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| Title | Original Air Date | Guests | |||
| 58 | Terminal | August 6 | Dr. Drew Pinsky, Marc Weiner | ||
| 59 | Toast | August 13 | Merrill Markoe, Adam Carolla | ||
| 60 | Lawsuit | August 20 | Greta Van Susteren | ||
| 61 | Cahill | August 27 | Garrett Morris, Mark McEwen | ||
| 62 | Warren | September 3 | Gary Owens | ||
| 62 | Warren (short version) | September 5 | Gary Owens | ||
| 63 | Chinatown | September 10 | Tyra Banks, Rebecca Romijn | ||
| 64 | Rio Ghosto | September 17 | Ben Stiller, Kevin Smith, Jim Jarmusch | ||
| 65 | Pal Joey | September 24 | Michael Moore | ||
| 66 | Curses | November 26 | Moby, Emo Philips, Shirley Manson | ||
| 67 | Intense Patriotism | December 3 | Jeff Foxworthy | ||
| Waiting for Edward | December 24 | Denis Leary | |||