Ryder's unconventional upbringing certainly contributed to the startling intelligence and self-possession behind those wide-set eyes. Born Winona Horowitz to two hippies thoroughly "into the pudding", she grew up surrounded by some of the brightest lights of the counterculture. Timothy Leary was her godfather (her father Michael Horowitz disavows any involvement with the acid guru's 1970 prison breakout, giving full credit to the radical Weathermen), and Allen Ginsberg often dropped by the Mendocino commune where she lived for four years enjoying a life without TV (without electricity!) that turned her onto books. Money was scarce, but love was in abundance. Yet when the family finally settled in Petaluma, California, she discovered that her years "on the bus" set her apart from her peers, and this experience as a "suburban reject" would help inform some of her best work from "Beetlejuice" (1988) to "Girl, Interrupted" (1999). Her parents promptly curtailed the public school experiment and to add spice to her home study program enrolled her in acting classes at San Francisco's American Conservatory Theatre.

Spotted there by a talent scout and screen tested for a role in "Desert Bloom" (1986), Ryder lost out to Annabeth Gish, but her audition tape found its way to director David Seltzer who cast her in the underrated "Lucas". The following year she played a Texas teenager torn between her grandfather (Jason Robards) and her mother (Jane Alexander) in "Square Dance" and walked away with the best reviews, setting the stage for her first collaboration with Burton, "Beetlejuice" (1988). Ryder nailed her supporting role as a morose teen with a penchant for black clothing who is thoroughly alienated from her suburban parents, and nearly stole the film from co-stars Michael Keaton, Alec Baldwin and Geena Davis with her low-key, perfectly deadpan vocal delivery. Further solidifying her reputation as a queen of teen angst with "Heathers", she deftly negotiated the complex terrain as her character advanced from passive hanger-on to murderer with a conscience, all the while retaining the audience's affection. Excellent as the child bride of rock idol Jerry Lee Lewis (Dennis Quaid) in "Great Balls of Fire!" (1989), she was the sole bright spot as the offbeat but intelligent Dinky in the uneven "Welcome Home, Roxy Carmichael" (1990).

Reteaming with Burton, Ryder (despite an ill-advised long blonde wig) delivered a naturalistic portrait of a young woman at first repulsed then later drawn to the freakish but gentle "Edward Scissorhands" (1990). Although the director did not depict her as thoroughly disaffected, he certainly took ample shots himself at the cookie-cutter conformity of suburban existence. Rounding out the year as Cher's eldest daughter in "Mermaids", Ryder played a neurotic Jewish girl who wants to become a nun to escape the unconventional lifestyle of her mother, receiving the film's best notices and picking up her first acting award from the National Board of Review. Though illness reportedly had forced her out of the pivotal role of Mary Corleone in Francis Ford Coppola's "The Godfather, Part III" (1990), she got her chance to work with the director on "Bram Stoker's Dracula" (1992). Her pale, sylph-like beauty was perfect for the period piece, and Ryder provided the film's emotional core without being overshadowed by the film's phantasmagoric special effects, lavish production design and showier co-stars.

Martin Scorsese tapped her for another period piece, his remake of "The Age of Innocence" (1993), and Ryder built on the air of sophistication developed opposite Anthony Hopkins in "Dracula", swooshing around in hooped dresses and showing some affinity for the admittedly uncomfortable bustle. "You can't breathe too well," she told journalist Roger D Friedman. "But when you're that restricted, it makes your performance more accurate. The etiquette and dialect, the detail of the costumes and sets. It makes you feel like you exist in that time." The actress earned her first Oscar nomination as Best Supporting Actress portraying the demure yet strong-willed May Welland whose fiance (Daniel Day-Lewis) has fallen in love with her cousin (Michelle Pfeiffer). Ben Stiller's "Reality Bites" (1994) offered her the chance to lose the bustle and don jeans as a Gen-X heroine forced to choose between a slacker boyfriend (Ethan Hawke) and a neurotic workaholic (Stiller). Though the promising and eccentric tale of contemporary youth devolved into a banal love story, Ryder acquitted herself well in the relatively thankless role, overshadowing her co-stars and earning critical praise for her work.

