“This ain’t about money anymore.”

DIGGSTOWN, released August 14, 1992, is a pretty entertaining meat and potatoes movie, with the meat being a sports movie and the potatoes being a con movie. It’s directed by Michael Ritchie (PRIME CUT, FLETCH) and written by Steven McKay (between HARD TO KILL and DARKMAN II: THE RETURN OF DURANT) based on the novel The Diggstown Ringers by Leonard Wise.

James Woods (BEST SELLER) stars as Gabriel Caine (no relation to RAISING CAIN), a master manipulator doing time in a Georgia prison for selling counterfeit art, now making money on the side helping other prisoners escape. When he’s released he heads to nearby Diggstown with a complicated scheme targeting unofficial ruler of the town John Gillon (Bruce Dern, THE DRIVER). Gillon was once the manager of local boxing legend Charles Macom Diggs (Wilhelm von Homburg, DIE HARD, NIGHT OF THE WARRIOR). Now he manages the small boxing venue Diggstown Arena, but makes enough money to buy his his son Robby (Thomas Wilson Brown, the neighbor kid in HONEY, I SHRUNK THE KIDS) a ’56 Corvette.

Caine gets Gillon’s attention by going to the arena, parking in his spot, sitting in his seat, and being a smart ass (the character and actor’s primary talent) when confronted about it. Meanwhile, Caine’s co-conspirator Fitz (Oliver Platt, BEETHOVEN) is across the street at Nel’s, a bar with Alabama on the jukebox and a Confederate flag on the wall between all the vintage boxing flyers. He proceeds to hustle Robby Gillon and his friends at cards and pool, winning the aforementioned Corvette in the bet.

Jesus christ stop leaning on him, you’re a grown man you know how to balance on your own.

But this is really just the prelude to the real hustle. He defends his actions by asking, “Did I ask you to shoot pool? Did I? Or beg to play poker with you guys? Hell no! I told you I was gonna win! Now you’re all upset ‘cause you didn’t listen?”

Then he quasi-drunkenly bangs his head into the bar’s worshipful portrait of Charles Macon Diggs and starts making fun of it, offending the locals as bait for an even bigger bet. While he’s mouthing off about how Diggs wasn’t that great and “Honey” Roy Palmer (Louis Gossett Jr., also in ACES: IRON EAGLE III that summer) could take on any ten men in town, Gillon Sr. (having been notified about his son losing the car) walks in and (he thinks) calls his bluff.

When Fitz pretends to try to back out of it, Caine speaks up, offering to finance the bet, and revealing for the first time that he’s sitting at a table there. I like that he’s got a drink in his hand, so at some point during all this he not only slipped in unseen, but purchased a drink.

Most of the best stuff is in the first half, when they’re establishing the characters. The Georgians resent Caine as a guy from Florida, and it’s apparently Miami Vice Florida because he dresses flashy, white suits over loud shirts, doesn’t wear socks, makes sure they all notice by constantly putting his feet up in front of them. (This is an image choice, not a comfort one, judging by the scene where he has to soak his feet in Epsom salt.)

I suppose that’s a standard James Woods wisecracking superdouche character, and Roy is standard Louis Gossett Jr. fiercely likable serious badass. He starts out with hair on the sides, which is new, but he shaves for the fight.

You know he’s gonna end up in the ring, but you agree with him not wanting anything to do with Caine (who already failed him and owes him money). Roy turns Caine down while teaching kids boxing at the YMCA, but signals he kinda wants to do it by inviting him for dinner. I like that his wife Mary (Gossett’s real wife at the time Cyndi James Gossett, VICE SQUAD) doesn’t smile or say a word to either of them, obviously knowing what’s going on, that she disapproves, and that she can’t stop him. That night Roy knocks on Caine’s boarding house door and storms in angrily calling him a sonofabitch, which means yes.

He’s got all the Gossett charisma you want, he gets very sweaty, has some good training montages. He makes any movie better, and this time he gets to punch people too. Platt just becomes a sidekick or comic relief background character after his one man show in the bar, though.

As I’m sure you’re aware, Dern is also reliable playing this kind of prick and giving more personality to the smugness than most actors could manage. My favorite illustration of the character’s shittiness is the scene where he’s hunting birds while sitting in a convertible, wearing a nice suit and tie.

One character we don’t see enough of (spoiler, but you’ll figure he’s not long for this world, or at least I did) is Caine’s friend in prison who comes from Diggstown and gives him all the info. Wolf Forrester (Randal “Tex” Cobb, BLIND FURY) is supposed to get out in two weeks but still begs Caine to visit his dogs for him and give them a shirt with his smell on it. Of course you gotta like that character!

Though he tries to hide that he knows Wolf, Caine stays at the boardinghouse belonging to his sister Emily (Heather Graham, DRUGSTORE COWBOY), which is where the dogs are. Caine (age 45) immediately gives off boner signals when he sees Emily (age 22), and the camera emphasizes every time she leans over in her Daisy Dukes. She seems open to him at first, which is terrifying, and I was relieved that they never hook up. I wasn’t surprised to read that in the book (where she’s a teenager!) they have a relationship, because here the character doesn’t seem to have much purpose.

Of course the back half of the movie is dominated by the boxing. That’s a little more of a been-there-done-that feeling than in the earlier stuff, but it has plenty of highlights. Like, it’s extra fun to see Roy punching out the opponent who calls him an n-word, because he’s played by future Jesus/QAnon-cultist/HIGHWAYMEN star Jim Caviezel. And there’s a really badass part where Caine, worrying about the safety of Roy, throws in the towel – but Roy catches it and angrily tosses it back.

