In Chrysler Classic Racing, players engage in "after-hours" races, starting with an entry-level Chrysler and earning Cool Points by winning races, customizing their vehicles, and enhancing their character's style.

The storyline revolves around the player's journey to become the "King of Cool" by redefining their style and racing prowess in a vibrant 1950s and 1960s setting. Players must navigate the competitive racing scene while upgrading their cars and personal appearance.

Chrysler Classic Racing stands out with its unique blend of racing mechanics and character customization, allowing players to modify classic Chrysler vehicles and their own looks, alongside incorporating mini-games that enhance the overall gameplay experience.