Randy (Dillon), a down-on-his-luck bartender at the epononymous McCool's has his life turned upside down when he encounters seductress Jewel Valentine (Tyler), whom he saves from what initially seems to be her abusive boyfriend Utah. After a turn of events ends up with Utah murdered, the two become a couple. However, not long afterwards, two more men; Randy's cousin Carl (Resier) who is a sadomasochistic lawyer, and police detective Dehling (Goodman) who is investigating Utah's murder and grieving the death of his late wife; also develop obsessions with Jewel. The three men develop wildly different opinions of who Jewel is and what she is like, and the film primarily consists of the three recounting their personal interpretations of various events pertaining to her.
This film provides examples of:
- Attempted Rape: Greg had attempted this on Jewel, but was unable to do so as Jewel had fought back against him, leading to him getting accidentally killed.
- Black Comedy: Only Randy, Jewel, and the hitman survive the climax.
- Cut Himself Shaving: Jewel received a black eye in an accident. A police officer later sees her at her boyfriend's house; he immediately assumes that the boyfriend had beat her and kicks him out of his own house. The boyfriend keeps imploring her to tell the officer the truth, but she says absolutely nothing the entire time because she's a Manipulative Bitch.
- Dropped a Bridge on Him: The film ends with a dumpster just randomly falling on top of Carl and crushing him after he just barely escaped a shootout with his life. Done for absolutely no reason besides Rule of Funny.
- Gaussian Girl: Jewel, the havoc wreaking femme fatale, is shown this way when each of the three guys see her for the first time. She's played by Liv Tyler, who just has one of those faces.
- Groin Attack: Halfway through the movie, Jewel accompanies a man named Greg back to his own home. When Greg attempts to have his way with her, Jewel refuses to do so, leading to her getting slapped by Greg from upon his bed and as Greg tells Jewel that he's gonna enjoy himself upon her (a.k.a. Attempted Rape), Jewel gets pissed and proceeds to kick him in the groin with her right leg before throwing a right uppercut punch against him and then using both of her feet to knock him back away from her.
- Karma Houdini: While Jewel doesn't get the perfect home that she wanted, she doesn't get any comeuppance for her crimes either, and is free to continue being The Vamp with the hitman she hooks up with at the end.
- Not What It Looks Like: Late in the film, Jewel arranges a "date" with both Carl and Dehling at the same time without their knowledge. At Jewel's request Carl gets into a submissive S&M outfit, while Dehling goes to meet her in his police uniform. When Dehling later finds Carl in the house he restrains the apparent stranger on the kitchen table. At this point Carl's cousin Randy walks in and asks them what the heck is going on.
- "Rashomon"-Style: Three different male characters relate their often conflicting impressions of Liv Tyler's character Jewel, revealing the particular brand of misogyny present in each one.
- Shout-Out: To the other Michael Douglas' role in Falling Down.
- Soundtrack Dissonance: Done with the Village People's song "YMCA" being played to a crazy shootout scene
- Spit Take: Randy does one of these after he's just offered the sultry Jewel some water, and she reveals that her favorite thing in the world is sex.
- Take a Moment to Catch Your Death: At the end, Carl's character escapes a shootout between Dehling and Utah's twin brother, and runs across a street screaming an elated "Thank you God!" only to have a dumpster dropped on his head.
- The Vamp: Jewel