Boxing Movie Review: Diggstown has earned its status as a minor cult favorite

With the boxing world still on hold due to the COVID-19 pandemic across the world, we at Bad Left Hook continue to look for various ways to keep the show going without any actual fights to cover at the moment. We’ve got ourselves a little old Movie Club, a good old fashioned gathering of folks to talk about movies; being specific for this case, boxing movies.

The BLH Movie Club will chug on today with Diggstown, a 1992 cult favorite (kind of a cult cult favorite) among boxing fans. As mentioned in the review for The Great White Hype, Raging Bull was actually next on the list after Rocky, but the Scorsese classic is just really heavy, and there’s enough “really heavy” in the world at the moment that I just haven’t wanted to watch it again, even for A Project.

We’ve had a few people request Diggstown, and I haven’t seen this in at least 25 years, probably, but I also remember liking it, so this is today’s pick. The movie was a cable staple for some time, and you can still stream it through Cinemax right now, which is how I watched it this time.

Note: There are spoilers for plot points and whatnot in the review. This is a 28-year-old movie, after all, but if you want to avoid all spoilers but still get quick thoughts, you can skip down to the bottom for the rating and the bits after that. Otherwise if you haven’t seen it, you might be better off watching the movie and then coming back to read the review. Plus then you can discuss it with us!

Diggstown (1992)

98 minutes. Directed by Michael Ritchie. Screenplay by Steven McKay, based on a novel by Leonard Wise. Starring James Woods, Louis Gossett Jr, Bruce Dern, Oliver Platt, Heather Graham, Randall “Tex” Cobb, Thomas Wilson Brown, Duane Davis, David Fresco, Willie Green, Orestes Matacena, Kim Robillard, John Short, Jim Caviezel, and Marshall Bell.

Diggstown opens on a prison fight in Georgia, rowdy inmates forming a circle as two men pound one another. One of those men is Wolf Forrester (Randall “Tex” Cobb), and Gabriel Caine (James Woods) looks on for a bit, then sneaks away to help another inmate escape during the ruckus. It turns out this isn’t the first time he’s done this; the warden (Marshall Bates) notes that it’s the fifth escape since Caine has been locked up, and vows to find out how Caine is doing this before his release in a week.

Wolf, meanwhile, is beaten down by Torres. The amiable country boy was fighting on Caine’s behalf, and it didn’t turn out his way, but Caine pays him what’s owed, and Wolf insists to Caine that he is a good friend. When Caine does get released, the warden having found out nothing, Wolf — weeks away from his own release — begs Caine to take one of his shirts and visit his dogs, so they can catch his scent on it. Caine agrees, with some reluctance.

While still inside, we see Caine meet up with Fitz (Oliver Platt), a con man partner visiting and going over the details of their coming scene in nearby Diggstown. Fitz has some concerns that they’ll have to find a way to rush out of town as soon as it’s done, but Caine just smiles.

“You know the difference between a hustler and a good con man?” Caine asks his friend. “A hustler has to get out of town as quick as he can, but a good con man? He doesn’t have to leave until he wants to.”

The setup in Diggstown begins. On one side of the main street in town, Fitz drinks all night and cleans out a local card game, then keeps winning money in billiards bets. Across the street, there’s a small boxing club. We meet John Gillon (Bruce Dern), who manages the club and, according to son Robby (Thomas Wilson Brown), “is Diggstown.” We will come to learn that’s true; Gillon owns most of the property in town. He gives his fresh-faced teenage son a 1958 Corvette as a present.

Caine, meanwhile, meets with crime boss Victor Corsini (Orestes Matacena) in Miami, taking out a $500,000 loan before joining Fitz back in Georgia. There, he visits the boxing club and gets into a charismatic movie conversation with Gillon, each man trying to one-up the other. When Caine puts down a $2,000 bet on a fight happening in the ring, Gillon openly fixes the result — with a sparse attendance, he simply whistles, calls out a fighter’s name, and gives him the thumbs down. The fighter goes down on the next punch, and Caine is out two grand.

Fitz and Gillon the younger get into a billiards bet over pink slips, which Fitz wins. The locals accuse Fitz of hustling them, but he reminds them that he very openly told them at the start that he would take all their money if they pushed him into gambling. He then takes a crack at local boxing legend Charles Macum Diggs, a big promotional portrait of the man still hanging on the wall of the tavern. Diggs is said to have put down as many as five men in a day. Fitz counters by saying that he’s seen “Honey” Roy Palmer do the same. “The most underrated heavyweight of modern time,” Fitz says, boasting that even today, Palmer could take any 10 Diggstown men in a single day.

Metro-Goldwyn-Mayer

Father Gillon is alerted and wanders over to see what’s going on, and engages Fitz in the bet. Caine backs Fitz, the two of course claiming to not know one another, Caine claiming to not even know who “Honey” Roy Palmer is. The bet is made, with the crime boss Corsini named as the neutral party to hold the money in escrow.

