Orlando Bloom

Drew Baylor

Kirsten Dunst

Claire Colburn

Susan Sarandon

Hollie Baylor

Alec Baldwin

Phil DeVoss

Bruce McGill

Bill Banyon

Judy Greer

Heather Baylor

Jessica Biel

Ellen Kishmore

Paul Schneider

Jessie Baylor

Loudon Wainwright III

Uncle Dale

Gailard Sartain

Charles Dean

Jed Rees

Chuck Hasboro

Paula Deen

Aunt Dora

Dan Biggers

Uncle Roy

Alice Marie Crowe

Aunt Lena

Tim Devitt

Mitch Baylor

Ted Manson

Sad Joe

Maxwell Moss Steen

Samson

Reid Thompson Steen

Samson

Shane Lyons

Starstruck Kid

Emily Rutherfurd

Cindy Hasboro

Michael Naughton

Another Cousin

Griffin Grabow

Griffin

Nina Jefferies

Staring Mona

Emily Goldwyn

Star Basketball Player

Kristin Lindquist

Connie

Allison Munn

Desk Clerk Charlotte

Tom Humbarger

Crematory Concierge

Patty Griffin

Sharon

Gregory North

Helicopter Pilot

Steve Seagren

Dock Worker

Guy Stevenson

Security Guard

Jeffrey De Serrano

Security Guard

Jeanette O'Connor

Assistant

Catherine McGoohan

Assistant

Sean Nepita

Mike Bohannon

Dena DeCola

Debbie

David Brandt

Hotel Manager

Jenny Gregg Stewart

Loud Kid

Delaney Keefe

Loud Kid

Travis Howard

Electrician

Masam Holden

Drew at Age 10

Joe Koons

Cousin Jimmy (uncredited)