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As celebrated as Johnny Depp has been as an actor, his marriages would never win him any trophies. Every one of his girlfriends or wives might have realized how risky living with him was by the time he turned into the world’s most enigmatic method actor by the early 1990s.

All the fun we’ve had watching his bizarre characters over the years have sometimes been marred by the headlines of his volatile relationships. While some actors finally find peace after years of similar turmoil, Depp hasn’t.

His most recent marriage was a disaster of epic proportions. We’re also hearing from both sides about who might have truly been the abusive one. In the meantime, Deep seems to have disappeared into his own world.

Johnny Depp’s earliest relationships

Johnny Depp
Johnny Depp | Junko Kimura/Getty Images

Depp has had an acting career going back more than 32 years, which means some younger fans might not even remember his early dating life. When he was acting on 21 Jump Street in 1987, he’d already had a failed two-year marriage at age 20 to a makeup artist named Lori Ann Allison.

They divorced already in 1985 before Depp was a household name as an actor. During his time on 21 Jump Street, his dating life became the stuff of headlines when he became engaged to Jennifer Grey briefly. After this fizzled out, he also planned to marry Sherilyn Finn.

His private life was fairly stable then, other than one of his first high-profile scuffles in 1989 for assaulting a security guard. Once he left 21 Jump Street, some of his relationships became a little more sustained, outside of almost always ending on sour notes.

Johnny Depp once proposed to Winona Ryder

No doubt Grey and Finn realized had they married Depp, it would have been a mistake due to his volatile lifestyle and long movie shoots. Winona Ryder almost took that plunge herself in 1990 when Depp proposed to her.

You may remember his famous tattoo claiming “Winona Forever,” a word every celebrity today now realizes should never be imprinted on one’s skin. The two did stay together for a while longer, but it inevitably didn’t last. Afterward, Depp changed the tattoo to “Wino Forever.”

Not until 1994 did Depp find a relationship capable of going on for more than just a couple of years. This time it was to supermodel Kate Moss dominating most of the 1990s. Even then, it seemed like Depp always wanted to move on to someone new. Not being easy to live with was also probably due to his noted abuse of alcohol and drugs at times.

Johnny Depp’s long-term relationship with Vanessa Paradis

More maturity helped Depp finally settle down with a mostly successful relationship that was strictly common law. Living with Vanessa Paradis seemed to work, mostly because she was French and it enabled Depp to stay away from the insanity of Hollywood.

During most of the 2000s, most people thought Depp would never return to Hollywood again due to a seemingly blissful life living in France. Having two kids with Paradis also seemed to cool his temperament for a while.

On top of it, Depp was riding high in popularity at the box office during this time, thanks to classics like Pirates of the Caribbean and Finding Neverland. Any analyst of his career can say this was the best time of his life, and something everyone thought would sustain. Not seeing Depp around Hollywood arguably kept him out of trouble and out of the headlines (for the most part).

Johnny Depp’s marriage to Amber Heard

Maybe the first part of this decade had some happiness for Depp beyond his box office popularity starting to slip. Plunging into a marriage with Amber Heard in 2015 seemed like a good bet at the time.

Living in Hollywood again just opened a new can of worms. We all know the back and forth accusations about Heard saying Depp was abusive, and Depp saying vice versa. Whatever the truth is, this piece now ends on a big question mark for Depp’s state of mind and career.