The Derek and Simon Show began life (as many current web shows have) as a rejected TV pilot The Pity Card, which eventually made the rounds as a short film at various film festivals, including Sundance 2006. Young Hollywood actors/sketch performers Derek Waters and Simon Helberg play themselves in a thinly-veined approximation of their nightlife and ineptitude with women.
The episodes, which premiered on TBS’ Super Deluxe comedy site in May of 2007, are produced by their company Type-O and directed by Bob Odenkirk of Mr. Show fame who, being a great fan of the duo, can be held largely responsible for cultivating the project.
“Real-life” best friends Derek Waters and Simon Helberg have a kind of co-dependent relationship, and the show’s episodes are built around a casual conversational approach, like Swingers, and the quasi-documentary style mirrors this premise. While Derek and Simon attempt to project the sensitivity and warmth required of a 21st century male, their confused interpretation of everyday moral and ethical quandries often gets them into predicaments they cannot handle.
Action usually takes place at a bar, karaoke, bowling or wherever girls can be easily approached. Episodes range from bite-sized scenes built around one joke, like a partially-deaf woman mistaken for someone with a overly-cute accent in Baby Talk. However, episodes like Troubled Times parts 1, 2 and 3 follow Derek and Simon in separate A and B storylines. Whatever the circumstances, the two usually end up together at the end of the night, bemoaning their misfortune with girls.
Derek, Simon and Bob Odenkirk also manage to get a few of their famous friends to make appearances. In Sweet Tits, Michael Cera appears as a foul-mouthed, underage bouncer who almost gets his balls crushed by a pissed-off Simon. In the final episode of Troubled Times, Chris Kattan appears as Himself, showing up late to the premiere of Simon’s play, where he succeeds in cockblocking Derek.
The Errand Part 1 (above) and 2 is as epic as this determinedly laid-back series gets. We find Derek and Simon at a Karaoke Club where Simon has gone under false pretenses to sing a duet with a girl. Meanwhile Derek hits on a Scottish backpacker and manages to break all three of his steadfast rules at once. No Karaoke. No Reggae. And never refer to Dave Matthews as Dave.