Joe rogan
Adam Carolla
Fitzdog Radio- Greg Fitzsimmons' podcast that is a healthy mix of comedy, current politics, philosophy, career talk, etc in a one on one or three person conversation. Check it out.
Pointless- Kevin Pereira's podcast on Joe Rogan's network. Not the best guests yet as its still new, but Kevin is extremely smart and a very natural host, lots of technology and civil liberties discussion.
Comedy Bang Bang- the host interviews his guest, then several comedians come in to improv characters and it generally gets really funny. Very guest dependent.
Smartest Man in the World- Greg Proops in front of a live audience every week. Crazy obscure references, crowd work, liberal politics, and the man can just talk for days and still be entertaining.