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.

One year after their 2012 breakup, he opened up to Rolling Stone about the split.

“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.”

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

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