When she was 7 years old, Winona's family repaired to an upscale commune located on a 300-acre plot of land in the northern California town of Elk, where they coexisted with seven other families and a bunch of horses. The kids obviously didn't have televisions (after all, they had no electricity in their homes), but Winona's mother operated a movie theatre in an old barn, where she screened the classic films that provided her enthralled daughter with the key to her future. After a year of living in the sticks, the family moved back to the relative civilization of Petaluma, California. During her first week at her new school, Winona, a fresh-off-the-commune tomboy, was jumped by a gang of pubescent thugs who proceeded to trounce her good for being such an obvious wuss. (''They thought I was a gay boy,'' she has offered by way of explanation.) The unfortunate thrashing yielded fortunate results: Ryder earned a stint of home study, but more importantly, her parents let her enroll in acting classes at the prestigious American Conservatory Theatre in San Francisco, where bullies were few and far between. Talent scouts spotted her on the A.C.T. stage and had her test for the role of Jon Voight's daughter in Desert Bloom. She didn't get the part, but her audition was impressive enough to gain her representation by Triad Artists, which set her up with a role as a poetry-loving teen in Lucas (1986). When the credits rolled, Winona Horowitz officially became Winona Ryder; her new surname was inspired by a Mitch Ryder album belonging to her father.

Ryder's memorable performance in the generally unmemorable film led in turn to a role in the treacly and little-heeded Square Dance (1987); her next role as an anti-war activist in the critically reviled 1969 was certainly nothing to write Petaluma about, either. Ryder's career tide finally turned for the better with Tim Burton's Beetlejuice (1988), in which she played a death-courting, black-garbed teen named Lydia, who understandably has more in common with the ghosts in the attic (Geena Davis and Alec Baldwin) than with her own truly insufferable parents. She again plumbed the darker teenage impulses in the black-as-coal comedy Heathers (1989)—to date, the favorite film of her prodigious career—which had her conspiring with a preternaturally sardonic Christian Slater to murder members of high school cliques and then make the deaths appear to be suicides. That same year, she turned in a fine performance (in a not-so-fine movie) as the 13-year-old bride and first cousin of Jerry Lee Lewis, in Great Balls of Fire! Her next few films flopped, as well, but one thing was becoming certain: Ms. Ryder had the warped teen thang pretty well nailed. For Tim Burton's Edward Scissorhands, she donned an ill-conceived blonde wig to play a more conventional teen—a cheerleader no less—swept up in an unconventional Beauty-and-the-Beast attraction with a bizarre creature played winningly by Ryder's then-fiancé, Johnny Depp. While the film certainly was the most auspicious outing of her career up to that point, the fact remained that Ryder was fed up with playing a teenager, forever poised tremulously on the cusp of maturity.

Independent filmmaker Jim Jarmusch helped bridge the generation gap somewhat by writing a special part for Ryder in his anthology Night on Earth, in which she played an L.A. cabbie who dreams of becoming a mechanic. On the maturity scale, the film was a baby step, to be sure. Ryder would have made a far greater stride in Francis Ford Coppola's The Godfather, Part III, but she was forced to withdraw from the production due to a respiratory infection brought on by exhaustion; her departure from the project led to a particularly unfortunate casting choice of the director's daughter Sofia, an inexperienced and ultimately inept substitute.

Luckily, Ryder and Coppola's dealings were far from completed. After signing with Creative Artists Agency, where she had the foresight to reserve the right to review all scripts submitted to the agency, Ryder latched onto a promising screenplay based on Bram Stoker's novel Dracula. She approached Coppola with the script, and the rest is movie history. Coppola's decadent and erotic Bram Stoker's Dracula provided Ryder with the break she had been looking for: finally, for the first time in her career, she was playing a mature woman, and what's more, the woman in question was the object of the immortal count's blood-soaked desire. Ryder also managed a fairly convincing British accent (the same could not be said for co-star Keanu Reeves), but not everyone was convinced that she pulled the role off. If critics were divided on the ultimate effectiveness of Ryder's performance in the film, they were in absolute agreement over her Oscar-nominated supporting turn as May Welland in The Age of Innocence, a film adapted from Edith Wharton's merciless portrait of 19th-century New York aristocracy.

In 1994, Ryder stepped out of her crinolines to achieve iconic status as the quintessential Gen-Xer in Reality Bites, held her own in a cream-of-the-crop cast in the butchered adaptation of Isabel Allende's The House of the Spirits, and then capped off the year with an Oscar-nominated (this time in the Best Actress contest) performance as Jo March in Little Women. Ryder dedicated the latter film to Polly Klaas, a young girl from Ryder's hometown who was kidnapped and brutally murdered in 1993. (At the time of the crime, Ryder put up a $200,000 reward for information leading to the child's attacker, and she continues to be a strong supporter of the Polly Klaas Foundation.)