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Film / Diggstown

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Gillon: There's two things we 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 Bruce Dern. 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.


This film provides examples of:

  • Awesome Mc Coolname: Gabriel Caine.
  • Badass Grandpa: Honey Roy Palmer is over-the-hill, but still kicks ass in the ring.
  • Batman Gambit: 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.
  • Battle of Wits: The anti-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.
  • The Bet: 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.
  • Black and Gray Morality: 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.
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  • Career-Ending Injury: Happened to Diggs during his last fight from having been poisoned by Gillon.
  • Celebrity Paradox: Caine tries to inspire Roy by reminding him that he's black, saying, "It's a Roots kind of thing." Louis Gossett Jr. was in Roots.
  • Cheaters Never Prosper: A fighter is disqualified for kicking Roy in the crotch. He goes on hitting the referee, before Roy strikes back.
  • Chekhov's Gunman: 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.
  • 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.
  • Corrupt Hick: Gillon, who has nothing against poisoning and/or killing people to win wagers.
  • Curbstomp Battle: Sonny, the unfortunate victim of Honey Roy's Tranquil Fury.
  • Deadpan Snarker: 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.
  • Deep South: As always, filled with violent racists!
  • Down to the Last Play: Partially justified. Hypothetically Palmer could have gotten knocked out by the third boxer or something, but then the movie wouldn't have had a Happy Ending.
  • The Dragon: Paolo, who really wants to kill Caine for some unexplained reason, is this to Victor Corsini.
  • Hangover Sensitivity: 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.
  • Hope Spot: 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.
  • Hustling the Mark: Fitz in the setup, with the rednecks in the bar.
  • Insistent Terminology: 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 a hustler," but Gabriel corrects him, "Never con a conman," just before pulling his final con.
  • Ironic Echo: A particularly awesome non-verbal example. 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.
  • It's Personal: As Honey Roy put it.
    Honey Roy: It isn't about the money anymore.
  • Kansas City Shuffle: 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.
  • Kick the Dog: Gillon holds one boxer's brother hostage, threatening to kill him if the boxer doesn't knock out Palmer. He doesn't knock out Palmer.
  • Loophole Abuse: 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 to be able to bring in a Super Ringer 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 Gillon moves another Super Ringer into the town the day before the written agreement is signed, thus allowing him to participate in the fight. Additionally, 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 Torres after Palmer is tired, since he technically counts as fighter #10.
  • 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. Realizing that he'd been bested by a superior conman, Gillon admits, "You beat me fair and square!"
  • The Place
  • Playing Drunk: Fitz in the setup, faking intoxication to win a lot of money from the rednecks in the bar.
  • Second Face Smoke: 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.
  • 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."
  • Spanner in the Works: The fight with Hagan is the one on which the whole fight hinges. He's Roy's old nemesis and an even match for him even on a good day, he's fresh while Roy is fighting tired after besting 8 opponents already, and it's one of the few fights that isn't fixed. Neither Caine nor Gillon knows how this fight will go. Everything rides on whether Roy has enough left to go the distance against the toughest opponent he's had all day. Afterwards Caine tells Roy, "What you did today... couldn't be done."
  • Super Ringer: 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.
  • Tattooed Crook: Torres, Palmer's last opponent.
  • Throwing the Fight: Gillon does it in the introduction. Caine intends to do it later.
  • Training Montage: In the second act involving Honey Roy and the opponents Honey Roy was up against.
  • Tranquil Fury: Honey Roy, during his fight against Sonny. As Gillon lampshades, "His mind is at a different place right now"
  • Villainous Breakdown: 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.
  • Your Mom: Caine offers to make a bet, "Four dollars against an hour with your mother" to Paolo.

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