Guest Stars Jason Schwartzman as Greg David Bloom as Kevin John Slattery as Claude Dumet Michaela Watkins as Rhonda Josh Charles as Blake 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 Rob Huebel as Brodfard Gilroy Kerri Kenney-Silver as Real Estate Agent Richard Schiff as Dean Fairchild Co Starring Isaak Presley as Kyle Samm Levine voices Voice of Arty Thomas Barbusca as Drew 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 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 Madeline Blue as Cure Punk 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 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
