A while back I discovered a web series called The Guild.
"The Guild is a independent sitcom web series about a group of online gamers. The show started in the late summer of 2007, and for the first season was financed solely by Paypal donations from LOYAL FANS. Since season 2, The Guild has been distributed by Xbox Live and Microsoft and sponsored by Sprint.
Episodes vary from 3-8 minutes in length, and follow the Guild members’ lives online and offline.
“The Guild” has won numerous awards, including the SXSW, YouTube and Yahoo Web Series Awards in 2008, and 3 Streamy Awards in 2009: Best Comedy Web Series, Best Ensemble, and Best Actress for Felicia Day." http://www.watchtheguild.com/
All the episodes are avilable on MSN video or Xbox
To get ya started here's the first episode:
And one of their music videos: