History Film / Diggstown

* KarmaHoudini: Gillon ends up losing the bet with Caine, his money, his influence in Diggstown, and the respect of his son. He also gets punched in the face. Seems like a pretty satisfying HumiliationConga, right? Except he is guilty of at least two ''murders,'' and he walks away a free man.

* 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.]]

* 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.

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

->'''Gillon:''' ''[[SeriousBusiness 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.

* 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.]]

* 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]].

* CastTheExpert:
** The first boxer Roy fights is a former heavyweight title challenger Rocky Pepeli.
** The referee is legendary kickboxer Benny "the Jet" Urquidez.

* RedHerring: A spectacularly gorgeous Creator/HeatherGraham plays the sister of Caine's prison buddy. It seems like she and Caine will become an item. They don't.

* SpoiledBrat: Robby, who gets a classic car from his father [[spoiler:only to lose it to Fitz a few days later.]]
** JerkWithAHeartOfGold: At the end, even he is disgusted with his father and tells him "You deserved to lose."

* TranquilFury: Honey Roy, during his fight against Sonny.
** As Gillon lampshades, "His mind is at a different place right now"
* VillainousBreakdown: 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.

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

* 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''.

* 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''.

* ItsPersonal: As Honey Roy put it. "It isn't about the money anymore"

* ActorAllusion /CelebrityParadox: 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}}''.

* AnticlimaxBoss: Played intentionally as part of TheCon. [[spoiler:Palmer is barely able to stand after defeating his old nemesis in the final fight, only to learn that he must face ''another'' badass boxer, Minoso Torres. Unbeknownst to him, however, Torres and Caine have already arranged a fix, and Torres lays down after one punch.]]

* TrainingMontage: In the second act.