Depp dated Twin Peaks star Sherilyn Fenn in the late '80s after the two met on the set of the 1985 student film, Dummies. The pair later co-starred on a 1987 episode of Depp's TV show, 21 Jump Street. Depp reportedly got engaged to the Shameless actress before eventually calling it quits.
Fenn isn't the only popular '80s star Depp romanced. He also dated Dirty Dancing actress Jennifer Grey in 1989, but they didn't last long.
Depp and Ryder starred in Tim Burton's Edward Scissorhands in 1990, and got engaged that same year. Depp famously got a tattoo reading "Winona Forever" on his arm, which he changed to "Wino Forever" after the two split in 1993.
Ryder, who was 19 years old when they were engaged, called her relationship with Depp her "first real break-up" and her "first heartbreak" in a 2009 interview with Elle magazine.
"And I think it was really ironic because, like, everybody else just thought I had everything in the world, you know, I had no reason to be depressed, everything was sort of at its peak, but inside I was completely lost," the Beetlejuice actress said about dealing with their split at the height of her fame in the '90s.
"I remember feeling, 'I can't complain about anything, because I'm so lucky, I'm so lucky.' After that I realized I needed to take time off more," she continued.
Depp reportedly briefly dated actress Ellen Barkin, nine years his senior, in 1994.
Talk about a gorgeous couple. Depp began dating supermodel Kate Moss in 1994 before splitting four years later.
"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 about their relationship, acknowledging that their breakup was extremely difficult for her. "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," she shared. "I really lost that gauge of somebody I could trust. Nightmare. Years and years of crying. Oh, the tears!"
Depp and model Vanessa Paradis were in a relationship for 14 years before splitting in 2012. The exes have two children together, 16-year-old Chanel model Lily-Rose, and 14-year-old Jack.
"Relationships are very difficult. Especially in the racket that I'm in, because you're constantly away or they're away, and so it's hard," Depp acknowledged in a 2013 Rolling Stone interview. "It wasn't easy on [Paradis]. It wasn't easy on me. It wasn't easy on the kids. So, yeah. The trajectory of that relationship -- you play it out until it goes, one thing leads to another. So for whatever reason that ceases, 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."
Depp and Heard met when they starred in 2011's The Rum Diary, but didn't officially date until 2012, after he split from Paradis. The couple tied the knot in February 2015 with a ceremony on Depp's private island in the Bahamas.
Heard filed for divorce from Depp on Monday, just days after Depp's mother, Betty Sue Palmer, died after a long illness. Heard cited irreconcilable differences in court documents obtained by ET and is asking for spousal support.