9. Go (1999)
Director: Doug Liman
Stars: Katie Holmes, Sarah Polley, Scott Wolf, Jay Mohr, Timothy Olyphant
"They can't evict you on Christmas! Then you'd be ho-ho-homeless!" So begins the impetus for this fast-paced black comedy-thriller, which takes place over 24 hours between Christmas Eve and Christmas Day.
Before she was Mrs. Tom Cruise or The Ex Mrs. Tom Cruise, Katie Holmes was Claire, a 20-something grocery store clerk behind held as collateral in exchange for 20 hits of ecstasy. The "dealer" who made the trade is Ronna (Sarah Polley), Claire's friend and co-worker who is desperate to make this month's rent. When the opportunity arises to sub for co-worker/dealer Simon (Desmond Askew), and provide minor celebs/police informants Adam (Scott Wolf) and Zack (Jay Mohr) with the drugs in question, Ronna finds a way to make a deal with tough-guy supplier Todd (Timothy Olyphant). Which is where Holmes comes in. Confused yet?
Everything—including the holiday—is really just a subplot in director Doug Liman's highly anticipated follow-up to the megahit Swingers, written by frequent Tim Burton collaborator John August, who seamlessly interweaves three separate stories surrounding one drug deal gone bad. Amidst all the backstabbing, philandering, double-dealing, gunfire, drug use, and one near-fatal car accident, all is forgiven—at least for the day—when December 25th rolls around. Merry Xmas!