"Crashing" came first focusing on the semi-fictional life of comic Pete Holmes and was developed by Judd Apatow. This anti-sitcom is based around Holmes' actual stand up, which if I'm being honest I never found all that funny. This show however is hilarious, tragic, but hilarious.
Propelled by recurring guest stars like Artie Lange, T.J. Miller, and Sarah Silverman, it begins when Holmes' wife cheats on him and after leaving her, he begins to take his stand up career seriously while couch surfing with friends and strangers. The tragedy of his life is countered by how funny the situations he finds himself in. I loved it and hope it returns for a second season.
Both series offer intriguing insight on the industry, from two completely different eras, and both worth checking out.