Drew Baylor
Orlando Bloom
A shoe-designer, one of whose creations goes fiasco and he gets fired.
During a hometown memorial for his Kentucky-born father, a young man begins an unexpected romance with a too-good-to-be-true stewardess.
During a hometown memorial for his Kentucky-born father, a young man begins an unexpected romance with a too-good-to-be-true stewardess.
Orlando Bloom
A shoe-designer, one of whose creations goes fiasco and he gets fired.
Kirsten Dunst
A flight attendant that helps Drew through is life.
Susan Sarandon
Drew's mother.
Alec Baldwin
Owner of the shoe-company Drew worked for.
Drew's ex-girlfriend.
Drew's sister.
Drew's cousin.
Gailard Sartain
The funeral director.
Loudon Wainwright III
Drew's uncle.
Tim Devitt
Drew's deceased father.
Bruce McGill
An old friend of Mitch Baylor.
Maxwell Moss Steen
Jessie's son.
Desk clerk at the Hotel that Drew checks in to.
Half of Chuck & Cindy, who are having a massive marriage party in Drew's hotel.