A variety of crooks, losers, and working stiffs living in the shadow of Hollywood find their various personal crises overlapping in this intricately woven melodrama. Lee Woods (James Spader) is a cold-blooded hit man and Dosmo Pizzo (Danny Aiello) a soft-at-heart gangster; they've been sent to murder Roy Foxx (Peter Horton), the former husband of also-ran Olympic skier Becky Foxx (Teri Hatcher). Lee's girlfriend Helga (Charlize Theron) is unhappy about his habit of killing people, and she attracts the attention of Alvin (Jeff Daniels) and Wes (Eric Stoltz), two cops who've been put on vice detail but don't have the heart to bust the prostitute they've been trailing. Alvin dreams of becoming a homicide detective, so when he discovers that he might be on the trail of a murder, it's like Santa Claus showed up in mid-July to hand him a present. Dosmo manages to escape the crime scene, only to foil a murder attempt by Lee, forcing him to hide out in the home of Hopper, a pretentious English art dealer (Greg Cruttwell), whom Dosmo holds hostage along with Hopper's long-suffering assistant, Susan (Glenne Headly).
This romantic melodrama reunites The Devil's Advocate (1997) co-stars Keanu Reeves and Charlize Theron, and is directed by Irish filmmaker Pat O'Connor (Circle of Friends). Sara Deever (Theron) is a beautiful young woman who begins a new romantic relationship with a man each month, then helps him to evolve into a better and kinder human being before she moves on to the next partner. Although she's remained friendly with some of her former lovers, she's never broken her one-month rule. November's candidate is a particularly heartless business exec named Nelson Moss (Reeves), who takes a while to come around. Once he does, however, Nelson falls deeply in love, hoping to woo Sara for good; eventually, her resolve weakens. What Nelson doesn't know is the tragic secret behind the brevity of Sara's romances.
After being imprisoned for six years on a grand theft auto charge, Rudy Duncan (Ben Affleck) and his cellmate Nick (James Frain) are finally going to be paroled. After hearing endless stories during his incarceration of Nick's romantic correspondence to a woman named Ashley he has never met (Charlize Theron), Rudy is looking forward to returning to his family and having a fresh cup of hot chocolate.