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
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
