Turturro has appeared in both comedy and drama films, and engaged in an extended collaboration with the Coen Brothershe appeared in their films "Miller's Crossing" (1990), "Barton Fink" (1991, in the lead role), "The Big Lebowski" (1998), and "O Brother, Where Art Thou?" (2000). Turturro has also appeared in several of Adam Sandler's movies, such as "Mr. Deeds" (2002) and "You Don't Mess with the Zohan" (2008). He played a severely disturbed patient of Jack Nicholson's character in the comedy "Anger Management" and played Johnny Depp's character's antagonist in "Secret Window".