Liz's scripted version of Jack and Avery's love story leaves Jack confused and frustrated by his feelings for Diana. Meanwhile, Jenna and Tracy attempt to beat Weird Al Yankovic at his own game, and Kenneth gets an unexpected new job at NBC.
Quest roles:
Jimmy Fallon(Jimmy Fallon), Seth Kirschner(Shawn), Stewart Steinberg(Old Janitor), Sheffield Chastain(Young Dick Lemon), Subhas Ramsaywack(Subhas), Marcella Roy(Young Liz), Mary Steenburgen(Diana Jessup), Cynthia Nixon(Cynthia Nixon), "Weird Al" Yankovic(Weird Al), Billy Baldwin(Lance Drake Mandrell), Chiquinquirá Delgado(Telemundo Anchor), Mike DiGiacinto(Assistant Director)