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 Mary J. Blige as Herself Cyndi Lauper as Herself Adam Levine as Himself Sheryl Crow as Herself Sara Bareilles as Herself Elvis Costello as Himself Clay Aiken as Himself Wyclef Jean as Himself Napiera Groves as Vontella Michael McDonald as Himself Ad-Rock as Himself Mike D as Himself Moby as Himself Norah Jones as Herself Robert Randolph as Himself Rachael Yamagata as Herself Talib Kweli 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