Diggstown

"There's two things we never joke about here in Diggstown, Mr. Caine; our boxing and our betting."

Diggstown is a 1992 boxing film starring James Woods, Louis Gosset Jr. and Bruce Dern.

James Woods stars as Gabriel Caine, a conman with a plan to hustle the corrupt city boss of Diggstown, John Gillon, with a daring boxing wager. Louis Gossett Jr. plays "Honey" Roy Palmer, a retired, almost-was boxer who must defeat ten opponents in 24 hours to win millions of dollars. Both sides of the bet try to out-fox the other with various schemes to rig the contest in their favor.

"Caine: You know, Warden, I owe you an apology. When they told me you had blanks in your clip, I didn't know they meant your gun."
 * Anticlimax Boss: Played intentionally as part of The Con.
 * Awesome McCoolname: Gabriel Caine.
 * Badass Grandpa: Honey Roy Palmer is over-the-hill, but still kicks ass in the ring.
 * Battle of Wits: To quote two characters: Never try and hustle a hustler[.] Never con a con-man.
 * The Con: Subverted by the fact that both Caine and Gillon know that the other is trying to hustle them, but make the wager anyway, believing that they will get the upper hand.
 * Deadpan Snarker: Gabriel Caine
 * When the prison warden is holding a gun on him...

"Paoulo: It looks like I finally get to kill you after all. Caine: Well, that's a distinct possibility. But I'd bet, I don't know, four dollars against an hour with your mother that it doesn't turn out that way. (Paoulo punches him in the stomach) You're right. That was insulting. I'm sorry. Five bucks."
 * When the underling of the gangster who's fronting his bet is about to hang him from a tree:

"Roy He seems awful mad.. (beat) Did you tell him he was black?"
 * Ironic Echo: A particularly awesome non-verbal example.
 * Kick the Dog: Gillon holds one boxer's brother hostage, threatening to kill him if the boxer doesn't knock out Palmer.
 * Made of Iron: Honey Roy takes a beating from several fighters in a 24 hour period, only to emerge victorious. Even during one fixed fight, he encourages the fighter to hit him harder to sell the fix, stating, "I ain't made of glass!"
 * Out-Gambitted: Gillon is defeated after a back-and-forth battle of gambits to rig the wager. Realising that he'd been bested by a superior conman, Gillon admits, "You beat me fair and square!"
 * He's still a sore loser, as his next action is to grab the sheriff's gun and try to shoot Caine, only to be stopped by his own son.
 * Shout-Out: When Caine is trying to inspire Palmer against a particularly tough fighter, he gives a little speech acknowledging how tough his opponent is, ending with, "But you remember this! You... are black." Palmer wonders what the hell that means, and Caine admits he was trying to inspire him; "It's a Roots kind of thing." Palmer retorts, "Well, you're shit at motivation." Doubles as a Crowning Moment of Funny.
 * There was an echo of this later on (but it was cut and only appears in one of the trailers). Roy is facing a nightmare challenger from his past.