Guest Stars Brad Leland as Buddy Garrity Scott Porter as Jason Street Kevin Rankin as Herc D.W. Moffett as Joe McCoy Jeremy Sumpter as Joe Doyle "J.D." McCoy Janine Turner as Katie McCoy Zach Roerig as Cash Waller Co Starring Derek Phillips as Billy Riggins Blue Deckert as Mac McGill Drew Waters as Wade Aikmen Anthony Solomon as Charles White Preston Flagg as Daryl Sinqua Walls as Jamarcus Hall Cindy Creekmore as Missy Aubrey Tamara Jolaine as Erin Galen Flemons as Wendell Foley Scott Jefferies as Grant Halbert Armand Anthony as Well Dressed Man James V. Miller as Cab Driver #2 Gary Cherkassky as Hot Dog Vendor Sidekick John Durando as Suit Salesman Hector Arias as Cheap Suit Salesman Rao Rampilla as Cabbie Lainie Frasier as Mrs. Laura Davidson Kristin Malko as Assistant Stephen Gregory Fuller as Booster Credit Only Dana Wheeler-Nicholson as Angela Collette