It centers on Paul Benjamin (Hurt), a writer still mourning the loss of his wife, Rashid (Perrineau), a street kid who saves Paul's life one day, Auggie Wren (Keitel), owner of the cigar store Paul frequents, Ruby (Channing), Auggie's ex-girlfriend, and Cyrus (Whitaker), Rashid's biological father.
Followed later that year by a spin-off movie, Blue in the Face.
This movie contains examples of:
- Adaptation Expansion: The movie is based on the short story "Auggie Wren's Christmas Story" by Paul Auster. The entire story is filmed in the last 12 minutes of the movie (as well as part of what plays over the closing credits); everything that happens before then was made up by Auster and co-writer/director Wayne Wang.
- Author Avatar: Paul Benjamin.
- Chekhov's Gun: The bag of money Rashid took from the Creeper.
- Deadpan Snarker: Paul and Rashid.
- Everybody Smokes: All the main characters in this movie smoke, and Paul and Auggie are seen smoking throughout. However, near the end, Paul buys only one box of cigarettes rather than two because he's trying to cut down.
- Mama's Baby, Papa's Maybe: This is how Ruby gets Auggie to help her confront Felicity, by claiming she's his daughter. Afterwards, Ruby admits she doesn't know for sure.
- The Matchmaker: Rashid asks a bookstore clerk out for Paul.
- Nice Job Breaking It, Hero!: Auggie to Rashid after Rashid accidentally spills water on the Monte Cristo cigars Auggie was planning on selling, and thereby ruining them.
- Self-Plagiarism: The story Paul tells Rashid about the boy who discovered his father frozen in a block of ice is taken from Auster's novel The New York Trilogy.
- Shout-Out: "So he huffed and he puffed, and he smoked his book."
- Tempting Fate: Auggie is sure nothing will go wrong with the Monte Cristo cigars he plans to sell.
- Waxing Lyrical: When Auggie hears Rashid has just turned 17, he starts trying to sing "It was a Very Good Year" before giving up.
- White Man's Burden: Paul helping Rashid to reconcile with his father.