The idea for TOMCATs came to writer/director Gregory Poirier when he overheard a couple of college buddies discussing their own bachelor bet.
When Poirier had completed this next draft, the search began for two actors to play the lead characters, Michael Delany and Natalie Parker. The trio met early on with Jerry O'Connell. He was drawn to appearing in an outlandish comedy.
The filmmakers cast several featured extra roles by working closely with Mediatrip.com. Users of the site were invited to submit their photos to the site for consideration by Tomcat's casting director. Four actress-hopefuls were selected to appear in the film - from Delaware, Texas, Massachusetts and Ohio.
The scene with Michael and the dominatrix pays a homage to the classic story of "Little Red Riding Hood" For Example: Jill The dominatrix lives in a house with her grandma in a house with a picket fence. In the story of "Little Red Riding Hood", the big bad wolf locks up or eats the real grandma, then disguises himself as the grandmother to lure Little Red Riding Hood into his trap. Tomcats does it in the opposite, The dominatrix disguises herself as a shy librarian to lure men into her trap. Also at the end of the movie Michael's friend Kyle comments Jill about her being a 'Big bad dominatrix'.
The filmmakers cast as support to the two leads, Jake Busey, Horatio Sanz and Jamie Pressly plus Playboy stars Julia Schultz and Amber Smith. Schultz had been Miss February 1998 and Smith-March 1995.
After getting Jerry O'Connell and Shannon Elizabeth as the leads, Paul Kurta was brought in as Line Producer. He then produced a budget.
Jerry O'Connell gets crucified by Jill the dominatrix in this film very similarly to the way he is crucified by the killer near the end of Scream 2 (1997).
Michael's dream sequence in which Natalie is surrounded by rose pedals is a spoof of the dream sequence in the 1999 film American Beauty. Amber Smith who played the redhead woman who tricks Michael into gambling at the casino was also in American Beauty.
Michael seduces a seeming shy librarian who turns out to be a dominatrix named Jill. Which is ironic, Shannon Elizabeth who plays Natalie Parker also appeared in the 1997 direct to video horror film Jack Frost as one of Jack Frost's victims named Jill.
Gregory Poirier completed the first draft. He then got a couple producers he knew, Alan Riche and Tony Ludwig, and asked them to join him in writing another draft of the script.
After getting a producer, a script, two stars and a shooting plan, Gregory Poirior took the film to the newly formed Revolution Studios. The founder, Joe Roth (formerly of 20th Century Fox), could not overlook this ready-made opportunity for the newly-formed company's first project.
Revolution Studios founder Joe Roth, called the producers and asked them how much the project would cost. '$11 million' was the answer.