Elizabethtown (2005)

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.

Director:

Cameron Crowe

Stars:

Orlando Bloom (Drew Baylor), Kirsten Dunst (Claire Colburn), Susan Sarandon (Hollie Baylor), Alec Baldwin (Phil DeVoss), Bruce McGill (Bill Banyon), Judy Greer (Heather Baylor)