Anderson started out writing and directing the romantic comedies The Darien Gap (1996), Next Stop Wonderland (1998) and Happy Accidents (2000), all of which premiered at the Sundance Film Festival.

The film became well-known for Bales' dramatic weight loss (62 pounds) for the lead role, and for its screenplay, written by Scott Kosar.

[8] This was followed by Stonehearst Asylum (aka Eliza Graves) in 2014, with Kate Beckinsale, Jim Sturgess, David Thewlis and Ben Kingsley in the leading roles.

[9] In 2018, Anderson directed the espionage thriller Beirut, which stars Jon Hamm and Rosamund Pike,[10] and in 2019, he directed the Netflix thriller film Fractured, starring Sam Worthington, Lily Rabe, Stephen Tobolowsky and Adjoa Andoh, which was released on October 11.

After working together on The Machinist, Anderson and Christian Bale have had plans to collaborate again on an adaptation of J. G. Ballard's novel Concrete Island.

[18] Anderson is slated to direct Peter Dinklage in the title role in an adaptation of Nobel prize winning author Pär Lagerkvist's novel The Dwarf.