I do a ton of driving, so I lean on my podcasts hard. Here are some that I enjoy:

Adam Carolla Show - Adam interviews celebrity guests, complains about everything, and "cracks wise." ~90min/episode.

Adam [Carolla] and Dr. Drew Show - The two best-known former co-hosts of Loveline discuss issues of the day and take sex/drugs/relationship calls ~60 min/episode

Tech411 - Technology news. Geared more towards mobile technology. Hosted by Oscar Santana and Todd Moore (developer of the White Noise app among others). ~30min/episode

Savage Lovecast - Dan Savage from The Stranger takes calls regarding sex/relationship issues. ~45min/episode (free) ~90min/episode (subscription)

The Bugle - Hosted by John Oliver (The Daily Show) and Andy Zaltzman (BBC/Stand-up). Essentially The Daily Show on the "radio," it focuses on a more international news satire. ~45min/episode

Big-O and Dukes Show - Hosted by Oscar Santana and Chad Dukes. A podcast version of their former comedy radio show heard in DC, Phoenix, Iowa, and Baltimore. "Bro" content (beer, video games, movies) for the 20-35 crowd. ~90min/episode

The Mike O'Meara Show - Hosted by Mike O'Meara and Robb Spewak (of Don and Mike Show fame). A podcast version of their former syndicated comedy radio show based in the DC area. Topics of the day discussed, funny audio clips, etc. More of the 30-50 crowd ~60min/episode