After causing the Oregon shoe company he works for to lose hundreds of millions of dollars, Drew Baylor is fired for his mistake, and promptly also dumped by his girlfriend, Ellen. On the verge of suicide, Drew is oddly given a new purpose in life when he is brought back to his family’s small Kentucky hometown of Elizabethtown following the death of his father, Mitch, as it falls to him to make sure that his dying wishes are fulfilled. On the way home, Drew meets a flight attendant, Claire Colburn, with whom he falls in love, in a romance that helps his life get back on track.
- Orlando Bloom as Drew Baylor
- Kirsten Dunst as Claire Colburn
- Susan Sarandon as Hollie Baylor
- Alec Baldwin as Phil Devoss
- Jessica Biel as Ellen Kishmore
Jessica and then-boyfriend Chris Evans both auditioned for the respective lead role, Jesse was cast as Ellen instead.
- Grammy Awards – Best Song Written for Motion Picture, Television or Other Visual Media, Tom Petty (Nominated)
- Hollywood Film Awards – Supporting Actress of the Year, Susan Sarandon (Won)