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Relationships fade, but “wino forever!” Before his rocky marriage and separation with Amber Heard made headlines, Johnny Depp had a slew of high-profile relationships with famous women, including Winona Ryder and Jennifer Grey. During his decades in the spotlight, he’s romanced many of Hollywood’s brightest stars.

Depp’s first marriage was to makeup artist Lori Anne Allison. The pair tied the knot in 1983 and, although their marriage only lasted two years, it led to the Pirates of the Caribbean actor’s big break in Hollywood. As it so happened, Allison’s friendship with Nicolas Cage helped him land his first major acting gig in the 1984 horror classic A Nightmare on Elm Street.

Following the couple’s 1985 divorce, the Sweeney Todd star met Twin Peaks alum Sherilyn Fenn. Though they were reportedly engaged for a time, the pair split after three-and-a-half years together.

Another broken engagement came soon after, when Depp and ‘80s film icon Jennifer Grey called off their relationship shortly after the actor proposed.

And then there was Winona Ryder, of course! After costarring in 1990’s Edward Scissorhands, Depp proposed to the Stranger Things star. Though the pair broke up before they made it down the aisle, part of their iconic relationship lives in infamy: a tattoo on Depp’s arm which once said “Winona forever” and now cheekily reads “wino forever.”

After a few more failed relationships, Depp found his romantic footing with Vanessa Paradis, who he stayed with for 14 years. During their relationship, the pair welcomed two children: Lily-Rose in 1999 and Jack in 2002.

“It wasn’t easy on [Paradis]. It wasn’t easy on me. It wasn’t easy on the kids,” he said in the June 2013 interview. “It doesn’t stop the fact that you care for that person, and they’re the mother of your kids, and you’ll always know each other, and you’re always gonna be in each other’s lives because of those kids. You might as well make the best of it.”

Here’s a look back at the A-lister actor’s most famous — and infamous — relationships.

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Lori Anne Allison

Depp tied the knot for the first time with the makeup artist in 1983. The future superstar was just 20 years old at the time, and Allison was the sister of one of his bandmates. The couple divorced two years later in 1985.

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Sherilyn Fenn

Depp met Fenn on the set of the 1985 student film Dummies. The pair dated for three-and-a-half years, during which time she made an appearance on a 1987 episode of Depp’s TV show 21 Jump Street.

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Jennifer Grey

The Golden Globe nominee popped the question to the Dirty Dancing star in the late ‘80s, but the couple called off the wedding shortly after.

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Winona Ryder

The actor-producer met Winona Ryder for the first time at the premiere for 1989’s Great Balls of Fire! when the actress was only 17. In 1990, they costarred in Edward Scissorhands, and Depp later proposed. More than a decade after they called it quits in 1993, Ryder recalled the end of their relationship in a 2009 interview with Elle UK, calling it her “first real breakup, the first heartbreak.”

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Kate Moss

Fashionable couple! Depp first hooked up with Moss in 1994. During their romance, the Black Mass star was arrested for allegedly trashing a hotel room at the Mark Hotel in New York City. When police entered, they reportedly found the couple sitting amid debris.

“There’s nobody that’s ever really been able to take care of me. Johnny did for a bit,” Moss told Vanity Fair in 2012 of their relationship and subsequent breakup in 1998. “Like if I said, ‘What do I do?,’ he’d tell me. And that’s what I missed when I left. I really lost the gauge of somebody I could trust. Nightmare. Years and years of crying. Oh, the tears!”

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Ellen Barkin

Depp briefly dated Barkin in 1994. The couple made several red carpet appearances during their short-lived relationship. The Animal Kingdom star later claimed that Depp displayed “demanding” and “controlling” behavior during their relationship, calling him “a jealous man” in a November 2019 deposition played during the actor’s defamation trial against Heard three years later.

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Vanessa Paradis

His longest love! Depp and French model, actress and singer Vanessa Paradis were together for 14 years. In 2010, Depp explained to Extra why they never walked down the aisle.

“I never found myself needing that piece of paper,” he said at the time. “Marriage is really from soul to soul, heart to heart. You don’t need somebody to say, okay you’re married. … If Vanessa wanted to get hitched, why not. But the thing is, I’d be so scared of ruining her last name. She’s got such a good last name.”

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Amber Heard

After meeting on set of The Rum Diary in 2009, the pair began dating in 2011. Four years later, they decided to wed days before their planned February 2015 nuptials in the Bahamas.

The Pirates of the Caribbean actor and the Danish Girl actress’ messy split began in 2016 when Heard filed for divorce after 15 months of marriage. The former couple were later caught in the middle of a messy court battle after both sides accused each other of domestic abuse. In June 2022, a jury ruled that Heard had defamed Depp when she published a 2018 op-ed about being a survivor of domestic violence. She was ordered to pay him $10 million in compensatory damages and $5 million in punitive damages. The jury also found that Depp’s attorney defamed Heard in one statement; she was awarded $2 million in compensatory damages.

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Joelle Rich

Us broke the news in September 2022 that Depp started seeing the lawyer who represented him in his U.K. libel lawsuit against The Sun.

“Their chemistry is off the charts. It’s serious between them. They are the real deal,” a source told Us, noting that she is in the middle of a divorce.

While Rich was not part of the legal team who represented the actor in his defamation trial against Heard in 2022, she was in the courtroom to support him: “There was no professional obligation for her being there. It was personal.”