Oh, and hey – I recognize that ref.

(It’s Benny “The Jet” Urquidez of WHEEL ON MEALS fame. He was also the fight trainer.)

But the main novelty of the boxing event is that it’s partly a matter of over-the-hill Roy going the distance with ten younger fighters in a row, and partly a cheating/dirty tricks battle between Caine and Gillon. Caine has paid a bunch of the fighters to take falls, and also gives a guy a laxative causing him to lose due to farting. But he still counts as the good guy because Gillon’s tricks involve murdering two innocent people (whether or not Caine should’ve been willing to back down to prevent it). Gillon also has a secret (never exposed to the town at large) that he fucked over everybody’s hero Diggs.

Because it’s a con movie there are some fun reveals where Caine has been ahead of us and the others the whole time. Gillon also pulls one of these maneuvers. There’s a little mention early in the movie that Emily has a new tenant moving in to her basement but hasn’t met him yet. I figured I missed something and then forget all about it but it turns out Gillon moved Roy’s seemingly unbeatable rival Hammerhead Hagan (Willie Green) there to make him a resident and therefore eligible for the bet. When Caine finds out he sputters and complains – I feel like he doesn’t give Gillon enough credit for the gratuitous audacity of having him literally living under Caine’s nose. It could’ve been anywhere in the county, but they chose the basement below Caine. If he could take a step back and look at it objectively he’d definitely appreciate that touch.

I don’t find Caine as charming of a dickhead as we’re supposed to, but Gillon is worse, and it’s fun to watch him totally lose his shit when it’s over. He gets into a pathetic tantrum argument with his stooges behind the popcorn stand, grabs a cop’s gun and fires it into the ceiling, total chaos. The best part is that after that, when he slaps his son, you hear people gasping.

DIGGSTOWN got mixed reviews and lost money at the box office. I’m sure many people enjoyed it on cable, though. It seems pretty perfect for that forum.


Since I brought it up in my review of BLOODSPORT 4: THE DARK KUMITE I want to note that this has another example of a sarcastic reference to Club Med, the brand name for paradise in the ‘80s and ‘90s.


2. “Only the best comes in Glass!”

I guess this was a slogan for making things out of glass? I found the logo on many vintage keychains, t-shirts and shot glasses that are available for sale online. I don’t really get it, but I like it.


This one may or may not be a reference to an MC Hammer lyric. If you can’t tell from the picture, the hat is shiny silver. He wears it throughout the movie (sometimes backwards) but later he’s found badly beaten and he mutters “I lost my hat. Somebody find my hat.” I don’t blame him!

This entry was posted on Thursday, September 22nd, 2022 at 10:02 am and is filed under Comedy/Laffs, Crime, Reviews, Sport. You can follow any responses to this entry through the RSS 2.0 feed. You can skip to the end and leave a response. Pinging is currently not allowed.

7 Responses to “Diggstown”

  1. I know it’s more loaded now but this is still a great crowd pleaser with some really ridiculous ways of dealing with racism.

  2. So… While Raising Cain proved to be a great object example on losing an audience, this proved to be a great object example on winning one




    during a key scene at the end involving James Wood’s hand, the audience e x p l o d e d in a manner I’ve never seen before or since. Like, 80-year-olds who were barley able to walk into the theater JUMPING to their feet and cheering type of exploding. It was wild


  3. I loved this one when it came out. Full of crowd pleasing moments, and I always enjoy con men movies.

    I remember they had a sneak preview for this a week before opening in my area, but they didn’t advertise the title. They just said it was an exciting action comedy. Always thought that was a cool way to build hype for a flick folks might not know/care about beforehand. I missed it then but caught it a few weeks later. Never saw anything like that since.

  4. This was a strong word of mouth Movie. Though never a hit, those who saw it got really into it. I remember a story of a theater worried it was another New Jack City violence incident but it was just people cheering and counting opponents out. I didn’t get one of those crowds but I saw it with my dad and we liked it enough.

  5. By the way, Wilhelm von Homburg aka Norbert Grupe was indeed a real boxer and a quite infamous one. Legendary is his appearance on national television where he remained silent, because the host was quite critical of Grupe’s work and private life. Because of this and some other things, he later got a lifelong ban from the German boxing comission, that he could successfully repeal.

    Das aktuelle Sport-Studio: Interviewversuch mit Boxer Norbert Grupe (ZDF 1969)

    Aus der unauthorisierten Reihe "Pannen, Pleiten und Pech aus 59 Jahren ZDkläfF" ein nicht ganz unbekannter Ausschnitt aus der Sendung "Das aktuelle Sport-Stu...

  6. This was a strong word of mouth Movie. Though never a hit

    According to Woods, when MGM saw how huge the test scores were they figured word of mouth would be so strong, they could save some money on promotion. He stated that he noticed the theater where the premier was being held had no Diggstown posters anywhere, and when he asked about it, he was told “They’ll ship when it opens”. Of course his next question was “How the fuck will people know it’s opening?”

    Personally speaking, I know that I saw a trailer or two very early in the summer, but didn’t know it had opened until I noticed it at second-run (where I saw it). That said, I wasn’t watching a ton of television at that point, so there could have been TV ads.

  7. It took me a while to get that I’ve actually seen this one, but under the name MIDNIGHT STING. Can’t remember much, but I think I liked it.

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