Winona Ryder Main

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This talented actress has graced the screen and entertainment news for the past two decades, thanks to her roles in more than 20 films and her comprehensive dating history, which is probably just as long as her movie credits. Winona Laura Horowitz was born October 29, 1971, in Winona, Minnesota (hence her first name). The daughter of Michael and Cindy Horowitz, hippy, free-spirited parents to say the least, Winona's surroundings and childhood were far from normal.

The Horowitz family relocated to an electricity-free commune in Northern, California, where Winona's siblings (Sunyata, Jubal and Uri) did not have the luxury of television. Young Winona instead watched films at a movie theatre that her mother ran on a barn, and delved into literature. Watching classic films piqued the young girl's interest in becoming an actress, while her fascination with Holden Caulfield, the alienated hero from The Catcher in the Rye, was almost a hint of Winona's childhood and alternative film roles.

When Winona was eight, her parents decided to move back to city-life in Petaluma, California. Thin and tomboyish, Winona was bullied by thugs her first week of school, who mistook her for an effeminate, scrawny boy. This incident led to Winona being home-schooled and eventually studying at the American Conservatory Theater in San Francisco. While performing on the American Conservatory Theater stage, Winona was spotted by talent scouts who wanted her to audition for a role in Desert Bloom, starring legendary actor Jon Voight. She did not get the part, but her tape made its way to Triad Artists. Thanks to the agency, Winona was cast in the 1986 film Lucas.

Though it was not a very successful film, it was a milestone in Winona's career as it was the first time that the actress was credited as Winona Ryder (after a Mitch Ryder album her father owned), at her request. Several forgettable films followed, and Winona finally became recognized after her role in the 1988 Tim Burton comedy, Beetlejuice. Her role as the ghost-friendly, dark teen marked the beginning of a string of dark roles for Winona, all of which she portrayed to a tee.

Heathers, in which Winona plays an equally dark role in an even darker movie, can be considered the favorite film among Winona fans. After her performance in Great Balls of Fire!, Winona teamed up with Tim Burton again in what can be considered one of her most memorable parts, as the love interest of the freak in the off-beat Edward Scissorhands. She starred as Cher's daughter that same year in Mermaids Winona was then on to the next chapter of her life, on to more mature roles and period films. After her role in the independent film, Night on Earth, Winona was cast as what could have been another career defining role -- Michael Corleone's daughter in The Godfather, Part III.

Unfortunately for Winona and the film, the actress had to withdraw from the project due to a respiratory infection. Winona signed with Creative Artists Agency, and found the script for the Francis Ford Coppola vehicle Bram Stoker's Dracula. She approached the legendary director and was cast in the film as the love interest of the bloodsucking count. Winona was all grown up and her career was on the fly. Donning corsets once again, Winona next starred in The Age of Innocence, co-starring Daniel Day Lewis.

Her work garnered her a Best Supporting Actress Oscar nomination. After having returned to modern times as a Gen-Xer in Reality Bites, Winona went back to latter day films, with adaptations of The House of Spirits and Little Women, which garnered her a Best Actress Oscar nomination. She dedicated Little Women to Polly Klaas, a girl from her hometown who was kidnapped and killed.

After roles in the female-bonding flick How to Make an American Quilt; Al Pacino's Looking for Richard; the adaptation of The Crucible; a visit in space with Alien Resurrection; and Woody Allen's star-studded Celebrity co-starring Leo DiCaprio, Famke Janssen and Charlize Theron, Winona starred and acted as executive producer in this year's film adaptation of Girl, Interrupted, co-starring the pouty-lipped Angelina Jolie. Although Winona has been in the Hollywood scene since the mid-80's, she only made her first talk show appearance recently on The Tonight Show with Jay Leno, to promote Girl, Interrupted. She was recently seen co-starring in the tearjerker romance Autumn in New York, co-starring the much-older Richard Gere, and can soon be seen in the thriller Lost Souls.

Named one of People Magazine's 50 Most Beautiful People in the World in 1997, it's safe to say that not only People finds Winona beautiful, considering the long list of boyfriends and flames she has had. The actress had a three-year engagement to Johnny Depp, a long courtship with David Pirner, and has dated Christian Slater, Daniel Day Lewis, David Duchovny, Chris Noth, Matt Damon, and Beck... to name a few. There is more to be said about Winona than her beauty; her wide variety of movie roles, off-screen charm and talent explain her long-term appeal.