![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](https://m.media-amazon.com/images/M/MV5BMTg5NTA0NjMwOF5BMl5BanBnXkFtZTYwOTgxMTk2._V1_.jpg)
![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)
Tomcats (2001)5 of 44
Shannon Elizabeth plays Natalie, Michael's secret weapon in his plan to bring the ultimate Tomcat down
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Photo by Joseph Viles - © Copyright 2001 - Columbia Pictures Inc. - All Rights Reserved