Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.
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
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)
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