Derek Waters, Simon Helberg, and Bob Odenkirk first created Derek and Simon in 2005; after meeting with Waters and Helberg, Odenkirk suggested they capitalize on stories from their own lives.
[8][9] Matt Tobey of Comedy Central Insider called The Pity Card "hilariously irreverent".
[10] The series Derek and Simon: The Show was then developed in 2007 for Super Deluxe.
[10] The show follows the exaggerated exploits of 'Simon' and 'Derek', exploring the tragic missteps that the pair encounter as 'outside' forces constantly work against them as they wander through Los Angeles, spending most of their time in bars and chasing women.
Derek Waters and Simon Helberg incorporated guest appearances from many of their comedy friends, including Bob Odenkirk, Richard Dunn, Bill Hader, Sue Foley, Samm Levine, Joe Nunez, June Diane Raphael, Casey Wilson, Marianna Palka, Busy Philipps, Michael Cera, Zach Galifianakis, Jake Johnson, Steve Agee, and Perry Caravello.