He made his directorial debut with the mockumentary short film The Dirk Diggler Story (1988), at the age of 18, about a pornographic actor in the 1970s.
Anderson wrote and directed the crime film Hard Eight (1996), starring Philip Baker Hall, John C. Reilly, Gwyneth Paltrow and Samuel L. Jackson.
[7] Anderson directed the romantic comedy-drama Punch-Drunk Love (2002), starring Adam Sandler as a lonely man with anger issues.
Anderson's ninth film, Licorice Pizza, was released to great acclaim in 2021, earning three Academy Award nominations.
He has directed music videos for such artists as Fiona Apple, Haim, Aimee Mann, Joanna Newsom and Radiohead.