Orlando Bloom as Drew Baylor

Kirsten Dunst as Claire Colburn

Susan Sarandon as Hollie Baylor

Alec Baldwin as Phil DeVoss

Bruce McGill as Bill Banyon

Judy Greer as Heather Baylor

Jessica Biel as Ellen Kishmore

Paul Schneider as Jessie Baylor

Loudon Wainwright III as Uncle Dale

Gailard Sartain as Charles Dean

Jed Rees as Chuck Hasboro

Paula Deen as Aunt Dora

Dan Biggers as Uncle Roy

Alice Marie Crowe as Aunt Lena

Tim Devitt as Mitch Baylor

Ted Manson as Sad Joe

Maxwell Moss Steen as Samson

Reid Thompson Steen as Samson

Shane Lyons as Starstruck Kid

Emily Rutherfurd as Cindy Hasboro

Michael Naughton as Another Cousin

Griffin Grabow as Griffin

Nina Jefferies as Staring Mona

Emily Goldwyn as Star Basketball Player

Kristin Lindquist as Connie

Allison Munn as Desk Clerk Charlotte

Tom Humbarger as Crematory Concierge

Patty Griffin as Sharon

Gregory North as Helicopter Pilot

Steve Seagren as Dock Worker

Guy Stevenson as Security Guard

Jeffrey De Serrano as Security Guard

Jeanette O'Connor as Assistant

Catherine McGoohan as Assistant

Sean Nepita as Mike Bohannon

Dena DeCola as Debbie

David Brandt as Hotel Manager

Jenny Gregg Stewart as Loud Kid

Delaney Keefe as Loud Kid

Travis Howard as Electrician

Bobby Daniels as Des

Rod Burke as Raymond

Nate Mooney as Trent

Judy Pryor Trice as Woman in Finery

Jim Fitzpatrick as Rusty

Jim James as Jessie's Band

Two-Tone Tommy as Jessie's Band

Patrick Hallahan as Jessie's Band

Charlie Crowe as Jessie's Band

Carl Broemel as Jessie's Band

Scott Sener as Jessie's Band

John M. Sullivan as Etown Veteran

Sonny King as Etown Veteran

Erwin Russell Marlowe as Etown Veteran

Michael Hatch as Drew at Age 6

Masam Holden as Drew at Age 10

Kelly Pendygraft as Rebecca the Bridesmaid

Jennifer Woods as Bridesmaid

Alana Ball as Maid of Honor

Russell George as Russ from Ernestine and Hazel's

Ralph Conlee as Man on the Bench

Billy Tencza as Brett

Hailey Knight as Isis

Nicky Roos as Sharon's Son

Zane Rice as Little Chapel Boy

Kassie Pinegar as Little Howling Girl

Daya Fernandez as Mercury Shoe Designer

Michael Jaroscak as The Young Recruit

Nigel Miguel as Basketball Coach

Samantha Ray as Frightened Memorial-goer

Nicole Spector as Other Girl in Red Hat

Leslie David Baker as Airport Security #2 (uncredited)

John D. Crawford as Executive Shoe Designer