Tomcats

Tomcats (2001) is an American comedy you can watch online on iFILM, directed by Gregory Poirier. Back in college, a group of friends pooled money into a winner-takes-all pot: the last one to stay single walks away with the cash. Seven years later, the kitty has grown to half a million dollars and only two guys are left.

Jerry O'Connell plays Michael, who desperately needs that money to clear a gambling debt before it turns dangerous. His plan: find a way to get the other holdout — Jake Busey's incorrigible womanizer — to walk down the aisle. Shannon Elizabeth gets pulled into the scheme. The humor is blunt and deliberately immature, squarely in the tradition of early-2000s raunch comedies. It knows its lane and stays in it. Stream Tomcats (2001) online on iFILM.