The Romantic History of Johnny Depp: Winona Ryder, Kate Moss and more

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Relationships fade, but “wino forever!” For his rocky marriage and divorce with Amber heard made headlines, Johnny Dep had a slew of high profile relationships with famous women including winona ryder And Jennifer Grey. During his decades in the spotlight, he has romanticized many of Hollywood’s brightest stars.

Depp’s first marriage was to a makeup artist Lori Anne Allison. The couple tied the knot in 1983 and although their marriage lasted only two years, it led to the pirates of the Caribbean actors big break in Hollywood. Coincidentally, Allison’s friendship with Nicholas Cage helped land him his first major acting gig in the 1984 horror classic A nightmare on Elm Street.

After the couple’s divorce in 1985, the Sweeney Todd meet star Twin Peaks alum Sherilyn Fenn. Although they were reportedly engaged for a while, the couple split after three and a half years together.

Another broken engagement came soon after, as Depp and 80s movie icon Jennifer Gray broke off their relationship shortly after the actor proposed.

And then of course there was Winona Ryder! After costarring in 1990 Edward ScissorhandsDepp introduced to the Stranger things star. Though the pair broke up before coming down the aisle, part of their iconic relationship lives in infamy: a tattoo on Depp’s arm that once said “Winona forever” now cheekily reads “wino forever.”

After a few more failed relationships, Depp found his romantic footing with Vanessa Paradise, with whom he lived for 14 years. During their relationship, the couple welcomed two children: Lily rose in 1999 and Jack in 2002.

A year after their breakup in 2012, he opened up Rolling stone about the split.

“It wasn’t easy [Paradis]. It wasn’t easy for me. It wasn’t easy for the kids,” he said in the June 2013 interview. “You don’t stop caring about that person, and they are the mother of your children, and you will always know each other, and you will being 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.