Hackers in 1995. Just 6 months after meeting, the two were wed in a civil ceremony. Angelina wore rubber pants and a T-Shirt with “Jonny Lee Miller” written in her own blood. This girl certainly has an affinity for gore mixed in with romance! “It’s your husband. You’re about to marry him,” Jolie told The New York Times. “You can sacrifice a little to make it really special.” Angie and Jonny were married for 3 years, until they split in 1999. Despite Miller claiming that marriage just didn’t work for them, they do remain close friends to this day.
12. The Time She Wore a Vial of Billy Bob’s Blood Around Her Neck
Remember these two? Angelina and Billy Bob were married for 3 years, from 2000 to 2003. He’s publicly called his marriage to Angelina “a whirlwind” and a time that he’s never been fond of. Nice! The pair, who had a 20-year age gap, were known for their wildly public signs of affection for each other. Lots of PDA, tattoos of each others names and, oh yeah, wearing each others blood! According to Billy Bob, Angie came home one day with a pair of lockets, a razorblades and a very romantic idea. They were both on location filming movies, with very little time together, so Angelina proposed that they wear a vial of each others’ blood. This would keep them close, even if they were geographically far away. Swoon.
11. The Time She Claimed Brad Pitt Was Abusive Towards Their Children to Win Custody
This was a whole new kind of crazy, even for Angelina’s standards. In September 2016, Angelina filed for divorce from Brad Pitt. She alleged that he was unfit to parent their six children, due to anger and dependency issues, and requested sole physical custody of the gang. In the weeks that followed, Angelina stated that Brad had cheated on her, with Russian hookers, and with French actress Marion Cotillard. The embarrassing allegations pushed a (pregnant and married) Cotillard to make a public statement that she had absolutely not had an affair with Pitt. Angelina has been known to smoke out and destroy her enemies…it seems like Brad got unlucky here. The good news? Brad Pitt remained quite calm in the face of a stormy Jolie. He has counter filed for joint custody and (we think) he has enough proof that Angie is a bit nuts.
10. The Time(s) She Took A Lot of Drugs
Angelina is the first to fess up to her murky past involving the consumption of pretty much every drug under the sun. In her early years in Hollywood, she soothed negative feelings with a whole lotta medicine. Estranged from her birth father, Jon Voigt, from a young age, Angelina was the poster girl for “daddy issues”. Despite rekindling a relationship with him years ago, the damage of being raised in a single-parent household left its mark. She has openly discussed how she experimented with drugs in her early teens. This habit grew into a full-fledged love affair. In the late 90’s and early 2000’s, Angelina was consuming cocaine and heroin on a regular basis.
9. The Time She Was Admitted to A Psychiatric Ward for 72 Hours
Back in the Billy Bob days, when Angie was at her peak level of crazy town, she was famously committed to UCLA’s psychiatric ward for 72-hour observation. Admitted shortly before tying the knot with Billy Bob, her near mental breakdown was eerily reminiscent of a scene in her 1999 film Girl, Interrupted. Chalking up the episode to drug-use and stress, Angelina vowed to rid herself of the heroin addiction. She did get clean, shortly before starting the filming for her role in Lara Croft: Tomb Raider began in 2001. Drug use and mental health issues are definitely not a great mix, and we’re glad that Angie found a way to get the heroin out of her system.
8. The Time She Admitted to Self-Harm
By now, it’s no secret that Angelina has a pretty dark side. When she was a tween, she started booking modelling contracts. This early introduction to the superficial side of Hollywood greatly affected her developing self-esteem. Daddy issues and low self-worth combined, and a destructive pattern of self-mutilation was born. Angelina has discussed her early experiences with depression, and how it led to a fixation with sharp objects and self-mutilation. She has talked about how focusing on self-inflicted pain allowed her to release emotions and feel alive when she was struggling with internal demons. Ouch. We hope she has learned new ways to channel her feelings that are less destructive!
7. The Time She Wanted To Be A Funeral Director
Angelina has made quite the career out of acting and directing, but she had a backup plan in case Hollywood didn’t work out: becoming a funeral director. When her grandfather passed away, she was not pleased with the way his funeral was conducted. After that experience, she became interested in helping grieving families’ plan funeral services for their loved ones. She was entirely committed to this career plan, and even completed a mail-order certificate when she was 14 years old. Clearly, her success in cinema has left her with little time to pursue this original mission. Who knows what the future holds?
