Revolution Studios’ partner, Todd Garner, an executive producer, is no stranger to comedy with a number of box office hits to his credit. Garner felt the material fit perfectly with the types of films Revolution Studios wanted to make. He comments, "It’s a nice way to get our studio off the ground. We wanted to get out there with a comedy that we knew had the potential to cross over and be a big commercial hit. You’re going to see some things you’ve never seen before."
Filming began soon after with Jerry O’Connell hitting the ground running—literally. He spent the first two days running throughout the corridors and stairwells of a medical center in the San Fernando Valley chasing a rogue, bouncing ball (Kyle’s wayward testicle) in one of the film’s more hilarious action sequences.
To O’Connell’s chagrin, the filmmakers broadened his character even further. Scripting Michael as a cartoonist provided the perfect starting point for much of the character’s outrageous slapstick comedy. No matter what happens, he’s always surviving, like a cartoon character bouncing back and coming back for more.
O’Connell had to serve up some romantic moments as well. Alan Riche points out that the actor handled them with equal aplomb. "Jerry is utterly likable on screen. You feel very drawn to him because he is very romantic in a very accessible way." Elizabeth echoes Riche’s sentiment, citing those romantic scenes with O’Connell as her favorites. Remarks Elizabeth, "I think Jerry’s amazing… those scenes were a lot of fun to shoot. You really feel it when you’re there and in the moment and everything is working."
The role of Natalie Parker offered Elizabeth a chance to work with a character that was more multi-dimensional than those she has previously played in the horror spoof Scary Movie and American Pie. Remarks Elizabeth, "There are a lot of different shades to her…it’s an exciting role. I’m getting a lot more serious moments out of this film than I’ve gotten in the past."
Joining O’Connell and Elizabeth in this unlikely love triangle is Jake Busey as the boorish Kyle Brenner. Busey was actually one of the first actors to meet with the filmmakers for the role of Kyle and the one they kept returning to when discussing the dynamics of the character. Busey, who had been cast in the role of the heavy in several dramatic films, was excited about the prospect of doing a comedy. "It’s one of those projects where you’re on the phone with your manager saying, ‘What’s going on with Tomcats? I’ve got to do this film!’ It’s the funniest script I’ve read in a while… and I loved the character of Kyle. I knew he was going to be really fun to play."
Although Kyle could be pegged as the villain in the film, Busey is forgiving of the character’s less than gentlemanly qualities. Remarks Busey, "Kyle is just the kind of guy who gets what he wants because he thinks he can. He is one of those guys that’s very full of himself and maybe a little bit of a womanizer."
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