Guest Stars Kyle MacLachlan as Trey MacDougal Vince Vaughn as Keith Travers Carrie Fisher as Herself Hugh Hefner as Himself Sam Seder as Lew Co Starring Jennifer Elise Cox as P.R. Girl Chris Huvane as Waiter Sandra Bentley as Sandy Amanda Bentley as Mandy Amber Collins as Playmate Lisa Mende as Alicia Tara Chocol as Waitress Marty Rackham as Ian Douglas Weston as Realtor Eddie Driscoll as Fendi Man Will Burke as Bellman Uncredited Sasha Perl-Raver as Front Desk Agent