Johnny Depp has been linked to actresses and models including Winona Ryder and Kate Moss, and was with Vanessa Paradis for 14 years
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brightcove.createExperiences(); After 15 months of marriage, Johnny Depp and Amber Heard are calling it quits – but this is far from the first breakup the Oscar-nominated actor has weathered.

PEOPLE’s former Sexiest Man Alive, 52, has been linked to a number of actress and models over the years – remember that “Winona forever” tattoo? – and previously went through a divorce and multiple broken engagements.

With Depp’s latest relationship ending after Heard, 30, filed a divorce petition on Monday, here’s a look back at Depp’s rocky romantic history:

Lori Anne Allison
At just 20 years old, Depp married makeup artist Lori Allison, then 25, shortly after moving to Los Angeles to pursue music. While the couple decided to call it quits after two years of marriage, the relationship led to one major connection for Depp. Through Allison’s friend Nicolas Cage, Depp met the agent who landed him his first film role in 1984’s Nightmare on Elm Street, thus launching his wildly successful acting career.

Sherilyn Fenn
Depp and Fenn became romantically linked after meeting on the set of the student film Dummies in 1985. The smitten actor even wrote her name across his helmet in the film Platoon. However, it seems the romantic gesture wasn’t enough to save the relationship. The two were briefly engaged but ultimately split after three years before making it down the aisle.

Though details of their relationship have remained vague over the years, Depp was engaged to the Dirty Dancing star in 1989. The two split after one year together.

“There’s been nothing in my 27 years that’s comparable to the feeling I have with Winona,” Depp told PEOPLE after meeting Ryder at a film premiere in 1990. Five months after their first date, the couple got engaged. As a declaration of his love for the actress, Depp got “Winona Forever” tattooed on his right arm. But like their relationship, the tattoo didn’t last forever. The couple split after three years together, and following the breakup the actor altered the tattoo to read “Wino Forever.”

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Depp met the supermodel at a Manhattan bistro in 1994, and from the beginning their relationship was filled with hard partying and tremendous highs and lows. “They can’t keep their hands, lips, mouths, legs off each other,” a source told PEOPLE at the time. But their passion often turned to intensity, as the couple was frequently seen shouting at each other in public. They called it quits after four years (and a rumored engagement).

Speaking in 2012, Moss said of the relationship: “There’s nobody that’s ever really been able to take care of me. Johnny did for a bit. I believed what he said. Like if I said, ‘What do I do?,’ he’d tell me. And that’s what I missed when I left. I really lost that gauge of somebody I could trust.”

Vanessa Paradis

Depp and Paradis first got together in 1998. Their romance began that June, when Depp saw the French actress sitting with a group of friends at the bar in Paris. Depp had a pal invite her over, and they talked for two hours.

“I could make an endless list of all the things I admire about him,” Paradis said of their romance. “We understand that, if we want our relationship to continue, we must give each other space, allow each other to go off on our own, and trust each other. Not everyone is lucky enough to be given space and trust.”

Though the two never officially tied the knot, the couple have two children together: Lily-Rose and Jack.

Depp and Paradis split in 2012 after 14 years together, with sources telling PEOPLE the two drifted into living separate lives after moving to L.A. from France.