- 2009: Portrayed Spock's mother Amanda Grayson in J. J. Abrams's "Star Trek"
- 2009: Cast as a newscaster in the "The Informers"; an adaptation of Bret Easton Ellis short stories
- 2008: Re-teamed with "Heathers" screenwriter Daniel Waters for the surreal black comedy "Sex and Death 101"
- 2006: Starred in Richard Linklater's "A Scanner Darkly"; adapted from the novel by Philip K. Dick
- 2002: Spoofed arrest with appearence on "Saturday Night Live" (NBC) and on the cover of W Magazine
- 2002: Acted opposite Adam Sandler in "Mr. Deeds" a loose remake of "Mr. Deeds Goes to Town"
- 2001: Arrested and charged with shoplifiting over $5,500 worth of merchandise from Saks Fifth Avenue in Beverly Hills
- 2000: Received star on the Hollywood Walk of Fame (October)
- 2000: Played a dying woman romanced by a playboy (Richard Gere) in "Autumn in New York"
- 1999: Executive produced and co-starred with Angelina Jolie in "Girl, Interrupted"
- 1998: Acted in Woody Allen's "Celebrity" as an actress/waitress who gets involved with Kenneth Branagh
- 1997: Had first role as an action hero in "Alien Resurrection"
- 1996: Starred opposite Daniel Day-Lewis in "The Crucible" playing his spurned lover who set the witch trials in motion
- 1995: Starred in Jocelyn Moorhouse's "How to Make an American Quilt" opposite Ellen Burstyn and Anne Bancroft
- 1994: Earned a Best Actress Oscar nomination for her portrayal of Jo March in the remake of "Little Women"; produced by Di Novi
- 1994: Made singing debut in Ben Stiller's "Reality Bites"; her involvement as star enabled the project to attract financing
- 1994: TV acting debut, voice-over on "The Simpsons" (Fox)
- 1993: Earned an Oscar nomination as Best Supporting Actress for her performance in Martin Scorsese's "The Age of Innocence"
- 1992: Starred in Coppola's "Bram Stoker's Dracula"; brought Coppola Jim Hart's script, interesting him in the project
- 1990: Co-starred with then-fiance Johnny Depp in Burton's "Edward Scissorhands"; produced by Di Novi
- 1990: Portrayed the meek, religious daughter of a promiscuous mom (Cher) in the coming-of-age drama "Mermaids"
- 1990: Replaced by Coppola's daughter Sofia in the role of Mary Corleone in Francis Ford Coppola's "The Godfather, Part III" after she dropped out due to a respiratory illness
- 1989: Starred in the cult hit "Heathers"; first film with friend Denise Di Novi as producer
- 1989: Played Jerry Lee Lewis' 13-year-old bride (and second cousin) Myra in "Great Balls of Fire!"
- 1988: Took the forgettable "1969" just to get out of her home town of Petaluma
- 1988: Won attention for her supporting role as the Edward Gorey-esque Lydia in Tim Burton's "Beetlejuice"
- 1987: Co-starred with veterans Jason Robards and Jane Alexander in "Square Dance"
- 1986: Film acting debut, "Lucas"; film shot during her eighth-grade summer vacation
- 1985: At age 13, discovered by talent scout Deborah Lucchesi who observed her performing a monologue from her favorite author J.D. Salinger's "Franny & Zooey" at San Francisco's American Conservatory Theatre
- Joined Amnesty International at the age of 12
- Collaborated on a screenplay with "Beetlejuice" co-writer Michael McDowell; script sold but never produced
- Attended San Francisco's prestigious American Conservatory Theatre
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