Jon Daly had his career beginnings in the 2000s, first appearing in the straight-to-video film 13th Child. In 2004, he made his first big-screen role in the movie Blackballed: The Bobby Dukes Story. He later had roles in the films College Road Trip, Bride Wars, and Mystery Team. Around this period, he also played a recurring role in Parks and Recreation. In the 2010s, he starred in the animated sitcom The Life & Times of Tim, as well as guest-starred in NTSF:SD:SUV:: and Happy Endings. He next starred as Hobbes in the web series Betas. More recently, he starred as Arnie Brown in Showtime’s I’m Dying Up Here. He also portrayed Bill Murray in the film A Futile and Stupid Gesture.