6. The Times She Appeared in Random Music Videos
Back in the early 90’s, Angelina was an aspiring actress, model and crazy person. As many aspiring stars do, she appeared in a few very random music videos. Thanks to the Internet, you can watch the videos she appeared in to this day. Angie appeared in Meat Loaf’s “Rock N’ Roll Dreams Come True” in 2000, where she plays some sort of missing-person-found-by-Meat-Loaf-and-now-being-serenaded-by-him-amidst-a-background-of-flames. Pretty much sums it up! She’s also featured in an even more horrible video, Lenny Kravitz‘s “Stand By My Woman”. This video is basically Lenny doing a lot of the same arm dance movements in black and white frames, while a gang of 5 women stand next to him and adore him. Weird.. Angelina, why do you agree to these crazy things?!
5. The Time She Had A Wild Relationship With Jenny Shimizu
Angelina met ex-girlfriend Jenny Shimizu on the set of the indie teen drama Foxfire in 1996. She entered into a passionate romance with the fellow actress, claiming that it was a standard case of love at first sight. Angelina has said in interviews that she would have married Shimizu, had she not married first husband Jonny Lee Miller instead. As the story goes, Angelina continued to see Jenny during her marriage to Miller, possibly contributing to the demise of their partnership. If anyone could awake the inner rebellious vixen in Angie, it was Jenny. Their three years of dating were passionate, fiery and far from boring. Angelina divulged intimate details of their sex life in interviews, claiming that Jenny had awoken feelings inside her that she had never felt for in any man.
4. The Time She Hired A Private Detective to Spy on Brad Pitt
Right before filing for divorce this past September, Angelina hired a private eye to spy on hubby Brad Pitt. Not a stranger to intense jealousy and possessiveness, Angelina was convinced that Pitt was having an affair with his gorgeous French co-star, Marion Cotillard. Reps for Cotillard denied the allegations, but Angelina was not convinced. The lack of trust between the partners became evident when news broke that Angie was having him followed. Perhaps she was insecure that he would leave her for a younger, hotter star…kind of like what he did to Jen back in 2004 when he met Angelina.
3. The Time She Told Barbara Walters About Her Sex Life
Ok, I get it. Barbara Walters was sort of the “it girl” interviewer to the stars in her 20/20 days. She provided a platform where they could divulge their juiciest bits of gossip. However, couldn’t you have saved the (then) 75-year old lady the details about your past experience with bondage, rough sex and knife play in the bedroom? Please? No stranger to sharing shocking personal details, Angelina did just that in the 2004 interview. Poor Barb had to sit through Angelina explaining how she had a bloody knife fight during a bondage session that one time (ya, probably more than once).
2. The Time She Blocked Brad Pitt’s Number and Stopped Taking His Calls
OK, another Brad Pitt entry. I’m sorry, it’s just such recent buzz and there is so much wrong with this entire situation! In true toddler fashion, Angie refused to take Brad’s calls, would not agree to a face to face meeting to discuss the children, and even went so far as to block his number. Girl, you were with this man for 12 YEARS. He is BRAD PITT. You have 6 children together. Maybe he pissed you off, we get that. Maybe it’s even for the best that you are splitting. But for the sake of your children, can’t you at least try to suck it up a bit and not be so melodramatic? Due to your craziness, almost the entire planet is now Team-Brad. Way to go!
1. The Time She Tried to Drag Jen Into Her Messy Divorce
So the ultimate crazy award goes to: Angelina trying to drag Jennifer Aniston into her messy divorce. According to sources, Angie wanted her legal team to issue Jen a subpoena and have her admit that Brad Pitt had/has a drug and alcohol dependency in court. Woah! What the heck? You do remember a mere 12 years ago when this woman was married to Brad Pitt? And then you came along and kinda…made it so that he wasn’t married to her anymore? Not only was this crazy, it was pretty inconsiderate. Angelina hit an all time low, even for her standards, when she stooped to this level.