2009-05-14 • 22 min
Jack's biological father's health hangs in the balance as the pair start to build a relationship. Liz draws some attention as a relationship expert, despite her own many failed relationships, after an appearance on a talk show. Tracy is invited to speak at his old high school and Kenneth helps him overcome some embarrassing memories from those years.
Cyndi Lauper
Cyndi Lauper
Alan Alda
Milton Greene
Adam Horovitz
Ad-Rock
Mary J. Blige
Mary J. Blige
Clay Aiken
Clay Aiken
Elvis Costello
Elvis Costello
Norah Jones
Norah Jones
Moby
Moby
Michael McDonald
Michael McDonald
Kay Cannon
Wife
Adam Levine
Adam Levine
Talib Kweli
Talib Kweli
Sara Bareilles
Sara Bareilles
Wyclef Jean
Wyclef Jean
Sheryl Crow
Sheryl Crow
Michael Diamond
Mike D.
Rachael Yamagata
Rachel Yamagata
Donald Glover
Gay Kid
Grizz Chapman
Grizz Grizzwold
Sherri Shepherd
Angie Jordan
Napiera Groves
Vontella
Steve Earle
Steve Earle
Rhett Miller
Rhett Miller
Matt Ballinger
White Kid
Capathia Jenkins
Principal
Emalee Burditt
Woman
Helen Coxe
Gay Man's Fiancé
Paula Pell
Paula Hornberger
Sue Galloway
Sue
Chris Parnell
Dr. Leo Spaceman
Kevin Dotcom Brown
Dot Com Slattery
Christine J. Noble
Set Dresser
Robert Randolph
Robert Randolph - He Needs a Kidney Performed by