Everything in One Night at McCool's leads up to the climactic finale. It seems as if writer Stan Seidel envisioned his ending first and worked backwards from there. In any case, the end is an elaborate sequence blending in violence with the Village People. Oddly enough, it works in its own, bizarre way and makes perfect sense within the confines of the movie. One Night at McCool's is not meant to be anything else than a loony movie, and for the most part it is. Everything revolves around Jewel (Liv Tyler, Onegin, Dr. T and the Women), a lust-inspiring woman who will stop at nothing to get her dream home. Her scam is to meet men, go home with them, then have her boyfriend Utah (Andrew Silverstein aka Andrew "Dice" Clay, Foolish, Whatever It Takes) rob the unlucky chap. This changes when she meets Randy (Matt Dillon, Wild Things, There's Something About Mary). Randy owns a house, has a job, and looks like a potentially good prospect, so she sets her sights on him. During the subsequent robbery attempt, Jewel shoots and kills Utah.

The narrative unfolds from three perspectives. Randy is telling his side of the story to Mr. Burmeister (Michael Douglas, Traffic, Wonder Boys), a hitman with a gravity-defying pompadour. Randy hates Jewel, because she is the impetus that causes his life to fall apart. He loses his job, his house, and essentially everything else. Randy's cousin Carl (Paul Reiser, The Story of Us, Get Bruce) is telling his side of the story to his psychiatrist. Carl is a married lawyer lusting after Jewel. For anybody who ever wanted to see Reiser in bondage gear, One Night at McCool's provides ample opportunity. The final narrator is Detective Dehling (John Goodman, The Emperor's New Groove, Coyote Ugly), telling all to a priest. Jewel reminds Dehling of his wife, so he feels an instant hatred towards Randy. He both lusts and cares for Jewel at the same time. As Jewel discovers that Randy may not be the perfect man, she begins to play Randy, Carl, and Dehling against each other.

Since there are three stories, the same scene sometimes plays more than once. Director Harald Zwart shows the same scene from different perspectives, each skewed towards the particular narrator's vision of Jewel. Goodman's scenes are amusing because of his attitude towards Randy, who Tyler does little more than pout and lean over wearing loose, low cut shirts. It's also hard to determine whether or not each additional travail for Randy is funny or exasperating. He continues to be Job-like because of the trade-off between sex with Jewel and a worry-free life, with the former winning for a very long time. The movie is sporadically funny, with many instances of Seidel and Zwart trying to stretch too far. There is only just so much time one can spend ogling Tyler.