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