No wonder he’s late, I tell myself; after all, wasn’t he once the 'Leading Actor of the Slacker Generation’, a title he got lumbered with after he made Reality Bites with Winona Ryder back in 1994?And in more recent roles – especially his new film, Brooklyn’s Finest, in which he plays a strung-out cop – there’s a snarlingly uncompromising quality to him.
This one was a bit harder since Winona is so private and rarely publicly discusses her relationships. Tim Burton recalled Depp being distraught over the break up, and many fans consider the two to be soulmates. It was exhausting." Trivia: Upon trying to sex shame Winona, Kay was promptly ridiculed by the public for being unable to keep up with Winona. Page Hamilton (55)Period: 2003Backstory: The two dated quietly for a short period of time before breaking up.
Pete Yorn (41)Period: 2001Backstory: The pair dated briefly until Winona was arrested for shoplifting in 2001.
A reporter for Sassy once asked some alternative rockers if they would go out with her, explaining, "It's my theory that boys start bands so they can get famous enough to attract Winona Ryder." Courtney Love once said, "You're no one in music until you have feuded with me or until you sleep with Winona." In short, Winona had her share of fun. Quote: “We went out for two weeks and he broke my heart, or I thought he did at the time.” (Slater maintains he has no idea what she's talking about)Trivia: Slater continues to think highly of Winona, telling a journalist a couple of years ago he doesn't understand the "she's crazy" party line and that he still loved her. I like Natalie Portman."Trivia: Oberst maintains they were just friends. Jamiroquai/Jay Kay (45)Period: 2003Backstory: The musician from that video that tripped everyone out in the 90s had a fling with Winona and no one would've known about it had he not brought it up years later in a gross, dickhead way.
For this one, I decided to focus on select and notable flames, trying to avoid hearsay. As always, ALL OF THIS IS FROM ARTICLES, SOURCES AND BOOKS. Johnny Depp (52)Period: 1989-93Backstory: The two met at the premiere of Great Balls of Fire! He proposed in 1990 and were engaged for three years before breaking up, allegedly because her father thought she was too young to be wed. Quote: "That was quite a while ago [...] She was very nice and trim down there. She did have this habit of wanting to constantly play hide the sausage.
Quote: "Our relationship is different than any one I've ever had. David Duchovny (55)Period: 1996Backstory: There's nothing to it, it was a fling, although they insist they were just friends. Quote: On the Howard Stern show, Grohl called Winona "a classy lady."Trivia: Their relationship is referenced in the Veruca Salt song Disconnected: "It's kind of scary when your lover leaves you for a movie star."Matt Damon (45)Period: 1997-2000Backstory: The pair were introduced by Ryder's now-former friend Gwyneth Paltrow, who at the time was Damon's BFF's Ben Affleck's girlfriend. They dated for three years and the breakup was, in Matt's words, "far more pedestrian than, say, a mad orgy at the Four Seasons during which my feelings were hurt because Richard Gere was too interested in her." So no drama, it just ended. I'm really lucky that I'm on good terms with him."Trivia: Since their relationship was hounded by rumors of cheating on both sides, Matt was quick to deny reports he was dating co-star Penelope Cruz soon after he and Winona broke up.