Bullet Points: Diggstown (1992)
Since watching it more than twenty years ago, Diggstown has always had that “comfort food” feeling to me. I’m already a big fan of the “sweet science” and it’s hard to go wrong with insanely talented actors like James Woods and Bruce Dern, but the real reason I re-watched Diggstown recently was because of the legend Louis Gossett Jr. Seeing him not long ago in Iron Eagle was like catching up with an old mentor years later. I just feel like I have so much I could learn from him.
Synopsis: Recently released from prison, con man Gabriel Caine (James Woods) cooks up another scheme in the small town of Diggstown. This time, he convinces an aging boxer to face off against 10 men in a 24 hour period in order to wrestle away a fortune from a local crooked businessman.
- It’s all about who you know: It is so refreshing to put a movie on and instantly recognize actors. It’s one of the beauties of watching a movie that’s 30 years old. It’s pretty clear right away that Randall “Tex” Cobb of Uncommon Valor fame isn’t going to be a massive character in this film but it’s still comforting to see him. We also get to meet James Woods’ Gabriel Caine. He’s a con man who is serving out his last couple of weeks in prison by helping others escape for money. That shows he covets money above all else and isn’t afraid to take a risk for it.
- Diggstown: The small town is essentially run by Bruce Dern’s John Gillon. He owns the local boxing gym and a whole lot more throughout the town. Boxing pretty much IS this town since it’s named after a former boxing great Charles Macum Diggs. Caine knows that and uses boxing to unleash a massive bet in order to win a boatload of money from Dern’s Gillon.
- The stage is set: The plan pretty much works perfectly even though no one really believes that James Woods and Oliver Platt’s Fitz are complete strangers. They set up an bet that pits “Honey” Roy Palmer (Louis Gossett Jr.) versus any ten men who live in the town. Later, Gillon fights to have the bet include anyone from the county which it’s located in and you just know that is going to have some massive repercussions.
- True con men: In true con man fashion, we slowly start to see the plan unravel and evolve over the course of the film. A good portion of the film turns into Roy training for his marathon fight and the rest of his team trying to find out not only who he is fighting, but how much they’ll have to pay to get each man to take the dive. What is most important to see while watching at this point is the relationship between Woods and Gossett Jr. and how their priorities change throughout the final act of the film.
- You can’t shit a shitter: As the fights begin, Roy takes over and either beats the hell out of each man, or simply carries them until it’s time for them to drop. The interesting thing about the fight is that Roy might have been good enough to take all 10 of them even without paying some off. Either way, Caine and Gillon continue to up their bet until it becomes a life or death situation for Caine and a risk to everything that Gillon has built. It’s also a great bit of scenes where Roy beats the crap out of some guys, did I mention that?
- “Heroes” and “villains”: The movie doesn’t start with a “hero”. Woods and his friends are all a bunch of con men who are out to make a buck but slowly turn into good guys based on how much of a dick that Gillon is. Especially as the fights go the way of Caine and friends, Gillon turns to more and more evil ways of getting what he wants. My favorite scene has to be when Dern is praying with his fighters before the big fight and he is just filled to the brim with shit. It’s basically spilling out of his mouth as he talks.
The Verdict: You already know that I love this movie. Louis Gossett Jr. doesn’t get enough respect and Oliver Platt is always one of my favorite parts of any movie he’s involved with. We also have a young Heather Graham who plays the sister of Tex Cobb and it’s a little surprising they didn’t shove her in a sexual relationship with Caine by the end. Speaking of Caine, Woods is fantastic in the role and we get callbacks from his old friends and enemies in the prison while still pushing the story forward and extending the runtime to some ridiculous length. Boxing is such a great sport and maybe the best sport-to-film success ratio of any sport out there. Diggstown is such a fun watch and it never gets old for this guy.
