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| Title | Original Air Date | Guests |
|---|
| 57 | Joshua | January 1 | Tony Bennett, Tom Arnold, Afro-Plane, Kathy Kinney, Ginny, the Dog Who Saves Cats, Paul Gilmartin, Annabelle Gurwitch, John Flansburgh, William, the King of Imagination, Ryah Rosenberg, Sean Medlock |
| 58 | Terminal | August 7 | Dr. Drew Pinsky, Marc Weiner |
| 59 | Toast | August 14 | Merrill Markoe, Adam Carolla |
| 60 | Lawsuit | August 21 | Greta Van Susteren |
| 61 | Cahill | August 28 | Garrett Morris, Mark McEwen |
| 62 | Warren | September 4 | Gary Owens |
| 62 | Warren (short version) | September 6 | Gary Owens |
| 63 | Chinatown | September 11 | Tyra Banks, Rebecca Romijn |
| 64 | Rio Ghosto | September 18 | Ben Stiller, Kevin Smith, Jim Jarmusch |
| 65 | Pal Joey | September 25 | Michael Moore |
| 66 | Curses | November 27 | Moby, Emo Philips, Shirley Manson |
| 67 | Intense Patriotism | December 4 | Jeff Foxworthy |
| Waiting for Edward | December 25 | Denis Leary |
