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Johnny Depp and Ellen Barkin
Sex symbol Depp was briefly married in the early 1980s before becoming serially engaged to actresses Jennifer Grey, Sherilyn Fenn and Winona Ryder. He later had two successive four-year relationships with Kate Moss and Vanessa Paradis. But in between all that, he briefly dated "The Big Easy" and "Sea of Love" actress Ellen Barkin, nine years his senior, in 1994.