O’Brien stars in the improv comedy directed by Matt Walsh. Jimmy, a rebellious teen, tries to keep his neighbour from getting high during a road trip to Oakland. Co-starring James Pumphrey, Abby Elliott, and Rob Riggle. Walsh:
When we cast Dylan – Dylan was the only role we cast – he had no improv experience. I plugged him into [Upright Citizens Brigade], I got him into an intensive for like four weeks … He literally was improvising with the heavyweights of improv as far as I’m concerned. The best people I’ve ever played with – and I’ve done a lot of improv – were in this movie, so he really was challenged to step up his game. He did a great job.