The next morning, Fitz finds out that Caine hasn’t even talked to Palmer, the actual fighter in this plan, and Caine has to head to Texas to fetch him. “Honey” Roy (Louis Gossett Jr) is a balding, middle aged man now teaching boxing to kids at a local YMCA. He is not happy to see Caine, as Caine stopped their last fight together and cost Roy $92,000; he tells his old partner that he’s now “off the con,” and Caine pretends to accept this. That baits Roy just enough to get the fighter to invite his old friend over for dinner, and after that, Palmer gets the itch, and the con is on.

Back in Diggstown, Gillon and his team research Palmer and find out that now 48, he hasn’t had a recorded fight in 20 years. He’d only lost two times, to a fighter named Hammerhead Hagan. Everyone but Gillon is confident in success, but Gillon is aware of the game being played, and points out that records don’t show what we’ll actually be seeing: cash fighting, which is what Palmer has surely been doing for much of the last 20 years.

“You fellas better remember,” Gillon warns his lackeys, “this is a man who knocks people unconscious with a single blow. I consider any such man extremely dangerous, even at 48 years old.”

Roy gets to train in a barn on one of the only bits of land in Diggstown that Gillon doesn’t own, a farm where Charles Macum Diggs used to work, now living close by in a sort of vegetative state. Caine also fulfills his promise to talk to Wolfe’s dogs, and meets his friend’s sister Emily (Heather Graham). She quickly sniffs out the scam, but doesn’t say anything to anyone else.

A number of rules are set at a meeting between Caine and Gillon’s team. Two of the fighters, teenage Robby Gillon and his friend Billy Hargrove, are allowed to wear headgear. That’s part of a negotiation where Caine agrees to let any man residing in Olivair County on that day, with proof, to take part. Caine fears ringers, and this sets his mind at ease.

You get some training montage stuff, of course. Old Roy pulls a tractor and runs on the farm land. He sees Charles Macum Diggs sitting on his porch, and one day even goes to talk to him, or at him, as it winds up. Local Buster (John Short) is being paid by Gillon to spy on Diggs and time his runs, but Caine convinces Buster to fudge the numbers.

Roy asks Caine what really happened to Diggs, and Caine admits that Gillon had Diggs drugged during his last fight, but that miraculously, the fighter went the distance and took a horrible beating. It was that Diggs loss that gave Gillon his little backwoods empire. Fitz is able to gather information on some of the fighters, and the Busby brothers, Hambone (Duane Davis) and Slim (Raymond C. Turner) are bought off to take dives.

Shortly after Caine tells Roy what went down with Diggs, Wolf, meant to be released from prison, is found dead in a box on the sidewalk in town. Caine tells Emily that Wolf was the one who found out the truth about Diggs and Gillon, and thus was set up and sent to prison by Gillon. Wolf was to be a full partner in Caine’s plan to take Gillon down, and Emily helps in the planning from there, with Caine making sure Wolf is given a proper sendoff with a beautiful funeral.

Fight night arrives, starting just after Midnight on a Saturdy. Fitz gets the list of fighters from Buster, while Gillon gives his group their strategies. Each of the first five are given a particular task to execute in combined attempts to weaken Palmer — bust up the eyes, soften the body, etc. — for the first two rounds of their five-round bouts; after two rounds of doing their jobs, they are free to go for the victory and the bonus money that comes with it.

Gillon ends the meeting with an all-hands prayer circle. “Dear Lord,” he begins. “Give us the strength and courage to tear this man limb from limb.”

The small gym is packed with everyone in town, even Charles Macum Diggs, who looks down from the balcony in his wheelchair. He didn’t say anything to Palmer when they’d met at Diggs’ home — he probably couldn’t — but he could understand, and he’s here to see what happens. Everyone is betting, including Caine and Gillon making a hefty personal wager with one another, which increases throughout the run of fights.

The first five fights, of course, go Palmer’s way. One of the bought off Busby brothers, the younger Slim, is second up and the nervous youngster simply does now know how to throw a fight without Gillon catching on to what’s happening. Young Billy (Jim Caviezel) doesn’t get much help from his head gear, and is a bit tuckered out, having been set up with some entertainment to tire him out coming into the fight. When Palmer offers the kid mercy, the young man goes racist, and Palmer destroys him with a single right hand to the body.

Once Gillon quickly uncovers the Busy brothers’ dishonesty, having found money in Hambone’s truck, he has Slim captured and will murder him if Hambone doesn’t beat Palmer. Hambone gives his legitimate best effort and puts some real hurt on Roy in the process, but he just isn’t good enough to beat him. When he gets counted out, he staggers to his fee tand races to the back to find Slim murdered, with Caine and Palmer behind him. Roy does his best to console Hambone as Gillon arrives and reads the “suicide note” left in Slim’s trunks.

A break is taken before the second set of fights, and Palmer and Roy and Fitz decide this is no longer just about a big score — their plan is to flat-out gut Gillon financially, to ruin him for good. Before the fights resume, double agent Buster is found badly beaten but alive, stuffed in a locker in Palmer’s dressing room. Caine goes to Gillon and offers a $1.5 million bet, with Corsini backing it — the mobster will either win or get to kill Caine, both outcomes appealing to him. Gillon agrees to put up all of his money and property in town, taking the bet.

