Guest Stars Jay Jackson as Perd Hapley Ben Schwartz as Jean-Ralphio Saperstein Mo Collins as Joan Callamezzo Jon Glaser as Councilman Jeremy Jamm Billy Eichner as Craig Middlebrooks Alan Yang as Chang Andrew Burlinson as Burly Lucy Lawless as Diane Lewis Jenny Slate as Mona-Lisa Saperstein Megan Mullally as Tammy Swanson John Balma as Barney Henry Winkler as Dr. Saperstein Blake Anderson as Mike Bean Ginuwine as Himself Richard Portnow as MItch Savner Joe Souza as Liam Bonneville Jeff Tweedy as Scott Tanner Colin Meloy as Himself Uncredited Jon Hamm as Ed