The Leonard Maltin Game has a been a feature of the Doug Loves Movies podcast since the first episode. However, the game has undergone a number of changes / innovations since the beginning of Season 1. In 101, Doug Benson described the game as something he used to play with Brian Posehn, his first guest. In episode 225, Doug, Posehn, and Sarah Silverman reminisced about playing the game when they were younger.
In Season 1, the game was somewhat different from its current incarnation. It involved finding a movie in the Maltin Movie Guide book, providing the year and a clue about the movie, and then reading the cast list from bottom to top. During this season, Doug usually only had one guest. The non-reading player would try to guess the title as the names were read, and if there were multiple players, as there occasionally were, they would try to guess simultaneously. There was no turn taking or bidding. It was possible to cheat slightly by guessing where in the alphabet the book was open to. Categories were only in use sporadically, and generally for the whole game when used. There were no prizes.
In Season 2, Doug started regularly having more than one guest. In episode 212 (Dana Gould), he introduced his "new twist: We're going to play it Name-that-Tune style" and added bidding and turn taking. Subsequent episodes continued to use the bidding system. Negative bids were not yet part of the system, but you could bid zero names, and say, "Name that movie." In episode 230, Doug started using the Maltin Movie Guide iPhone App, which prevents cheating and makes a lot of other things easier. The app enabled him to start using multiple categories per game. 230 is also the episode where Doug started having panelists play for an audience member, and gave the winner prizes. In episode 241, negative bidding was introduced when Chris Hardwick of Hard & Phirm tried to beat a zero-name bid from Garfunkel & Oates. Over time, Doug started accepting audience-submitted categories, often via Twitter.
In Season 3, episode 301, Doug first suggested the use of audience name-tags to make it unnecessary for him to remember their names, and name-tags were first used in episode 302. In episode 304, Doug first used panelist-provided prizes. In episode 306, Doug suggested the negative-bid rule to Steve Agee, the first time the rule was used by Doug since 241, when the idea was introduced.
Up until Season 5, most of the game categories were fairly straightforward, but during Season 5, gag titles became more and more popular, and by Season 6, most of the categories had gag titles.