Upon learning the troupe responsible for the show, Ultimate Improv, was offering paid workshops to foot the bill for their theater space, Dan decided to take the plunge and sign-up.

During his time with Boom Chicago, Dan co-wrote and performed in one of the troupe's biggest hit shows to date: "Me, MySpace and iPod".

[4] Between major productions, Oster found himself trying a bit of everything by way of his fearless stage persona, from jokingly discussing penile inadequacy to performing freestyle raps as obscure pop culture icons like Paul Reiser and Cobra Commander from G.I.

Outside the Boom theater, one of Dan's most noteworthy pre-MADtv gigs came in the form of a 30-minute mockumentary-style television program entitled "The Digital Difference".

The cast includes Oster himself as well as Jen Burton, Laurel Coppock, Lauren Flans, Will Maier, and Bobby Mort.