Jake Busey and Jerry O'Connell in Tomcats (2001)

Natalie (Shannon Elizabeth) is Michael's (Jerry O'Connell) partner in crime in his scheme to win the bachelor pool

Michael Delaney (Jerry O'Connell, center) celebrates at a bachelor party for Kyle (Jake Busey), the buddy he is marrying off in order to win a bet that will pay off his Vegas casino creditors

Shannon Elizabeth plays Natalie, Michael's secret weapon in his plan to bring the ultimate Tomcat down

Jerry O'Connell stars as Michael Delaney, a cartoonist who cooks up an outrageous scheme to win a bachelor betting pool 

When Kyle (Jake Busey) and Natalie (Shannon Elizabeth) get closer, Michael has to decide how important collecting the jackpot really is

Jake Busey plays Kyle, a notorious womanizer

Willing to do anything for his fellow Tomcat, Michael (Jerry O'Connell) furiously chases after Kyle's runaway body part

Meet the Tomcats, a group of freewheeling, sex-fueled single buddies who go up against each other in a betting pool that will leave the "last man standing" unmarried with the jackpot

Even though a sexy Vegas redhead (Amber Smith) rubs Michael's (Jerry O'Connell) dice for good luck, he still drums up a $51,000 casino debt

Life in Michael's (Jerry O'Connell) apartment gets increasingly bizarre as his furniture, clothing and other belongings decrease at the hands of the casino boss's repossessors

Michael Delaney (Jerry O'Connell) finds himself in a bind after going home with a gorgeous librarian

Jake Busey, Shannon Elizabeth, Jerry O'Connell, Jaime Pressly, and Horatio Sanz in Tomcats (2001)

Jaime Pressly, Sole Alberti, and Kinga Philipps in Tomcats (2001)

Jake Busey and Shannon Elizabeth in Tomcats (2001)

Shannon Elizabeth and Jerry O'Connell in Tomcats (2001)

Jake Busey, Shannon Elizabeth, and Jerry O'Connell in Tomcats (2001)