A group of guys Michael Delaney, Kyle Brenner, Steve and other characters, are talking before the wedding ceremony of one of their friends. They agree to a pact whereby they will all invest in a fund that only the last bachelor will inherit. Michael attends Vegas years later with Steve and his girlfriend. After going back to their room she asks him to utter "those 3 words" which he mistakes for "I love you". He panics and kicks her out of the room and she dumps him. He goes on a bender and picks up a sultry redhead who encourages him to gamble at the roulette table. He goes on an amazing run of bad luck losing everything and taking out credit from the casino. In the end the casino intervenes and he is summoned to meet the pit boss Carlos. Carlos informs Michael how serious the trouble he is in and what will happen if he fails to repay the debt. Michael realises that Kyle and him are now the last men standing and stand to inherit the entire fund which has swelled to an enormous fund. He approaches Kyle and learns that Kyle is wealthy and a jerk. He decides, his only option is to set Kyle up so that Michael can inherit the fund. He learns on a drunken night that Kyle has only ever loved one woman, a lady called Natalie he met at Steve and Tricia's wedding. Michael approaches Steve and Tricia and finds out where Natalie is. Unfortunately they neglect to tell him that Natalie is a police detective. Natalie is working undercover as a street walker when Michael finds her and he inadvertently gets himself arrested for solicitation. During interrogation he admits everything and is eventually released. Natalie visits him and agrees to go in with his plan on the basis that she gets half the money. He finds out that Kyle's memory of Natalie and his night together left out some important details. Notably, that when Natalie woke up Kyle had bolted and left her with a bag of quarters to get a cab home. Michael and Natalie decide to spend time together investigating Kyle in order to ensure their plan works. It all appears to be working until Michael realises he is falling in love with Natalie. Natalie too is falling for Michael but decides to go ahead with marrying Kyle. During the bachelor party Kyle informs Michael he has no intention of quitting womanising and believes Natalie to be the perfect stay at home wife. Before Michael can act and prevent the wedding he is knocked unconscious by a bowling ball. He wakes up finds his clothes are missing. He grabs some clothing from an unconscious stripper and tries to run to the civic hall to prevent the marriage. After a number of misadventures Michael finally arrives but learns that he is too late and Kyle has already married Natalie. He leaves somewhat dejectedly. Michael goes on to claim the fund and thereby settles his debt with Carlos. He later bumps into Kyle who is on a date with another woman and punches him as he believes Kyle to be cheating on Natalie. Kyle beats up Michael and then discloses that he has split with Natalie. On their wedding night she knocked him out cold and when he woke up he found a bag of quarters. Michael runs off to find Natalie and finds her again working undercover. He proposes that they date and he give up his tomcat ways. A side story running in parallel to the main story involves Michael's best friend Steve and his wife Tricia. Steve suspects Tricia to be a lesbian who is cheating on him with their maid, their trainer and a mailwoman. In the final scene he uncovers the truth and Tricia invites him for a threesome.
Cast
, Shannon Elizabeth's husband at the time, has a cameo as a man trying to pick up Elizabeth's character at the end of the film. Bill Maher has an uncredited role as Carlos, the casino owner whom Michael owes money to. Tomcats also marked Bernie Casey's final appearance in a theatrically released film. This was also actress Dakota Fanning's first movie appearance.
Reception
The film has a 14% approval rating on Rotten Tomatoes from 76 critics. The summary statement is: "Why even bother? You already know if you're going to see it or not." Peter Travers of Rolling Stone said "Tomcats is laced with such rampant misogyny that the laughs stick in your throat." The New York Times said, "The film is enthusiastically vulgar but not particularly funny, perhaps because it too often loses the distinction between gross-out humor and the merely gross."
