Special Guest Stars Jon Hamm as Dr. Drew Baird Meredith Vieira as Herself Guest Stars Bobb'e J. Thompson as Tracy Jr. Calvin Klein as Himself Co Starring Richard Esposito as Richard Esposito Catherine Curtin as Waitress Frank Ridley as Traffic Cop Godfrey as Rick Susan Jeffries as Tennis Woman Chanté Lewis as Woman Uncredited Loukas Papas as Tennis Man