Since the early 2000s, Helberg performed with comedian Derek Waters as the sketch comedy duo Derek & Simon. In 2007, the two starred together in "Derek & Simon: The Show", a web series they created with comedian Bob Odenkirk for the comedy website Super Deluxe. They also made two short films "Derek & Simon: The Pity Card" (co-starring Zach Galifianakis and Bill Hader) and "Derek & Simon: A Bee and a Cigarette" (co-starring Casey Wilson and Emily Rutherfurd) and had a pilot deal with HBO in 2005. One of Helberg's earliest jobs in television was briefly joining the cast of "MADtv" for one season in 2002.