IIn 2006, Benson began hosting a weekly comedy podcast, titled Doug Loves Movies (Formerly I Love Movies with Doug Benson), which is recorded in front of a live audience at the Upright Citizens Brigade Theatre in Los Angeles. The show typically tapes weekly, and is later archived on iTunes for fans to listen to for free. Benson and guests talk about movies and comedy both. Benson's guests have included such notables as John Lithgow, 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, Elisabeth Shue, Aubrey Plaza, Michael Cera, Edgar Wright, Paul F. Tompkins, T.J. Miller and Jordan, the baseball-toting superfan.
A regular feature of the podcast is the Leonard Maltin Game, which has been described as Name That Tune with movies instead of songs. The game consists of Benson reading the cast of an unknown movie in reverse order (star of the movie comes last) from Leonard Maltin's Movie Guide to his guests, who attempt to guess the movie.
At the conclusion of many of the early podcasts, Doug would state "As always, Willem Dafoe is a Shithead," which resulted in so many people wondering about why, that Google searches began to automatically complete the phrase as a suggested match. The Willem Dafoe comment started as a joke based on the fact that it would seemingly be the only bad words ever uttered about Dafoe, but many people didn't catch on and, after explaining it a few times, Benson decided to let Dafoe rest. Now, the runners up in the Leonard Maltin game are allowed to name one shithead as a consolation prize.
Benson has also started an annual, 2 hour Twelve Guests of Christmas special every holiday season. This episode features 12 guests rather than the usual 3 and they play an elimination style Leonard Maltin Game. Plans are in the works to bring this yearly event to NYC in addition to Los Angeles.