In 1976 Jackson moved to New York City and began working in the theatre there. In 1981, while appearing in Charles Fuller’s Pulitzer Prize-winning A Soldier’s Play, Jackson met actor Morgan Freeman and aspiring film student Spike Lee. Both offered Jackson encouragement, and Lee cast Jackson in some of his early films, including School Daze (1988), Do the Right Thing (1989), Mo’ Better Blues (1990), and Jungle Fever (1991), for which Jackson garnered the first best supporting actor award ever bestowed by the Cannes film festival judges for his riveting performance as a hard-core drug addict. That role prompted Jackson, who had just come out of rehab, to permanently end his own personal drug addiction.
Jackson’s breakthrough came in Tarantino’s cult classic Pulp Fiction, in which Jackson portrayed a loquacious Bible-verse-spewing killer. For that part he earned an Academy Award nomination for best supporting actor. His other credits in the 1990s included Jurassic Park (1993), Die Hard with a Vengeance (1995), A Time to Kill (1996), The Long Kiss Goodnight (1996), Tarantino’s Jackie Brown (1997), The Negotiator (1998), and Star Wars: Episode I—The Phantom Menace (1999), as Mace Windu. He reprised that role in Star Wars: Episode II—Attack of the Clones (2002) and Star Wars: Episode III—Revenge of the Sith (2005). In addition, he provided the voice of that character in Star Wars: Episode IX—The Rise of Skywalker (2019).
In the 21st century Jackson showed his versatility, appearing as a colonel in the military in Rules of Engagement (2000), a police detective in John Singleton’s blaxploitation movie remake Shaft (2000), an angry motorist in Changing Lanes (2002), an FBI agent in Snakes on a Plane (2006), and an outspoken but devoted white slaver’s butler in Tarantino’s blood-drenched Django Unchained (2012). After Jackson allowed Marvel Comics to use his features for the character Nick Fury, he signed (2009) a nine-movie deal that included Iron Man 2 (2010), Captain America: The First Avenger (2011), The Avengers (2012), Captain America: The Winter Soldier (2014), Avengers: Age of Ultron (2015), Spider-Man: Far from Home (2019), and Avengers: Endgame (2019).In 2015 Jackson gained accolades for his roles in Lee’s Chi-Raq, a satire on gang violence in Chicago, and Tarantino’s The Hateful Eight, in which Jackson starred as a Black bounty hunter encountering racism and extreme violence in the aftermath of the American Civil War. The following year he starred as a villain seeking immortality in Tim Burton’s Miss Peregrine’s Home for Peculiar Children, a fantastical adventure based on a popular young adult series by Ransom Riggs. Jackson’s films in 2017 included Kong: Skull Island and The Hitman’s Bodyguard; in 2021 he appeared in the latter’s sequel, The Hitman’s Wife’s Bodyguard.
In addition, Jackson was involved in several Broadway productions. In 1990–91 he was an understudy in August Wilson’s The Piano Lesson, and he later played Martin Luther King, Jr., in The Mountaintop (2011–12). In 2022 he had a lead role in a revival of The Piano Lesson; it was directed by his wife, LaTanya Richardson Jackson.