Guest Stars Jason Schwartzman as Greg David Bloom as Kevin Michaela Watkins as Rhonda Josh Charles as Blake John Slattery as Claude Dumet Rich Sommer as Graham Eric Nenninger as Warner Jon Hamm as The Falcon Randall Park as Jeff Kristen Wiig as Courtney Weird Al Yankovic as Jackie Brazen Richard Schiff as Dean Fairchild Rob Huebel as Brodfard Gilroy Kerri Kenney-Silver as Real Estate Agent Co Starring Thomas Barbusca as Drew Isaak Presley as Kyle Samm Levine voices Voice of Arty Josh Douglas as Rafi Michael Blaiklock as Danny George Dalton as Arty Hannah Friedman as Becky Hailey Sole as Amy Logan Garretson as Piano Player Logistx as Breakdancer Mark Cirillo as JJ's Friend Peter Salett as Guitar Dude E.J. Callahan as Elderly Clerk John Early as Logan Aisha Hinds as Amelia Jeremy Lucas as Singing Counselor #2 Rozzi as Lisa Missy Yager as Christine Kathryn Burns as Dancing Councelor Sarah Casolaro as Singing Counselor #1 Kevin Thomas Conroy as Mork Punk Gabriel Millman as Head Punk Christopher Cusumano as Medieval Punk Samuel Goldman as Ventriloquist Counselor Aleksandra Kovacevic as Dummy Counselor Alexandra Moore as Singing Counselor #3 Morgan Parsons as Amy's Friend Madeline Blue as Cure Punk