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In 2006, Benson began hosting a weekly comedy podcast titled Doug Loves Movies (initially called I Love Movies), which is recorded in front of a live audience in Los Angeles and at clubs all over the U.S. and even in other countries and at sea. The show is archived on iTunes for fans to listen to for free. (There's an occasional premium episode sold for just $2). Benson and guests talk about movies and then play movie related games. Benson's guests have included such notables as John Lithgow, film critic Leonard Maltin, Brian Posehn, Joe Rogan, Zach Galifianakis, Sarah Silverman, Patton Oswalt, Jon Hamm, Adam Carolla, David Cross, Bob Odenkirk, Scott Aukerman, Adam Scott, Bill Simmons, Aziz Ansari, Amy Poehler, Wayne Federman, Elisabeth Shue, Aubrey Plaza, Michael Cera, Edgar Wright, Paul F. Tompkins, T.J. Miller, Kumail Nanjiani, Gillian Jacobs and Michael Sheen.
Regular features of the podcast include the segments “Tweet Relief: Tweets About Movies,” “Watch This/Not That,” “Not for Emetophobes,” and “From the Corrections Department,” as well as the games “Build a Title,” “A-B-C-Deez Nuts,” “How Much Did This Shit Make?” “Doing Lines with Mark Wahlberg,” “Last Man Stanton, " “Whose Tagline Is It, Anyway" "Doug Loves Musicals" and "Jason & Deb's IMDB Game."
In 2010, Benson started hosting an annual 2-hour Twelve Guests of Christmas special every holiday season. This episode features 12 guests (occasionally more) rather than the usual 3-5. This yearly event happens in NYC in addition to Los Angeles.