- 2009: Nominated for the 2008 Academy Award for Best Achievement in Directing (“Milk”)
- 2008: Nominated for the 2008 Directors Guild of America Award for Outstanding Directorial Achievement in Feature Film (“Milk”)
- 2008: Directed a biography of openly gay San Francisco City Supervisor Harvey Milk (played by Sean Penn), titled "Milk"
- 2007: Helmed "Paranoid Park" a film about a teenage skateboarder who accidentally kills a security guard; earned an Independent Spirit Award Nomination for Best Director
- 2005: Helmed "Last Days," based loosely on the final hours of Kurt Cobain
- 2003: Wrote and directed "Elephant", which was inspired by the mass shootings at Columbine High School in April 1999; nominated for an Independent Spirit Award for Best Director
- 2002: Directed "Gerry" which starred and was written by Matt Damon and Casey Affleck; nominated for an Independent Spirit Award for Best Director
- 2000: Directed Sean Connery in "Finding Forrester," about an afro-american teen writing prodigy who finds a mentor in a reclusive author
- 1998: Signed to make a color version of "Psycho" using Joseph Stefano's original script
- 1997: Helmed the mainstream drama "Good Will Hunting"; received first Best Director Academy Award nomination
- 1995: Directed first film he did not write, "To Die For"
- 1995: First film as executive producer, Larry Clark's "Kids"
- 1993: Helmed an adaptation of Tom Robbins' novel "Even Cowgirls Get the Blues"
- 1993: Signed a contract with The Gap to film commercials
- 1992: First directed for TV with the short, "Thanksgiving Prayer," a segment of the PBS compilation special, "American Flash Cards"
- 1991: First original feature film screenplay, "My Own Private Idaho" (also directed)
- 1989: First film with a sizable budget, "Drugstore Cowboy," made for between $4 and $7 million; also first feature in color
- 1985: First widely acclaimed feature, "Mala Noche" (released theatrically 1989); also wrote, edited, produced
- 1983: Returned to Portland, OR to write and direct films, commercials and music videos; also briefly taught film production at the Oregon Art Institute
- 1981: Moved to New York; created commercials for a Madison Avenue advertising firm
- 1978: Received credit for the sound on the comedy film, "Property"
- 1976: Worked as an assistant to Ken Shapiro ("Groove Tube"), working on comedy scripts
- 1968: As an art student, discovered the work of Andy Warhol; inspired to start making films
- 1967: Had a summer advertising job on NYC's Madison Ave at age 16
- Family moved to Portland, OR when Van Sant was 17
- Shot his first painterly, animated films with an 8 millimeter Kodak
- Moved back in with parents back in Darien, CT and worked for his father in a New Jersey warehouse
- Short film, "The Discipline of D.E." debuted at the New York Film Festival
- Moved extensively around the country with his parents as a child before settling in Darien, CT
- Collaborated with future cinematographer Eric Edwards on the high-school film project, "The Happy Organ"
- Feature film directing debut, "Alice in Hollywood," an attempted screwball comedy that was never released
- Made rare TV appearance interviewed by film critic Charles Champlin on "Champlin on Film" on Bravo




