Special Guest Stars Sherri Shepherd as Angie Jordan Alan Alda as Milton Greene Guest Stars Chris Parnell as Dr. Leo Spaceman Steve Earle as Himself Cyndi Lauper as Herself Mary J. Blige as Herself Adam Levine as Himself Sheryl Crow as Herself Sara Bareilles as Herself Elvis Costello as Himself Napiera Groves as Vontella Moby as Himself Ad-Rock as Himself Michael McDonald as Himself Mike D as Himself Norah Jones as Herself Clay Aiken as Himself Robert Randolph as Himself Rachael Yamagata as Herself Talib Kweli as Himself Wyclef Jean as Himself Rhett Miller as Himself Co Starring Sue Galloway as Sue LaRoche-Van der Hout Paula Pell as Paula Hornberger Donald Glover as Gay Kid Matt Ballinger as White Kid Bobby Blanski as Handsome Fiancé Emalee Burditt as Woman Helen Coxe as Gay Man's Fiancé Capathia Jenkins as Principal Kay Cannon as Young Woman Uncredited Julia Murney as Courtney