In 2008, Strauss-Schulson's short film Mano-a-Mano was selected to screen at the South by Southwest Film Festival. The following year, he went back to South by Southwest to premiere his short film Big Pussy, which was subsequently screened at the Just For Laughs Comedy Festival in Montreal, Quebec, Canada. Strauss-Schulson's first feature film, A Very Harold & Kumar 3D Christmas for New Line Cinema and Mandate Pictures, was released by Warner Bros. on November 4, 2011. The film starred Kal Penn, John Cho, Neil Patrick Harris, and Patton Oswalt, and was met with a positive reaction from film critics.