John Twiller takes down his high school yearbook and begins to reminiscence about that time he first moved into the neighborhood in 1956. His teenage self, Jack is obsessed with Lily one of the more popular girls around. The sole obstacle is Angelo, her bullying boyfriend. With the help of his pals Crutch, Floyd, and Spider, he makes every attempt possible to change her mind.
Michael McKean
as Adult Jack Twiller
Chris Young
as Jack Twiller
Josie Bissett
as Lily
Beau Dremann
as Angelo Gabooch
John Cameron Mitchell
as Floyd
Keith Coogan
as Crutch Kane
Tricia Leigh Fisher
as Gina Gabooch
Danny Nucci
as Spider Bomboni
John Achorn
as Mr. Joe Twiller
Jill Jaress
as Mrs. Kitty Twiller
Lewis Arquette
as Mr. Malloy
Anna Berger
as Mama Gabooch
