Tomcats (2001)

From the opening animated title sequence to the vulgarities at the film's climax, Gregory Poirer's directing debut is an obnoxiously funny comedy with a sharp romantic edge flowering beneath its T&A exterior. The plot surrounds a "kitty" (double entendre intended), created by a group of swinging pals determined to stave off marriage at all costs, with the cash headed towards whoever stays single the longest. Seven years later, only two of the friends remain single, and the pot is up to a half million in cash. When one of the two singles, Michael Delaney (Jerry O'Connell), runs afoul of the Las Vegas gambling mafia on account of a big-breasted babe, he needs that kitty cash desperately. Michael attempts to con his competitor, Kyle Brenner (Jake Busey), into marrying the wildly attractive policewoman Natalie (Shannon Elizabeth), who holds a personal vendetta against Kyle. But the best laid plans begin to run afoul when Natalie and Michael fall for each other instead. Filled with totally gross sex gags, pot shots at other films, and slapstick humor, TOMCATS is a humorous take on adult men who have not outgrown their adolescent mentalities about love, sex, and relationships.