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

Ted Manson

Sad Joe

Emily Rutherfurd

Cindy Hasboro

Michael Naughton

Another Cousin

Kristin Lindquist

Connie

Allison Munn

Desk Clerk Charlotte

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

Nate Mooney

Trent

Jim Fitzpatrick

Rusty

Jim James

Jessie's Band

Sonny King

Etown Veteran

Masam Holden

Drew at Age 10

Kelly Pendygraft

Rebecca the Bridesmaid

Leslie David Baker

Airport Security #2 (uncredited)