Ryder stepped back into period garb for Gillian Armstrong's outstanding remake of "Little Women" (also 1994), and curious parallels between herself and the headstrong, bookish Jo March (an autobiographical representation of the novel's author Louisa May Alcott) made her an ideal candidate to play the 19th Century heroine. Both had grown up in a close family that lived in a house with no electricity or running water, and the utopian Brook Farm, the transcendentalist settlement that Alcott's father Bronson helped establish, bore more than a passing resemblance to the Mendocino commune of Ryder's youth. As ringleader of the spirited "Little Women", she delivered a strong performance in what is arguably the best screen rendition of the novel, garnering her second Oscar nomination (this time as Best Actress). She went on to essay a graduate student who learns about life and love in "How to Make an American Quilt" (1995) and tried her hand at Shakespeare with a turn as Lady Anne in Al Pacino's award-winning documentary "Looking for Richard" (1996).

Again cast opposite Day-Lewis in the film version of Arthur Miller's "The Crucible" (also 1996), Ryder proved her mettle as the unsympathetic Abigail, a scorned woman who seeks revenge by fabricating tales of witchcraft. Attempting to stretch as a performer, she took on her first action-adventure role, teaming with a clone of Ripley (Sigourney Weaver) to battle the monsters of the "Alien" franchise's fourth installment, "Alien Resurrection" (1997), then stayed on the sidelines for the next two years except for a small but luminous role in Woody Allen's "Celebrity" (1998). When she next turned up it was as executive producer and star of "Girl, Interrupted" (1999), based on Susanna Kaysen's memoir of her experience at a mental hospital in the 60s. Drawing on her own brief commitment in the early 90s, Ryder rose above the script's limitations to credibly render the rich, spoiled and confused 17-year-old, though Angelina Jolie trumped her as the irrepressible sociopath more responsible for Susanna's rehabilitation than the doctors. The following year saw her star in the exorcism thriller "Lost Souls" (the feature directorial debut of cinematographer Janusz Kaminski) and "Autumn in New York", in which she played a dying woman romanced by a playboy (Richard Gere) under the guidance of director Joan Chen. The film garnered few critical thumbs-up and even fewer ticket sales.

By the end of 2001, it appeared that Winona Ryder had lost some of her ability to generate big box office revenues. However, she also proved that she had not lost her ability to generate headlines: On Dec. 12, 2001, the actress was detained by security employees at the Saks Fifth Avenue department store in Beverly Hills after she had been captured on videotape and observed by security guards shoplifting nearly $6,000 worth of the swanky store's high-end merchandise, cutting off sensor tags and secreting the items in shopping bags. Her subsequent arrest and court case captured the attention of the media-both mainstream and tabloid-who were soon watching her every move and clamoring for seats to attend her Beverly Hills hearings. Denying all the charges, Ryder spoofed her arrest while out on bail awaiting her day in court, appearing on the late-night sketch comedy series "Saturday Night Live" (with the tag line "She'll steal your heart") and posing for the cover of W magazine wearing a "Free Winona" t-shirt, an item that became trendy during her shoplifting saga. Meanwhile, two films featuring the actress, the Adam Sandler comedy "Mr. Deeds" and the CGI-inspired Hollywood morality fable "Simone," came and went at the box office with much fanfare but lukewarm grosses. Ryder's trial commenced on Oct. 24, 2002, and in a strange quirk of fate one of the jurors was producer Peter Guber, a former studio head who gave the greenlight to three films starring Ryder ("Dracula," "The Age of Innocence" and "Little Women") while he was the co-head of Sony Studios in the early 1990s. The actress' attorney argued that Ryder had bought several items prior to her arrest and instructed a salesperson to keep her account open (no evidence that she had such an arrangement was presented); further, he argued that Saks employees had targeted the actress in hopes of selling the story of her arrest. Prosecutors successfully refuted the conspiracy claims and on Nov. 6, 2002, Ryder was convicted of two of the three charges against her: theft and vandalism.