In Chrysler Classic Racing, the player races classic Chrysler cars on various tracks. The main portion of the game is found in the story mode, where the player selects from one of four nerds, and after seeing a cool person driving a Chrysler car, decides to race to the top and become cool themselves.[2] The car selection features Chrysler cars from the 1950s through the 1970s.[1] Races mostly feature standard Wii controls, and require use of the Wii Remote nunchuk attachment.[2] The Nintendo DS version uses the D-Pad and not the touch screen in order to control movement.[5] Once a player has completed a track in story mode, they can then replay the track as many times as they want to outside the story mode; the game allows the player to set a "mirror mode", which reverses the track to give the player a new experience.[2]
After completing races, players must play one of three different minigames: "Be my Baby", "Gauntlet Challenges", and "Kings Challenges".[2] In "Be my Baby", the player must collect teddy bears from a top-down perspective in order to impress women, while in the other two challenges, the player must race rivals in order to collect cool points and cash.[2]