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Angelina Jolie has constantly been described as one of the most beautiful women in Hollywood ever since her breakthrough role in 1999's "Girl, Interrupted." So it's little surprise that the Academy Award-winning actor has left a trail of heartbreak from those who have fallen under her spell. Jolie has walked down the aisle on three occasions, all to grooms she's previously co-starred with. If that's not all, she's also dated a string of other men and women who are no stranger to the fame game. But how does the Californian fare as an ex-girlfriend?
Well, as you're about to discover, some of Jolie's relationships ended entirely amicably and others ended very acrimoniously. Luckily, for all the showbiz snoops, the majority have been more than happy to discuss the ins and outs with the press. Here's a look at nine who have dished the dirt about their time with Hollywood's most lusted-after lips.
Jonny Lee Miller confirmed he's still friends with Angelina Jolie
Jonny Lee Miller wasn't Angelina Jolie's first significant partner. The "Lara Croft: Tomb Raider" star dated, and even lived with an unknown man, for several years in her teens. But the British celeb was the first to have his name mentioned in public.
The pair first met on the set of 1995 cyber thriller "Hackers" and after a brief separation they decided to get married a year later — Jolie famously sported a white t-shirt emblazoned with Lee Miller's name in blood for the occasion. Perhaps unsurprisingly considering the rather hasty circumstances, the co-stars didn't last the distance and by 1999, they were officially divorced.
However, the pair have remained on good terms ever since, and in 2021, rumors began to surface that the pair's platonic relationship had once again turned romantic, with photos taken of the pair leaving each other's houses on several occasions apparently providing the proof. Lee Miller has largely refused to comment about his connection to Jolie. But in 2017, he did at least confirm one thing in an interview with Stuff: "Yeah — we're still friends. That's all you're getting."
Jenny Shimizu invited Angelina Jolie to her wedding
Angelina Jolie once told Girlfriends magazine that her first walk down the aisle would have been with Jenny Shimizu had her "Hackers" co-star not got there first. The pair became romantically involved during the filming of "Foxfire" in 1996 — the same year that the future Oscar winner wed Jonny Lee Miller. But this wasn't your typical Hollywood love triangle. Shimizu later revealed that Jolie took both herself and Lee Miller to dinner to lay all her feelings out on the table. Of course, in the end, the "Unbroken" director ended up parting company with both by distancing herself from the supermodel and then divorcing her husband in 1999.
Still, just like Lee Miller, Shimizu maintained a civil relationship with Jolie. In 2014, she even offered her an invite to her wedding to brand consultant Michelle Harper. Sadly, the actor declined, much to the bride's disappointment: "It's not like I wanted her to walk me down the aisle or anything," Shimizu later divulged (via Dish Nation). "But it would have been a really cool thing if she'd come."
Elizabeth Mitchell called Angelina Jolie 'a superhero'
Although neither party has ever confirmed that their on-screen relationship spilled over into real life, rumors continue to persist that one-time co-stars Angelina Jolie and Elizabeth Mitchell were once an item.
The pair first met on the set of 1998's "Gia," a biopic of the ill-fated supermodel Gia Carangi, with Jolie playing the titular star and Mitchell her make-up artist and love interest Linda. And whatever happened off set, the former definitely made an impression on the latter. When asked about the Oscar winner by MTV more than a decade later, the "Lost" star replied, "She's a unique and wonderful woman, a superhero."
Mitchell then explained how Jolie was instrumental to her casting: "I got the part because I actually reached out and touched her leg in the audition. Angelina wanted me to get the part because she said I was the only woman who came in and touched her. She and I had a unique situation because we trusted each other immediately and we had an amazing chemistry because we work exactly the same way. We just dove into it. I think it was two young kids who were passionate about acting and having a chance to go for it, and we did. I can't think of a better experience and I love her."
Mick Jagger was scared by Angelina Jolie
In 1997, Angelina Jolie played a stripper in the music video for The Rolling Stones' single, "Anybody Seen My Baby?" And perhaps unsurprisingly, she left the band's famously womanizing lead singer completely smitten.
Mick Jagger was married to Jerry Hall at the time. In fact, the supermodel was pregnant with their fourth child together. But according to reports, that didn't stop the rocker from pursuing Jolie. He allegedly kept calling the star until she caved in to a rather underwhelming meet-up in Florida. Undeterred, Jagger continued to leave various pleading answerphone messages in which, a friend of Jolie's mother claims, he was "virtually sobbing" (via Daily Mail).
The tears must have had an effect as Jolie and Jagger apparently continued to see each other on and off for the next two years. In Christopher Andersen's biography, "Mick: The Wild Life and Mad Genius of Jagger," the latter explained why he was so besotted with the "A Mighty Heart" star: "She scares me a little. I like that."
Billy Bob Thornton believes Angelina Jolie is 'a great person'
Angelina Jolie's eventful love life took another twist at the turn of the century when she exchanged vows with another Hollywood star, Billy Bob Thornton. The pair, who had co-starred in the previous year's "Pushing Tin," had only dated for a couple of months before deciding to marry. Unfortunately, once again, this marriage didn't last long, either.
