Tomcats (2001)

Jerry O'Connell is a struggling cartoonist who really needs some moolah, and he just might get it if he can get his pal hitched in Tomcats (2001). Years ago, Michael Delaney (Jerry O'Connell) and seven buddies made a pact that whoever was the last to marry would get a big honking cash reward they all set aside. Now, the fund has exploded thanks to a few of its investments hitting it big, and out of the initial eight dudes only Michael and Kyle Brenner (Jake Busey) are still bachelors. Michael is deep in debt to a Vegas casino boss, so he could really use that money, but because Jake is a total pig, the chances of him getting hitched are essentially nil. With no other option, Jerry decides to give it the old college try. His only hope is to track down an old love of Kyle's named Natalie (Shannon Elizabeth). But when Michael and Natalie start to fall in love, our cartoonist has to decide between love or money. Put a ring on it and your thing in it, or take the money and run? When it comes to Shannon Elizabeth, Mr. Skin says make her your ball and chain and go balls deep in her! Shannon's legendary large lactation devices don't make an appearance in this one, since all we get is a weird dream sequence scene where she opens her legs to pop out a baby. We prefer to see the baby making process. Jerry makes out with Julia Schultz while she's in a white bra and panties, but when she wants him to say he loves her, he won't, so she storms off without getting him off. We did not love that skin tease! Amber Smith is a busty redhead wearing a very cleavage heavy dress in a casino, while Heather Stephens is another scorching hot redhead you'll want to take to bed! She plays a librarian that's secretly a freaky dominatrix. After checking her out, she might not be as busty, but definitely had us feeling super lusty thanks to her strapping Jerry down and whipping him in black lingerie. The only real skin we get comes when Rachel Sterling slips nip a few times as a wild stripper hanging out with the boys, but that's mostly accidental. Cash can't compete with amazing cans! After seeing Tomcats, every Tom, Dick and Harry would be happy to marry a girl like Shannon Elizabeth!