Shannon, a morning show radio host of Louisville, Kentucky, will play for a top prize of $2 million, by trying to outsmart the mob, which includes original "Grease" cast members Jeff Conaway and Susan Buckner, members of the rock 'n' roll band Sha Na Na (Reggie, Donny York, Jocko and Screamin' Scott), as well as "The Apprentice" alumni - - Omarosa, Kelly Perdew and Sean Yazbeck.