Unlucky Bernie Lootz (Macy) has little going for him: He lives in a dreary studio apartment in a rundown motel on the Las Vegas Strip, he's indebted to Shangri-La casino boss Shelly Kaplow (Baldwin), who years earlier cured him of a gambling habit by destroying his kneecap, and he can't recall the last time he had physical contact with a woman.
Bernie's success as a "cooler" (he is so unlucky that he breaks other people's winning streaks just by standing close to them) is jeopardized when cocktail waitress Natalie Belisario (Bello) seemingly takes an interest in him, and his luck — and that of those around him — takes a turn for the better. What Bernie doesn't know is that Shelly has paid the woman to seduce him into staying in town. What Shelly doesn't know is that Natalie actually has fallen in love with Bernie, and vice versa.
- Badass Boast: Shelly, to his victim, before and during an epic beatdown.Shelly: "Now listen to me, you little Harvard turd. Lootz is all right. So he's walking out of here with everything he's got coming to him. And if you so much as touch one fucking hair on his fucking head, I'm going to fucking wallpaper this fucking bathroom with your fucking ass, you understand me? Muted tones, isn't that what you said? Huh? Huh? I can't hear you. Wait, wait a minute, there it is... blended in, at a subsonic level, like some kind of mantra: pain, pain, PAIN." (breaks his arm)
- Beauty Is Never Tarnished: Averted with Natalie after Shelly beats her up. Her face is still swollen, bruised and stitched up towards the end of the film.
- Born Unlucky: Bernie is such a magnet for bad luck, he can put an end to any gambler's winning streak just by standing next to them. That's actually how he makes a living.
- Cluster F-Bomb
- Exact Words: When Shelly catches Bernie's son Mikey cheating at the craps table along with Mikey's girlfriend Charlene, he asks Bernie what their lives are worth. When Bernie offers to take in another $150k in debt to spare them, Shelly still breaks Mikey's leg, stating, "150 G's [only] buys their lives."
- Good Old Ways: Shelly and Nicky Fingers long for the days before Las Vegas was corporate. The former is trying to keep his casino old school despite Larry's suggestions.
- The Grunting Orgasm: Bernie gives one during the tune, 'Luck be a Lady Tonight' when having sex with Natalie.
- HeelFace Turn: Shelly, who crippled Bernie both physically and financially to begin with and destroyed him as a man over the years doesn't interfere when Bernie starts a winning streak to buy his future back at the craps table. Shelly takes it a step further by beating down his blueblood assistant when he tries to stop Bernie.
- Like Father, Like Son: Bernie's son Mikey also has the misfortune of pissing Shelly off and having his kneecap shattered due to gambling.
- Male Frontal Nudity: Subverted. We see both Bernie and Natalie lying on the bed complimenting each other about the sex they just had, but when the camera moves downward, Natalie has her hands on his penis.
- Meaningful Background Event: As Bernie pulls into a convenience store parking lot, the car's reflection shows the store's sign "EZ Market" with the last two letters burned out, reading "EZ Mark". We later learn that Natalie was paid by Shelly to be with Bernie.
- Redemption Equals Death: Shelly, after his HeelFace Turn, is shortly whacked by Nicky Fingers.
- Trapped by Gambling Debts: The reason why Bernie Lootz works for the casino as a "Cooler" is because he owes the casino over a hundred thousand dollars in gambling debts.