DePaul wrote Saving Silverman, starring Jack Black and Jason Biggs, which was released by Sony Pictures in 2001. The film falls within a cross-genre film type from the late 1990s and early 2000s in which grooms are saved, or nearly saved, from distasteful marriage.[3] It opened at No. 3 at the North American box office making $7.4 million USD in its opening weekend. The film grossed a domestic total of $19,402,030 and $26,086,706 worldwide from a $22 million budget.[4] Killer Bud, was produced independently. It was Robert Stack's final film prior to his death in 2003.
He then wrote Bride Wars, starring Kate Hudson, Anne Hathaway and Candace Bergen. DePaul got the idea when he and his wife were planning a double wedding with her sister.[5][6] In its opening weekend, the film grossed $21,058,173 ranking #2 at the box office.[7] A Chinese remake of the same name was released in 2015.[8]
DePaul's plays and sketch comedy have been performed by The Collective NY, a theatre company in Manhattan.[9] He has performed improv comedy and co-founded Cornfed. DePaul has served on the Board of the Writers and Actors Lab, and co-founded The Clark Street Players.
He wrote the comedy screenwriting manual, Bring the Funny: The Essential Companion for the Comedy Screenwriter.[10] He also led a screenwriting workshop for Harvardwood, a group of Harvard alumni in the entertainment industry, and taught Screenwriting at NYU,[11] The New School,[12] and Savannah College of Art and Design.