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

Bobby Daniels

Des

Rod Burke

Raymond

Nate Mooney

Trent

Judy Pryor Trice

Woman in Finery

Jim Fitzpatrick

Rusty

Jim James

Jessie's Band

Two-Tone Tommy

Jessie's Band

Patrick Hallahan

Jessie's Band

Charlie Crowe

Jessie's Band

Carl Broemel

Jessie's Band

Scott Sener

Jessie's Band

John M. Sullivan

Etown Veteran

Sonny King

Etown Veteran

Erwin Russell Marlowe

Etown Veteran

Michael Hatch

Drew at Age 6

Masam Holden

Drew at Age 10

Kelly Pendygraft

Rebecca the Bridesmaid

Jennifer Woods

Bridesmaid

Alana Ball

Maid of Honor

Russell George

Russ from Ernestine and Hazel's

Ralph Conlee

Man on the Bench

Billy Tencza

Brett

Hailey Knight

Isis

Nicky Roos

Sharon's Son

Zane Rice

Little Chapel Boy

Kassie Pinegar

Little Howling Girl

Daya Fernandez

Mercury Shoe Designer

Michael Jaroscak

The Young Recruit

Nigel Miguel

Basketball Coach

Samantha Ray

Frightened Memorial-goer

Nicole Spector

Other Girl in Red Hat

Leslie David Baker

Airport Security #2 (uncredited)

John D. Crawford

Executive Shoe Designer

Joe Koons

Cousin Jimmy (uncredited)