yeah, the length is definitely the hardest part about getting people to listen. not only that, but the fact that the show has been on for at least 8 years is also a setback for getting new people to listen. in the case of my room mate, he likes being able to listen to something from the very beginning. he feels like he's missing out if he hasn't heard the whole history of something. now, i know there's the archives, but i got into the show about a year and a half ago, and i still haven't made my way through all of those episodes yet. i really wish that i had known about tbs from the beginning, but i also keep telling him not to worry about it, and that the more he listens to it, the more he'll WANT to look into the archives and get a sense of the history of the show.
a lot of the humor is very inside, and for people who really get tom. i think a lot of people today, if they don't get something RIGHT AWAY, they give up.
that said, i HAVE successfully recruited my girlfriend, and about 5 of our friends, and we now have a kansas city best show listening party every week since like last october. it's easy to get musicians into the show if you give them some good music-based calls or shows to listen to, like barry dworkin, barry levitz, marky ramone, old skull, etc. or play some of the more absurd calls for people at first, like timmy von trimble or pbr or andy from lake newbridge.