A frustratingly not-terrible action thriller.
The men in "Tomcats" are surrounded by beautiful women, but they hate and fear them. That alone is enough to sink the film, since no reasonable person in the audience can understand why these guys are so weirdly twisted. But then the film humiliates the women, and we wince when it wants us to laugh. Here is a comedy positioned outside the normal range of human response.
The movie belongs to an old and tired movie tradition, in which guys are terrified that wedding bells may be breaking up that old gang of theirs (only last week we had "The Brothers," an African-American version of the theme, but gentler and nicer). There is always one guy who is already (unhappily) married, one who is threatened with marriage, one who claims he will never marry and then the hero, who wants to marry off the unmarriagable one, to win a bet. This plot is engraved on a plaque in the men's room of the Old Writers' Retirement Home.
The twist this time: The guys all agree to pay into a mutual fund. The last one still single collects all the money. The fund quickly grows to nearly $500,000, so their fund must have bought hot tech stocks. (In the sequel, those same stocks--oh, never mind.) The guy who vows never to marry is Kyle (Jake Busey). He likes to take his dates golfing and run over them with the cart. They bounce right up and keep smiling. The guy who wants to collect the money is Michael (Jerry O'Connell). He comes into a valuable piece of information: Kyle met one perfect woman, cruelly dumped her and has always wondered if he made a mistake. Michael tracks down the woman, who is Natalie (Shannon Elizabeth), and enlists her in his scheme. She'll seduce and marry Kyle and get her revenge--oh, and she wants half the money, too.
The complication, which is so obvious it nearly precedes the setup, is that Michael and Natalie fall for each other. This despite the fact that by going along with his plan, she reveals herself as a shameless vixen. The movie then runs through an assembly line of routine situations, including bad jokes about S/M and a proctologist who suspects his wife is a lesbian, before arriving at a sequence of astonishing bad taste.