Episodes: Final Season: Chasing It, Season Two: The Happy Wanderer Among the principal cast of The Sopranos is Steven Van Zandt the guitarist with Bruce Springsteens E Street Band. Van Zandt was cast on David Chases love of music despite a limited acting background. Keeping with the tradition of musicians on the show these appearances are much more interesting. The children of Ol Blue Eyes himself Frank Sinatra appeared at separate times as themselves over the series. Frank, Jr. features in Season Two as a card player of the Soprano-run Executive Game. This is also the game where Robert Patrick (the T-1000 of Terminator 2) bets his entire fortune and loses it all. Nancy Sinatra, the singer of such hits as Bang, Bang and These Boots Are Made for Walking appears in the final season at a party for the newly crowned boss of New York Phil Leotardo (Frank Vincent). She even interrupts a heated discussion between Tony and Phil brazenly asking: you two going home with each other? What is confounding is that the children of Sinatra would continue to perpetuate their familys connection to the Mafia. Sinatras Mob connections allegedly coerced a Hollywood producer to cast the singer in an Oscar winning role in From Here to Eternity. This would serve as inspiration in The Godfather.