Seven years earlier after a friend's wedding a group of guy pals vow to stay single for life. To sweeten the deal they put some money into a stock portfolio with the last remaining bachelor taking home the accumulated jackpot which has since grown to a whopping half a million dollars (the 90s market remember?) The competition comes down to two remaining tomcats Michael (Jerry O'Connell) and Kyle (Jake Busey) but the stakes are raised when Michael a struggling cartoonist becomes indebted to a casino owner for $51 000. Facing a certain and painful death if he fails to repay the debt within 30 days Michael plots to get Kyle to the alter with Natalie (Shannon Elizabeth) a former one-night stand who will do the deed for half of the prize money. Problem is Kyle is a sexist jerk and the future bride is a smart and beautiful cop who has her eyes on Michael. While this film doesn't have too many redeeming qualities Jerry O'Connell is one of them. His character Michael Delaney is one of the few characters in the movie with a conscience. Working from a script that consists mostly of one boner joke after another O'Connell fares quite well considering the lines he has to deliver. He even becomes the underdog you end up rooting for. Jake Busey is a different story altogether: his character Kyle does not evoke the slightest shred of sympathy even as he lies on a hospital bed battling testicular cancer. Kyle is crass vulgar and chauvinistic. He treats women like dirt spewing lines like "I don't want a feminist bitch who'll keep her own name when you marry her." Natalie Parker who plays O'Connell's love interest gives a fair but slightly lackluster performance as an unrealistically bright sharp-shooting cop with a bone to pick. In one scene she casually discusses her love life with her partner during a shoot out in a crack house. Bill Maher (best known for hosting the late-night talk show "Politically Incorrect") makes a cameo appearance as the casino owner. The rest of the cast consists of a lot of blondes who all resemble one another. Gregory Poirier (See Spot Run) who wrote and directed Tomcats knows his audience and gets right to the point. The film does not try to be clever and it may actually alienate anyone who is not a hormone-laden frat boy. The story is lame and predictable and most of the characters are obnoxious and detestable. There is no outstanding cinematography to speak of and there are no special effects. But let's face it Tomcats' target audience is not going for great visuals. They want their jokes Porky's style and Tomcats definitely delivers those. In a film that features librarian-by-day-dominatrix-by-night story lines lesbian fantasies and Viagra jokes Poirier is too busy catering to teenage boys to worry about being offensive to everyone else.