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->'''Gillon:''' There's two things we [[SeriousBusiness never joke about]] here in Diggstown, Mr. Caine: our boxing and our betting.

''Diggstown'' is a 1992 boxing-themed comedy-drama film starring James Woods, Louis Gossett Jr. and Creator/BruceDern. It plays on cable television ''a lot.''

Gabriel Caine (Woods) is a conman with a plan to hustle the corrupt city boss of Diggstown, John Gillon (Dern), with a daring boxing wager. "Honey" Roy Palmer (Gossett), a retired, almost-was boxer, 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.

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!!This film provides examples of:

* AwesomeMcCoolname: Gabriel Caine.
* BadassGrandpa: Honey Roy Palmer is over-the-hill, but still kicks ass in the ring.
* BatmanGambit: Caine's plot requires a bunch of them:
** Fitz's role depends on Gillon's son accepting his wagers and losing to the point that Gillon will find out and have to accept Fitz's boxing bet to rescue him.
** Caine counts on Palmer joining the plan after it's already underway. Palmer objects to the trope's use, but follows it anyway.
* BattleOfWits: The hero and villain are both hustlers and con-men. The central conflict is essentially a battle of wits to out-con the other and stack the boxing match in their favor.
* TheBet: Caine and Gillon bet on whether or not Palmer can win ten fights in a single day against ten men from the county where Diggstown is.
* BlackAndGrayMorality: Caine is a con man who is trying to win a bet by fixing a bunch of boxing matches. Gillon for his part is thoroughly evil and has no problem committing murder to win that same bet.
* CareerEndingInjury: Happened to Diggs during his last fight from having been poisoned by Gillon.
* CelebrityParadox: Caine tries to inspire Roy by reminding him that he's black, saying, "It's a ''Series/{{Roots}}'' kind of thing." Louis Gossett Jr. was in ''Roots''.
* CheatersNeverProsper: A fighter is disqualified for kicking Roy in the crotch. He goes on hitting the referee, before Roy strikes back.
* ChekhovsGunman: Minoso Torres, the prison fighter seen giving a beatdown to Wolf Forrester in the opening scene, is brought back at the climax, as Palmer's 10th opponent.
* TheCon: 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.
* CorruptHick: Gillon, who has nothing against poisoning and/or killing people to win wagers.
* CurbstompBattle: Sonny, the unfortunate victim of Honey Roy's TranquilFury.
* DeadpanSnarker: Gabriel Caine
** When the prison warden is holding a gun on him...
-->'''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.
** When the underling of the gangster who's fronting his bet is about to hang him from a tree:
-->'''Paolo:''' 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.
* DeepSouth: As always, filled with violent racists!
* DownToTheLastPlay: Partially justified. Hypothetically Palmer could have gotten knocked out by the third boxer or something, but then the movie wouldn't have had a HappyEnding.
* TheDragon: Paolo, who really wants to kill Caine for some unexplained reason, is this to Victor Corsini.
* HangoverSensitivity: Fitz on the morning after the setup. The pills he took when he was husting the hillbillies at cards and pool prevented him from getting intoxicated, but they can't stop the hangover.
* HopeSpot: A rare villainous example when Gillon celebrated a little too soon when Gabriel threw the towel, before Honey Roy crushed his hopes by catching it.
* HustlingTheMark: Fitz in the setup, with the rednecks in the bar.
* InsistentTerminology: Gabriel is a conman, not a hustler. In the beginning, he states that hustlers flee town after scoring, while conman can leave at their leisure. When Gillon thinks that he has Gabriel beat, he chastises him, "Never hustle and hustler," but Gabriel corrects him, "Never con a conman," just before pulling his final con.
* IronicEcho: A particularly awesome non-verbal example. [[spoiler: Gillon signals to a fighter to throw a fight by standing up, straightening his tie, holding a thumb up and then turning it down. Caine does the exact same thing to Palmer's last opponent, Minoso Torres, to let him know it's time to throw that fight.]]
* ItsPersonal: As Honey Roy put it.
-->'''Honey Roy:''' It isn't about the money anymore.
* KansasCityShuffle: [[spoiler: Caine intends to bribe the Diggstown fighters. Gillon suspects this, and brings in Minoso Torres from the prison... who was also bribed by Caine, before the setup.]]
* KickTheDog: Gillon holds one boxer's brother hostage, threatening to kill him if the boxer doesn't knock out Palmer. [[spoiler:He doesn't knock out Palmer.]]
* LoopholeAbuse: Both Caine and Gillon try to use the wording of their agreement to their advantage. Caine insists that a day must be 24 hours and that it must start exactly at midnight, hoping that the farmers wouldn't be used to getting up so early. Gillon insists on expanding the definition of "Diggstown" to encompass the entire Olivair County [[spoiler:to be able to bring in a SuperRinger in the form of Minoso Torres, a prison inmate in the county]]. The time between the verbal and written agreements also makes an appearance, when [[spoiler:Gillon moves another SuperRinger into the town the day before the written agreement is signed, thus allowing him to participate in the fight]]. Additionally, [[spoiler:a fight only starts when both fighters enter the ring, so Gillon forces his son to step up to the ring and leave before entering. Caine and Palmer assume that it counts as a fight, but Gillon uses it to bring in Hagan after Palmer is tired, since he technically counts as fighter #10]].
* MadeOfIron: 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!"
* OutGambitted: Gillon is defeated after a back-and-forth battle of gambits to rig the wager. Realizing that he'd been bested by a superior conman, Gillon admits, "You beat me fair and square!"
* ThePlace
* PlayingDrunk: Fitz in the setup, faking intoxication to win a lot of money from the rednecks in the bar.
* SecondFaceSmoke: One of Palmer's opponents takes a puff on a cigar as he enters the ring and then does this to Palmer. Palmer responds by knocking him out with ease.
* ShoutOut: 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."
* SpoiledSweet: Robby, in spite of being pampered by his crook of a father, is a pretty decent guy. He never shows his father deviousness or corruption, is honestly surprised and appreciative of his father's gift of a car, and ultimately criticizes his father's behavior.
* SuperRinger: [[spoiler:Played twice, for the two last fights. For the ninth, Gillon drafts Hammerhead Hagan, who had moved into the county before the rules were made. The second time, Gillon has recruited Minoso Torres from the prison, which is within the county.]]
* TattooedCrook: Torres, Palmer's last opponent.
* ThrowingTheFight: Gillon does it in the introduction. Caine intends to do it later.
* TrainingMontage: In the second act involving Honey Roy and the opponents Honey Roy was up against.
* TranquilFury: Honey Roy, during his fight against Sonny. As Gillon lampshades, "His mind is at a different place right now"
* VillainousBreakdown: [[spoiler:Gillion gradually starts to lose his composure after losing the bet, snarling at passersby until he goes into a rage and tries to command the sheriff to execute martial law and capture Gabriel's crew in the street as they try to leave. He's rejected, having lost his power. He then grabs the sheriff's gun and tries to shoot Caine himself, only for his son to step in and disarm him, disgusted with his father.]]