Ever since her earliest days in Hollywood, Angelina Jolie’s romantic life has been as fascinating and passionate as her incredible career. Known for being a little rebellious, Angelina has famously defied Hollywood conventions—not only in terms of the roles she chooses but also in her relationships.
From whirlwind marriages with her co-stars to unexpected connections with smash-hit singers, the 49-year-old’s romantic life has been a source of interest for the public for decades.
From her iconic, era-defining relationship with Brad Pitt to her intense marriage to Billy Bob Thornton — which pushed all the boundaries of Hollywood love — join HELLO! as we explore every famous man who has captured the star’s eye (and heart).
Jonny Lee Miller – 1995-1999
Angelina’s habit of marrying her co-stars began with Jonny Lee Miller in 1995; the pair met on the set of the film Hackers, and the sparks flew instantly. They married in a small ceremony in 1996, and Angelina wore Jonny’s name written in her blood on the back of her white shirt on their special day.
Sadly, their intense love didn’t last; they separated after just a year of marriage, thanks to their busy schedules and long-distance love.
Ever the mature couple, Angelina and Jonny only ever had kind things to say about each other since their split and subsequent divorce in 1999. “She is cool as a cucumber. Fearless, that woman,” Jonny told Radio X in February 2024.
Angelina said he was a “solid man and a solid friend”, as per People. It seems this pair has discovered the secret to staying friends with your ex!
Billy Bob Thornton – 2000-2003
Angelina and Billy’s highly publicised love affair began on the set of the 1999 film Pushing Tin when he was still engaged to Jurassic Park’s Laura Dern. The couple eloped to Las Vegas in 2000 and proceeded to make headlines for their swift marriage and 20-year age difference.
Their intense love affair consisted of wearing a vial of each other’s blood around their necks, as well as the eye-catching tattoo Angelina got to honour her husband; the dragon design with his name above it, located on her shoulder, has since been removed and replaced with a list of family birthplace coordinates.
The loved-up couple began the process of adopting Angelina’s first child, Maddox, from Cambodia in 2002, but sadly, they split in 2003, so Angelina completed the adoption on her own. Like Jonny, Billy only had good things to say about his ex-wife, and he told GQ in 2016 that they talk every few months.
As for why their spark fizzled out, Billy said in an interview for HFPA in Conversation in 2018 that it was down to their differing lifestyles. “Hers is a global lifestyle, and mine is an agoraphobic lifestyle,” he said. “So, that’s really– that’s the only reason we’re probably not still together, maybe, because of a different path in life we wanted to take.”
Brad Pitt – 2005-2016
Next came the relationship that stopped the presses: the one and only Brangelina. Again, she met her next husband on the set of their 2004 film Mr and Mrs Smith when Brad was still married to Hollywood darling Jennifer Aniston. Their chemistry jumped off the screen, and the rumor mill went mad when Brad and Jen announced their separation in January 2005.
Just months later, it became clear that Brad and Angelina were more than co-stars when they were photographed together during a trip to Ethiopia, where Angelina adopted her daughter, Zahara.
Over the years, they expanded their family to include six children: Maddox, Pax, Zahara, Shiloh, Knox, and Vivienne, with a mix of adopted and biological children. Their cute family captured the public’s attention and brought them ever closer.
“[Brad] has expanded my life in ways I never imagined. We built a family. He is not just the love of my life, he is my family,” Angelina said in an interview, as per Marie Claire. “I hold that very dear. I suppose what I’ve learned from Brad is to be able to have the kind of family whose happiness and well-being comes before your own. I’m very very grateful to have such a loving family, and I wouldn’t have that without him.”
Brangelina became Hollywood royalty, known not only for their A-list status but also for their humanitarian work. Angelina, a UNHCR Goodwill Ambassador, inspired Brad to become an activist and philanthropist, and together, they visited refugee camps and worked on numerous humanitarian initiatives, like rebuilding homes in New Orleans after Hurricane Katrina.
In 2014, the loved-up pair tied the knot in a private ceremony at their French estate, Château Miraval, but their seemingly perfect marriage came to a shocking end in 2016 when Angelina filed for divorce after an explosive family flight, citing irreconcilable differences. “I am very saddened by this, but what matters most now is the well-being of our kids,” Brad said in a statement. “I kindly ask the press to give them the space they deserve during this challenging time.”
The highly publicised split marked the end of an era and led to messy divorce proceedings, with their assets, including the French estate, being a point of contention between them, as well as custody over their kids.
The Weeknd – 2021-2022
In 2021, Angelina’s unexpected connection with singer The Weeknd (who counts Bella Hadid and Selena Gomez as exes) surprised fans; this couple was not on our bingo cards! The pair were first seen together in July that year on a dinner date; this was quickly followed by another romantic dinner, sparking dating rumours.
The speculation only grew in 2022 when The Weeknd dropped his song “Here We Go… Again”, which included the line: “My new girl, she a movie star.” Fans saw this as a potential nod to the Tomb Raider actress based on their public dates. Although neither of the stars publicly spoke on the rumors, the song sparked widespread speculation about whether the two were more than just friends.
BY KATIE FITZPATRICK
