Guest Stars Sarah Gilman as Penny Gill Joel Johnstone as Jack Nikolayevich Sara Amini as Sonya Nikolayevich Patrick Cage as Lamont Moore Joe Gillette as Alan Herskovitz Jordan M. Cox as Richard Ambrose Sloan Co Starring Karen Strassman as Prudence Perlmutter Justin Dray as Derek Smith Ronin Lee as Clarence Mosley Michael Sasaki as Grant Winslow