The film opens with seven friends dining at a Las Vegas casino, where they make a pact called the “Tomcats” agreement. Each of them contributes money to a collective pot, and the last remaining bachelor will win the entire sum. Among the friends are Michael Delaney (played by Jerry O’Connell) and Kyle Brenner (played by Jake Busey), who emerge as the main characters.
Years later, Michael finds himself in dire financial straits and desperate to win back the money from the Tomcats agreement. He learns that his childhood friend, Kyle, is the last remaining bachelor and has accumulated a substantial amount of money. Michael concocts a plan to seduce and marry Natalie Parker (played by Shannon Elizabeth), Kyle’s wealthy ex-girlfriend, so he can divorce her and collect a share of the pot.
As Michael executes his plan, he discovers that Kyle is now engaged to marry Natalie, jeopardizing his scheme. Determined to win back the money, Michael enlists the help of his friends to sabotage Kyle’s wedding and ensure that he remains single.
However, things take an unexpected turn when Michael develops genuine feelings for Natalie and begins to question his motives. Meanwhile, Kyle becomes suspicious of Michael’s intentions and attempts to uncover the truth about his friend’s ulterior motives.
In a series of comedic and outrageous mishaps, Michael and his friends engage in various schemes to thwart Kyle’s wedding and win back the money from the Tomcats agreement. Along the way, they encounter a cast of eccentric characters, including a private investigator hired by Kyle to spy on Michael and Natalie.
In the end, Michael realizes the error of his ways and confesses his love for Natalie, putting an end to their devious schemes. Kyle forgives Michael for his betrayal, and the two friends reconcile their differences. The film concludes with Michael and Natalie getting married, and the friends celebrating their newfound happiness and camaraderie.
“Tomcats” is a raunchy and irreverent comedy that blends slapstick humor with heartfelt moments of friendship and romance. Through its outrageous premise and zany characters, the film delivers laughs and entertainment while also exploring themes of loyalty, love, and the complexities of male friendship.