Palmer’s demeanor has changed in fight six, as he destroys a cocky local named Sonny (Jeremy Roberts) with one punch. Young Robby Gillon is scheduled to go next, but his father orders him to simply walk to the apron, look Palmer in the eyes, and then leave. Robby tries to refuse, but ultimately does as ordered by his father.

After a couple more fights that get a little rough — a bar brawler kicks Palmer in the nuts, which leads to a terrible beating dished out by Roy, and then the monstrous Tank manhandles Palmer before being knocked out — we arrive at the big final fight.

Who is it? Well, who else besides the aforementioned Hammerhead Hagan, the one man Palmer couldn’t beat 20 years ago? Hagan is younger enough than Palmer that it makes a big difference, and he’s a real fighter in shape, not some local tough guy.

Metro-Goldwyn-Mayer

Hagan pounds Palmer to the point that Caine wants to stop the fight in the corner, which Palmer won’t let him do again. The fights up to now had their little moments, but this one is the first one where we see some really cool fight cinematography and choreography; this is a smart production tactic, because it reinforces the idea that this one, compared to the others, is a sincerely dangerous fight for Roy. It’s a war between two professionals who know what they’re doing, not just Palmer doing his best to take down a series of wannabes who hope he’s gotten tired enough to fall.

There’s a great, great cornball moment where Caine does throw the towel in, but Palmer catches it and dramatically throws it back out of the ring. All of this happens in slow motion, and Roy’s throw is unleashed right when an electric guitar squeals on the soundtrack. You can’t beat that.

Palmer’s heart outlasts Hagan’s, and he knocks his old rival out. With Caine, Palmer, and Fitz celebrating, Gillon notes that that wasn’t 10 fights, but nine. Robby never entered the ring, and thus his forfeit was not official.

Palmer has one more man to beat, and it’s Minoso Torres (Alex Garcia), the inmate we saw pummel Caine’s friend Wolf in prison at the beginning of the movie. Torres is accompanied by Warden Bates, a friend of Gillon’s.

“Never try and hustle a hustler,” Gillon says, looking Caine dead in the eyes.

But as Torres whales away on an exhausted Palmer, Caine repeats Gillon’s move from earlier: he whistles, adjusts his tie, turns is thumb down, and Torres takes the dive on one shot from Palmer.

“Actually,” Caine tells Gillon, “I believe it goes, ‘Never con a con man, especially when he’s better than you are.’”

Distraught and ruined, Gillon tries to get his now-former subordinates to set up roadblocks or whatever, and pulls a policeman’s gun. His son stops him from shooting anyone, and Gillon slaps Robby down. Palmer catches his arm before he can get another shot in on the body, and holds the ex-town czar for Hambone to knock out cold.

We end with Roy and Caine in the empty gym together, having beaten the odds. They get in a last line each, and then it’s over.

Rating: 3.5/5

Diggstown is not a Great Film. In many technical ways, it’s not even a very good movie. But goddamn, is it fun, and sometimes that’s all a person really wants. I’d liked the movie as a kid, but wondered if it would hold up to me as an adult, and it does. I recognize the flaws and don’t really care.

You’ve got Woods and Dern, two great veteran actors, just chewing scenery throughout, sharing these fantastic, melodramatic glares, while Gossett, another great veteran actor, puts in a more subtle, reserved performance as the old fighter. The supporting cast do their jobs well enough, rounding out everything out with small and memorable roles, particularly the opposing fighters; each of them has a distinct little personality, as do their fights.

Dern in particular is incredible here, not in an Oscar-winning sort of way — he’s been plenty capable of that throughout his career, of course — but in that B-movie villain way. He knows the movie he’s in, and doesn’t shy away from it at all. The one thing I truly remembered for the decades since I last watched this movie was the way he held his hands while watching the fights ringside, C. Montgomery Burns style:

Metro-Goldwyn-Mayer

Excellent.

It’s a thin story and there’s not a ton of meat on the bones. Every little twist makes enough sense but lacks any real impact. This is not a deep film, there are no real subtleties to it, no real nuance. It is lightweight entertainment, even considering the violence and whatnot, and it thankfully never really tries to be much more. If it had, it might have truly stunk. Since it doesn’t, it gets to trade on “being what it is.”

Diggstown was a box office flop, but as I said before, seemed to get a bit of a second life on cable through the rest of the 90s. Also known as Midnight Sting, it found at least a small audience, and the requests for me to add this one to the pile are enough to tell me that that small audience still thinks of this movie quite fondly.

If you’ve never seen it and aren’t looking for any big or meaningful exploration into, well, much of anything, but you’d like to see a wily con man and a wily old fighter take on a cartoonish shitheel, you can’t do much better than this.

BLH Boxing Movie Rankings, as of now:

1. Fat City (1972) 4.5
2. Rocky (1976) 4.5
3. Diggstown (1992) 3.5
4. The Harder They Fall (1956) 3.5
5. The Great White Hype (1996) 2.5