Sex and Death 101 (2007)

"Sex and Death 101" is a dark and savvy little romantic comedy that gleefully dances away from many of the stale and stuffy conventions generally associated with the genre.

Simon Baker stars as the allegorically named Roderick Blank, a handsome, seemingly insatiable lady killer who's decided it's finally time to put an end to his womanizing ways in favor of marriage to the beautiful Fiona Wormwood. Yet, literally on the eve of his bachelor party, Rod receives a mysterious email listing in chronological order not only all the women he's already slept with throughout the course of his life but all the women he is destined to sleep with in the time that still remains to him (the total is 101, if you haven't already surmised that from the film's title). Adhering to the adage "the spirit is willing but the flesh is weak," Rod allows the list to essentially take over his life, waiting for the next promised woman to fall into his lap (sometimes quite literally), then crossing her name off the moment he's had his way with her. But is this truly the route to a satisfying life, even for a notorious playboy like Roderick Blank?

Part science fiction and part metaphysical morality play, "Sex and Death 101" also boasts two wacky subplots that run contrapuntal to the main story: one featuring Winona Ryder as an avenging feminist who comes in the guise of a serial killer, luring unsuspecting misogynists to their well-deserved destruction; and the other involving three mysterious figures (mad scientists, intervening angels?) who kidnap Rod to inform him that he has been the victim of some bizarre cosmic prank and that he needs to destroy the list before it destroys him.

"Sex and Death 101" is not a perfect film by any means. Its attempts at surrealism are frequently heavy-handed and strained, and its black-comedy edge isn't always as razor-sharp as it could be. But, on the whole, this is a wildly original and surprisingly incisive look at the different ways in which men and women view sex and romance and the different ways they use both those things to get what they want. Writer/director Daniel Waters knows how to set even the most hackneyed romantic comedy cliché spinning on its head. For instance, the movie takes the obligatory "gay best friend" stereotype - who usually comes in the form of a flaming interior decorator or wedding planner - and turns it into a wise-cracking lesbian (smartly played by Mindy Cohn, best known as Natalie from "The Facts of Life"), whose duties as Rod's personal secretary go far beyond merely scheduling his appointments or knowing where his briefcase is.

Although Rod is, in many ways, a typical character for a romantic comedy - afraid of commitment, obsessed with nailing every woman who comes his way, etc. - the route the script takes to get him to his admittedly rather predictable pro-woman/pro-romance epiphany is anything but typical. This freshness is further enhanced by the devilishly playful and utterly disarming performance turned in by Baker who completely captivates the viewer with his easygoing charisma and charm. The scene in which Baker and Ryder finally share screen time together is exceptionally well acted and staged.

Even though the movie feels a little disjointed and unfocused at times, Waters does a nice job dovetailing all the seemingly unrelated plot elements into a satisfying whole in the end. "Sex and Death 101" is for those who like a little spice with their romantic comedies.