Guest Stars Dave Allen as Jeff Rosso Chauncey Leopardi as Alan White Thomas F. Wilson as Coach Ben Fredricks Ben Foster as Eli Co Starring Busy Philipps as Kim Kelly Steve Bannos as Frank Kowchevski Sarah Hagan as Millie Kentner Natasha Melnick as Cindy Sanders Stephen Lea Sheppard as Harris Trinsky Mark Allan Staubach as Mark Shaun Weiss as Sean Jason Lansing as Ernie Lizzy Caplan as Sara Ron Lester as Seidleman Jarrett Lennon as Colin Marco Gould as Kevin Ashley Power as Popular Girl #1 / #2 Alan Simpson as Tom Brianna Brown as Ashley Kristy Wu as Mousy Girl Stacy Hogue as Karen David Gangler as Don Anna Coman-Hidy as Mousy Girl #2 Gabriel Carpenter as Brett