Special Guest Stars Kevin Smith as Duane Anders Guest Stars Michael Muhney as Sheriff Don Lamb David Starzyk as Richard Casablancas Charisma Carpenter as Kendall Casablancas Steve Guttenberg as Woody Goodman Jeffrey D. Sams as Terrence Cook Kristin Dattilo as Carla Cotter Ari Graynor as Jessie Doyle Greg Thirloway as Jeff Cotter Co Starring Brandon Hillock as Deputy Jerry Sacks Valorie Curry as Jane Kuhne Adam Bitterman as David "Curly" Moran Kathleen Parker as Mrs. Stewart Miko Hughes as Stoner Dude #1 Melissa Renée Martin as 09er Girl Lee Ann Kim as Reporter #1 Lindsey Tusing as Beth Erin Noyd as Southie Player #1 Elijah Anderson as 09er Kid Sarah Vincelett as Shelby Lauren Krause as Reporter #2 Amber Ojeda as Cathy Lisa Pedace as Randi Marty Ryan as Bernie Michael Len as Bruno