I especially like Cigar Surgeon's habanos reviews.
Bill Simmons podcasts and the rest of the Channel 33 stuff (especially Keepin' it 1600)
Hardcore History. Dan Carlin is very entertaining.
Local sports radio podcasts (Toucher and Rich, Felger and Mazz)
Soccer pods (Men in Blazers, Football Weekly with James Richardson, BBC Five Live Football and F1, Total Soccer Show)
Stogie Geeks, Cigar Federation, Half Ashed Radio
Tim Goodman's TV Talk Machine