Film: 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. It plays on cable television a lot.

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.

This film provides examples of:

  • Actor Allusion /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.
  • Awesome McCoolname: Gabriel Caine.
  • Badass Grandpa: Honey Roy Palmer is over-the-hill, but still kicks ass in the ring.
  • Battle of Wits: 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.
  • 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.
  • Career-Ending Injury: Happened to Diggs during his last fight from having been poisoned by Gillon.
  • 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.
  • 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.
  • Hustling The Mark: Fitz in the setup, with the rednecks in the bar.
  • 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.
  • 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.
  • 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.
  • Red Herring: A spectacularly gorgeous Heather Graham plays the sister of Caine's prison buddy. It seems like she and Caine will become an item. They don't.
  • 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."
  • Spoiled Brat: Robby, who gets a classic car from his father only to lose it to Fitz a few days later.
  • 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.
  • Villainous Breakdown: Gillion gradually starts to lose his composure once Honey Roy Palmer keeps on winning each fight thats placed before him, he completely loses it when he lost the bet and when Gabriel out conned him at the end.