The game's storyline takes place between the fifth and sixth seasons and centers on Salvatore "Big Pussy" Bonpensiero's illegitimate son, Joey LaRocca, as he works his way up in the Soprano crime family.

The game begins with Tony Soprano offering Salvatore "Big Pussy" Bonpensiero's son Joey LaRocca (the player character) a place in the Mafia after discovering that he's become a petty thief and punk.

An alternative ending is unlocked should Joey lose all of his respect; the game has a brief scene of him on a boat with Tony and Paulie, asking if he can keep his eyes.

Cast members who reprised their roles from the show include James Gandolfini as Tony Soprano, Michael Imperioli as Christopher Moltisanti, Steven Van Zandt as Silvio Dante, Tony Sirico as Paulie "Walnuts" Gualtieri, Joseph Gannascoli as Vito Spatafore, Vincent Pastore as Salvatore "Big Pussy" Bonpensiero, and Robert Iler as Anthony "A.J."

Other cast members include Monica Keena as Joey's girlfriend Trishelle and Robert Costanzo as Angelo Buscetta of the Philadelphia mob.

Anthony DeSando, who played Brendan Filone on the series, voices an entirely new character as LaRocca's friend and associate, Reggie.

The concept for the game originated from an idea that Sopranos creator David Chase had years earlier in his writing career.

Christian Maelen, who voiced the new player character Joey LaRocca, was reportedly Chase's second choice to play Christopher Moltisanti.