Orlando Bloom

Character: Drew Baylor

Kirsten Dunst

Character: Claire Colburn

Susan Sarandon

Character: Hollie Baylor

Alec Baldwin

Character: Phil DeVoss

Bruce McGill

Character: Bill Banyon

Judy Greer

Character: Heather Baylor

Jessica Biel

Character: Ellen Kishmore

Paul Schneider

Character: Jessie Baylor

Loudon Wainwright III

Character: Uncle Dale

Gailard Sartain

Character: Charles Dean

Jed Rees

Character: Chuck Hasboro

Paula Deen

Character: Aunt Dora

Dan Biggers

Character: Uncle Roy

Alice Marie Crowe

Character: Aunt Lena

Tim Devitt

Character: Mitch Baylor

Ted Manson

Character: Sad Joe

Maxwell Moss Steen

Character: Samson

Reid Thompson Steen

Character: Samson

Shane Lyons

Character: Starstruck Kid

Emily Rutherfurd

Character: Cindy Hasboro

Michael Naughton

Character: Another Cousin

Griffin Grabow

Character: Griffin

Nina Jefferies

Character: Staring Mona

Emily Goldwyn

Character: Star Basketball Player

Kristin Lindquist

Character: Connie

Allison Munn

Character: Desk Clerk Charlotte

Tom Humbarger

Character: Crematory Concierge

Patty Griffin

Character: Sharon

Gregory North

Character: Helicopter Pilot

Steve Seagren

Character: Dock Worker

Guy Stevenson

Character: Security Guard

Jeffrey De Serrano

Character: Security Guard

Jeanette O'Connor

Character: Assistant

Catherine McGoohan

Character: Assistant

Sean Nepita

Character: Mike Bohannon

Dena DeCola

Character: Debbie

David Brandt

Character: Hotel Manager

Jenny Gregg Stewart

Character: Loud Kid

Delaney Keefe

Character: Loud Kid

Travis Howard

Character: Electrician

Bobby Daniels

Character: Des

Rod Burke

Character: Raymond

Nate Mooney

Character: Trent

Judy Pryor Trice

Character: Woman in Finery

Jim Fitzpatrick

Character: Rusty

Jim James

Character: Jessie's Band

Two-Tone Tommy

Character: Jessie's Band

Patrick Hallahan

Character: Jessie's Band

Charlie Crowe

Character: Jessie's Band

Carl Broemel

Character: Jessie's Band

Scott Sener

Character: Jessie's Band

John M. Sullivan

Character: Etown Veteran

Sonny King

Character: Etown Veteran

Erwin Russell Marlowe

Character: Etown Veteran

Michael Hatch

Character: Drew at Age 6

Masam Holden

Character: Drew at Age 10

Kelly Pendygraft

Character: Rebecca the Bridesmaid

Jennifer Woods

Character: Bridesmaid

Alana Ball

Character: Maid of Honor

Russell George

Character: Russ from Ernestine and Hazel's

Ralph Conlee

Character: Man on the Bench

Billy Tencza

Character: Brett

Hailey Knight

Character: Isis

Nicky Roos

Character: Sharon's Son

Zane Rice

Character: Little Chapel Boy

Kassie Pinegar

Character: Little Howling Girl

Daya Fernandez

Character: Mercury Shoe Designer

Michael Jaroscak

Character: The Young Recruit

Nigel Miguel

Character: Basketball Coach

Samantha Ray

Character: Frightened Memorial-goer

Nicole Spector

Character: Other Girl in Red Hat

Leslie David Baker

Character: Airport Security #2 (uncredited)

John D. Crawford

Character: Executive Shoe Designer

Joe Koons

Character: Cousin Jimmy (uncredited)