Diggstown Might Be A Favorite You Won’t See Coming

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The sports comedy has, time and again, proven to be a hit film genre back before things in the cinema went super-serious. They were almost never good movies, never really well-reviewed films, instead preferring to be a feel-good vehicle over a true work of art. Diggstown, the 1992 movie starring a young James Woods and Louis Gossett, Jr. in front of the cast, is one such movie that isn’t so deep.

Diggstown sees Gabriel Caine (the con man played by James Woods) released from a prison in Georgia, already ready to get to work scamming his next victim. Caine and his partner, Fitz (played by Oliver Platt), travel to Diggstown, a city not far from the prison obsessed with boxing, ran by a man named John Gillon, who was once the manager of boxer Charles Macom Diggs, who the city is named after.

Caine and Fitz’s next scam involves the claim that Diggs once knocked out five boxers in one day, claiming that they know someone who can knock 10 boxers out in the same time.

They make a bet for $100,000 with Gillon, and seek out a friend they have, Palmer, a former professional boxer who is 48 years old and actually manages a YMCA. Palmer eventually agrees with the con, and they get a loan shark to back the bet.

Caine finds out that Gillon is actually a sketchy guy, drugging Diggs to lose a fight and collect the winnings on a bet for his opponent. Caine gets Gillon to put all of his money and assets on the line, totaling $1.5 million all in all. The fight is on, with Palmer having to beat 10 men in 24 hours.

The first five boxers are beaten, with one of them even getting murdered by Gillon for not winning against Palmer. Gillon’s own son, a boxer, forfeits the match. The rest of the boxers are beaten as well, with Palmer barely defeating all of them. But because Gillon’s son didn’t fight in the ring, it allows Gillon to introduce a hulking replacement who, long story short, has already previously been bribed by Caine long before the fight, expecting this development to happen. The last fighter takes a dive for Caine and Palmer, allowing them to win the bet against Gillon.

Straight out the gate, Diggstown is a movie whose reviews are split straight down the middle. It has a 54% review rating over at Rotten Tomatoes, and it seems that a good number of writers and viewers are both for and against it. It’s not hard to see why Diggstown is polarizing: for those who want a straight up feel-good movie with a bit of an edge, then this is totally fine. But for those who take films too seriously that they can’t suspend disbelief at all, then Diggstown has to work harder.

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Diggstown is by no means a spectacular movie, but it has heart, even in its messed-up con man with a heart of gold way. The jumpy, anxious brand of performances James Woods, leading the cast, is known for appears in this movie in full force, and it’s great. Oliver Platt as his partner is also so smooth that I wouldn’t be surprised if they were real con men. Perhaps it’s really hard to get into the fact that a washed-up pro boxer could take on 10 men in one day. Even watching the trailer, it seems to be a preposterous buy:


But Louis Gossett, Jr. plays the role to a tee, buying into his ridiculous situation and getting gritty in there, even if he actually isn’t the one taking all the hits. Bruce Dern is a perfect villain in this movie, as the self-made villainous millionaire. If everything in Diggstown seems like an entire act to prop up just one major sports cliche, then it doesn’t really matter that much as director Michael Ritchie makes the most out of the trope established by films like the Rocky series and does it well.

Diggstown makes the most out of the triumphant underdog sports trope by not actually going down that path. Of course the movie knows it’s ridiculous for a 45-year-old former boxer to even win against 10 men, with varying levels of training and experience, by knockout.

So the way it gets there isn’t always the direct, honest way, and the way it wins in the end is never by the power of sheer strength and athleticism. At the end of the day, the protagonists of the movies are con men, so the con men have to win the best way they know how, which is by scamming. The cleverness of it all is probably what gets Diggstown its better reviews.

If you’re the type of movie watcher who likes to go see old, underrated movies just to watch something new, then Diggstown is a great movie to rent for a night. If you can find it on your favorite streaming service, then that’s even better. It’s really just a throwback to a time when movies, sports movies, were much simpler. You may not love it too much, but that’s all right. It’s a film that’s just asking to be liked.

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