A gambler, fresh out of prison, and a beautiful hooker find themselves caught in an underground scheme that's spinning wildly out of control.

A doctor is driven into an investigation of sinister goings-on at a horse race track by his mystery writer ex-wife.

A slice-of-life story unfolds inside The Florentine, a bar in a Pennsylvania steel town whose brightest days are behind it, leaving behind many of life's disillusioned "losers." Its owner, Whitey (Michael Madsen), is deep in debt to the town's loan shark, Joe McCollough (Burt Young), and desperate for a path forward which won't cost him the bar. His sister, Molly (Virginia Madsen), is days away from her long-awaited nuptials, and then her former fiancé, Teddy (Tom Sizemore), shows up in town for the first time since leaving her at the altar years before. Ne'er-do-well Billy Belasco (Jim Belushi) runs a con on Frankie (Luke Perry) to steal the money for the wedding caterer, while long-time regular Bobby (Chris Penn) becomes a patron-cum-inhabitant as he hides from his fast-crumbling marriage to Vikki (Mary Stuart Masterson). Every plot in this multi-layered story seems to be at its nadir just as a pair of unlikely heroes emerge out of the backdrop to turn everything around.

Four college friends become small-time bookies, only to find their world spinning dangerously out of control when their greed attracts the attention of organized crime.

A young gambler makes a large, risky bet on a horse race. When the odds turn in his favour, more than one party has sudden interest in the winning betting slip, and they'll do anything to get their hands on it.

"In the Gay Nineties New York had grown up into bustles and balloon Sleeves ... but The Bowery had grown younger, louder and more rowdy until it was known as the 'Livest Mile on the face of the globe' ... the cradle of men who were later to be famous.