So I'll go ahead and follow up Tom's post and plainly give away where I am on the podcast ladder.
Wait, Wait, Don't Tell Me! - Weekly current events trivia show with sorta-celebrity panelists.
Ask Me Another - Traditional trivia show with weekly VIP's.
Savage Lovecast - Very NSFW show about all things relationship/sexuality related.
RISK - Recordings of live shows, similar to The Moth of people sharing life stories of themselves in precarious situations.
The History of Rome - Self explanatory. Start in 2007, work your way through 2013
Pop Culture Happy Hour - Weekly roundup of whatever is trending in pop culture right now from a variety of viewpoints.
Gilmore Guys - Because I like the Gilmore Girls, okay?!?