![Shannon Elizabeth plays Natalie, Michael's secret weapon in his plan to bring the ultimate Tomcat down](https://m.media-amazon.com/images/M/MV5BMTQzNDQxMTMwMF5BMl5BanBnXkFtZTYwNDkxMTk2._V1_.jpg)
![Jerry O'Connell stars as Michael Delaney, a cartoonist who cooks up an outrageous scheme to win a bachelor betting pool](https://m.media-amazon.com/images/M/MV5BMTIwNTAzMDY2N15BMl5BanBnXkFtZTYwNjkxMTk2._V1_.jpg)
![When Kyle (Jake Busey) and Natalie (Shannon Elizabeth) get closer, Michael has to decide how important collecting the jackpot really is](https://m.media-amazon.com/images/M/MV5BMjA2OTg5Njc0MF5BMl5BanBnXkFtZTYwNzkxMTk2._V1_.jpg)
Tomcats (2001)6 of 44
Jerry O'Connell stars as Michael Delaney, a cartoonist who cooks up an outrageous scheme to win a bachelor betting pool
PeopleJerry O'Connell
TitlesTomcats
Photo by Joseph Viles - © Copyright 2001 - Columbia Pictures Inc. - All Rights Reserved