Tomcats (2001)

There is only one person standing in his way… Kyle (Jake Busey), a notorious womanizer and Michael’s competition to win the bet, the money and his life back. It seems hopeless, but Michael has a secret weapon… Natalie (Shannon Elizabeth).

Meet the Tomcats, a group of freewheeling, sex-fueled single buddies as they go up against each other in a betting pool that will leave the "last man standing" unmarried with the jackpot. The first victim, Steve (Horatio Sanz), succumbs to holy matrimony with the luscious Tricia (Jaime Pressly) in Las Vegas. Fast-forward seven years to today, when all of the Tomcats are now married and starting families with the exception of two confirmed bachelors…

First, Michael, a talented yet struggling cartoonist who hides the soul of a nice guy somewhere below his philandering exterior. During a night of Las Vegas debauchery (where he gets himself in trouble with yet another buxom and brazen redhead), he drums up a $51,000 casino tab (plus the mini-bar) that he can’t pay. Michael is faced with a deadly ultimatum to either cough up the dough in a month or suffer a painful death at

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