Yes, the two actors headed for the divorce courts in 2003. But just as she did with first ex-husband Jonny Lee Miller, Jolie remained on good terms with Thornton. Indeed, in an unusually candid 2018 interview with the HFPA, the latter confirmed he had nothing but fond memories of their romance: "That was a great time. Angie is still a friend of mine and she's a great person and she's done so much. She makes movies that are important to her whether they succeed or fail, she still does what she believes in and I'll always respect her for that."
So why exactly did Thornton and Jolie call it quits? Well, the actor claimed that it was their ways of living rather than their personalities that clashed: "Hers is a global lifestyle and mine is an agoraphobic lifestyle. So, that's really — that's the only reason we're probably not still together."
Colin Farrell hailed Angelina Jolie as his 'perfect woman'
Angelina Jolie and Colin Farrell are reported to have become romantically involved with each other during two different time periods. The first was in the mid-'00s while shooting "Alexander," the historical epic in which they played mother and son despite only being a year apart in real life. And the second was in the late '10s in the wake of Jolie's split from Brad Pitt.
Neither party has ever confirmed the rumors, although Farrell certainly fueled things at the London premiere of the movie he later admitted nearly inspired him to quit Hollywood. When asked about his love life while promoting "Alexander," the Irishman said (via FemaleFirst), "I haven't had a girlfriend in a long time but Angie's pretty close to my perfect woman. At the moment I am single but Angelina could well and truly be the right woman. She certainly comes close."
Jolie herself continued the love-in at the same event when asked about being on set with Farrell. She said, "It has been mind-blowing working with him. He's really, really fun to be around. He's full of surprises."
Angelina Jolie rescued Val Kilmer from an icy inferno of solitude
Colin Farrell wasn't the only "Alexander" co-star that Angelina Jolie was reportedly linked to. Val Kilmer, who played King Philip II to her Queen Olympias in the 2004 historical epic, was also rumored to have become romantically involved with the Oscar winner. And he didn't exactly diffuse such talk in his memoir, "I'm Your Huckleberry," published 16 years later.
"I was rescued from an icy inferno of solitude by another angel," was how Kilmer poetically described the nature of his relationship with Jolie before adding, "When people ask me what Angelina is like, I always say she's like other women and other superstars, but just more. More gorgeous. More wise. More tragic. More magic. More grounded. Is it worth it? Worth knowing people who require weeks of effort to understand even a little? Yes."
And the gushing didn't stop there. Kilmer also admitted that he couldn't wait to lock lips with Jolie before they met and even tried to persuade director Oliver Stone to include more sex scenes between their regal characters. He also described the humanitarian, who'd just adopted son Maddox at the time of their apparent courtship, as "the perfect picture of unapproachable stardom and impossibly chic maternal instinct."
Brad Pitt admitted he set Angelina Jolie free
Hollywood got its biggest power couple in 2006 when "Mr. and Mrs. Smith" co-stars Brad Pitt and Angelina Jolie confirmed they were officially together with the news they were expecting a child. The couple then got engaged six years later and in 2014 finally said 'I do.' Sadly, their wedding appeared to have jinxed things.
Indeed, in 2016, the A-listers separated. Three years later they officially divorced. And things have since gotten ugly thanks to lawsuits involving everything from domestic abuse to winery sales. In a 2017 chat with GQ, however, Pitt admitted that he didn't want to split from Jolie: "The first urge is to cling on. And then you've got a cliché: 'If you love someone, set them free.' Now I know what it means, by feeling it."
Pitt also appeared to jinx himself again in the same interview when he claimed he and Jolie were trying to work things their family arrangements out amicably: "I heard one lawyer say, 'No one wins in court — it's just a matter of who gets hurt worse.' And it seems to be true. You spend a year just focused on building a case to prove your point and why you're right and why they're wrong, and it's just an investment in vitriolic hatred. I just refuse. And fortunately, my partner in this agrees." Since then, however, the only comments he's made about Jolie has been through his lawyers.
If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.
Did The Weeknd make Angelina Jolie scream like Neve Campbell?
Few would have put Hollywood glamorpuss-turned-acclaimed director Angelina Jolie and one-time pineapple-haired R&B crooner The Weeknd together. But in 2021, the press went into overdrive with reports that the unlikely pair were dating.
Jolie appeared to sidestep the question when asked explicitly by E! News' Daily Pop about her connection to the man born Abel Makkonen Tesfaye while promoting the superhero film "The Eternals" (via Cosmopolitan). But her rumored beau got everyone's tongues wagging again in early 2022 when he dropped his sixth studio effort "Dawn FM."
Indeed, on the track "Here We Go Again," The Weeknd sings, "My new girl, she a movie star/ I loved her right, make her scream like Neve Campbell/ But when I make her laugh, swear it cures my depressin' thoughts/ 'Cause baby girl, she a movie star." Unsurprisingly, many listeners believed that all this talk of bedroom action with an A-lister was confirmation that he and Jolie really were a thing.
