Summary
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.
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Cast
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)