Guest Stars Jason Schwartzman as Greg David Bloom as Kevin Josh Charles as Blake Michaela Watkins as Rhonda Rich Sommer as Graham John Slattery as Claude Dumet 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 Richard Schiff as Dean Fairchild Kerri Kenney-Silver as Real Estate Agent Co Starring Isaak Presley as Kyle Thomas Barbusca as Drew Samm Levine voices Voice of Arty George Dalton as Arty Josh Douglas as Rafi Michael Blaiklock as Danny Hannah Friedman as Becky Hailey Sole as Amy Logan Garretson as Piano Player E.J. Callahan as Elderly Clerk Logistx as Breakdancer John Early as Logan Mark Cirillo as JJ's Friend Peter Salett as Guitar Dude Aisha Hinds as Amelia Kathryn Burns as Dancing Councelor Jeremy Lucas as Singing Counselor #2 Rozzi as Lisa 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