In 2004, he appeared in the film "A Cinderella Story", starring Hilary Duff and Chad Michael Murray. Helberg played the minor role of Simon in George Clooney's 2005 film "Good Night, and Good Luck," where he had one line. In 2005, he had a bit part on "Arrested Development" as Jeff, an employee of the film studio where Maeby worked. From 2006 to 2007, he had a minor supporting role as Alex Dwyer in the drama "Studio 60 on the Sunset Strip." In 2006, he appeared in a series of comical TV commercials for Richard Branson's UK financial services company "Virgin Money." He played a small role in the 2007 film "" as a Jewish record producer.