Based primarily on the 1995 Nick Hornby novel of the same name, the plot focuses on Rob Gordon, a Brooklyn record shop owner in his thirties obsessed with making top five lists for everything, always observing rather than participating in life.

When his girlfriend Laura leaves him, he goes through a painful re-evaluation of his life and lost loves (with a little help from his music) and he slowly learns that he has to grow up and let go of his self-centered view of the world before he can find real happiness.

Directed by Walter Bobbie, the cast included Will Chase, Jenn Colella, Christian Anderson, Kirsten Wyatt, Rachel Stern, Anne Warren, Emily Swallow, J.B. Wing, and Jay Klaitz.

[3] The show was first produced regionally in 2008 by New Line Theatre in St. Louis, MO, with Jeffrey M. Wright (Rob), Kimi Short (Laura), Zachary Allen Farmer (Barry), Aaron Lawson (Dick), Robb Kennedy (Ian), Nikki Glenn (Liz/Jackie), Margeau Steinau (Marie), Mary Crouch (Charlie), Amanda Densmore (Penny), Patrick Donnigan (Futon Guy), Joel Hackbarth (Klepto-Boy), Andrew Hampton (Hipster/Neil Young), Todd Micali (TMPMITW/Bruce Springsteen), Katie Nestor (Anna/Alison), and Lori White (Sarah); directed by Scott Miller, with scenic design by David Carr and Jeffrey Breckel, lighting design by Michael Bergfeld, and costumes by Amy Kelly.

[4] New Line Theatre brought the show back in 2012 for another successful run, featuring some of the 2008 cast, Jeffrey M. Wright (Rob), Kimi Short (Laura), Zachary Allen Farmer (Barry), Mike Dowdy (Dick), Aaron Allen (Ian), Talichia Noah (Liz), Margeau Baue Steinau (Marie LaSalle), Terrie Carolan (Anna/Alison), Ryan Foizey (Hipster/Neil Young), Nicholas Kelly (Klepto-Boy), Todd Micali (TMPMITW, Bruce Springsteen), Taylor Pietz (Penny), Sarah Porter (Sarah), Keith Thompson (Futon Guy), and Chrissy Young (Charlie); directed by Scott Miller, with choreography by Robin Michelle Berger, costumes by Amy Kelly, lighting design by Kenneth Zinkl, and scenic design by Scott L.