Samurai Champloo: Sidetracked is based on the TV show of the same name, with the characters from the show, Mugen, Jin, and Fuu, along with an unlockable character created exclusively for the game. The main story is the same, the player must embark on a journey in the northern land of Enzo, now present day Hokkaido, in search of a samurai master, but must face perilous foes such as masked assassins, mercenaries, mythic beasts and even gangster monkeys. There is also different endings for each character of the game.
The game has a hip hop feel to it, with the combat engine being connected with the music of the game, choosing different hip hop grooves that will determine the combo that will be used. To use these grooves, players must visit a town's shop, buying records to be taken into battle. Each track contains a certain combination of buttons to be pressed in order to use them, with each record having a unique attack. American voice actors for the dubbed version of the anime show in the states also reprises their voice roles for the game.