In Keeping the Faith (2000), Norton not only directed but also starred alongside Ben Stiller and Jenna Elfman in a romantic comedy with a twist. The film explored the dynamics between a Catholic priest, a Jewish rabbi, and a childhood friend who returns to their neighborhood. Norton's direction balanced humor with emotional depth, while his casting choices brought authenticity to the complex relationships depicted on screen.
However, it was Motherless Brooklyn (2019) that truly demonstrated Norton's fearless approach to filmmaking. Adapted from Jonathan Lethem’s novel, the film follows Lionel Essrog, a detective with Tourette syndrome, as he uncovers a web of corruption in 1950s New York. Norton's decision to take on such a complex character, both as an actor and a director, underscores his dedication to pushing creative boundaries. His casting selections, including Willem Dafoe and Alec Baldwin, added layers of depth to the story, making Motherless Brooklyn a testament to his talent for handling difficult and nuanced subject matters in his directorial endeavors.