Playboy executive Roderick Blank (Simon Baker) is about to settle down after a full-life of many women. His overbearing platonic friend Trixie (Mindy Cohn) clumsily opens a mysterious email sent to him which reveals a list of all the women he will ever sleep with moving forward--101 to be exact listed in chronological order. Thing is his fiancée isn't last on the list; 72 other lucky ladies follow her. So needless to say his engagement dissolves as he starts burning through his list of pre-ordained sexual conquests. In bizarre Matrix-like fashion Roderick is coached by a trio of relationship experts who advise him on which women he should pursue. All is kosher until the last name on the list is Gillian DeRaisx (Winona Ryder)--also known as Death Nell a local serial killer who targets promiscuous men. Uh-oh. Simon Baker (The Devil Wears Prada) carries this film's charm on his shoulders; he is irresistible in his body language and shows just how much of a man's man he can be. He does a fine job a unique type of rascal tapped in an offbeat love story. Ryder is a weird hybrid of Chicago’s Catherine Zeta Jones and Who Framed Roger Rabbit Jessica Rabbit: a femme fatale with a bowl brunette wig that belies her black widow-like mystique. But Ryder is underdeveloped and this is little more than a star sizzle piece for her. The female supporting roles are all strong women including Sophie Monk Leslie Bibb and Julie Bowen with complex viewpoints despite just being numbers on his list. Who's that cuddly magic man in the all-white room? Ratatouille himself Patton Oswalt as Fred one of Roderick’s advisor. He's hilarious in his physicality and gives ordinary line reads a pro comic's touch sparking smiles every time he's on screen. Writer/director Daniel Waters best known for writing one of Winona Ryder's breakout films Heathers is a colorful name from the past dusted off to helm Sex and Death 101 his second directorial effort. The film’s sense of humor is oddly pitched and uneven and the predictability is ancient. When Roderick stumbles in the dark for his girlfriend's room in a strange house he of course ends up sleeping with the 88-year-old grandmother. Part of the problem is there are too many thematic elements being thrown together: dark humor intrigue and broad physical comedy resulting in a big mess. Let’s just say Sex and Death 101 will probably end up on Lifetime at some point.