Retro Review – Midnight Sting (1992)


‘Midnight Sting’ or as it’s probably better known in the US ‘Diggstown’ stars James Woods as a fast talking con-man looking to pull off a big hustle against an evil man.

Set in the fictional Diggstown, Gabriel Caine (James Woods) a recently released ex-con sets his sights of taking down the unspoken ruler of a small town who is responsible for his friend losing his life.

The con in question that he sets up is a wager that one boxer ‘Honey’ Roy Palmer (Louis Gossett Jr.) can defeat ten men in 24 hours inside the ring. Oh and he’s almost 50 years old and retired……what could go wrong!

Main Hook

This is a great movie! From the opening scenes we get to witness how the fast talking sleek Gabriel runs hustles within the prison and from there the film entertains at every turn. Part boxing flick (think Rocky) and part con thriller (think Oceans Eleven) the movie takes twists and turns where you’re never quite sure who will come out on top. As the stakes get higher so too does the drama.

James Woods is expertly cast as Gabriel and his ease at playing a hustler is entertaining throughout. There are moments where the film goes a little dark and the tone becomes more serious than just one-up-man-ship and it’s here that James Woods shines, losing his usual cool demeanor to show a more morally righteous side. His reasons for taking down the bad guy are sincere and played out well making him slightly more complex than just a con man trying to win big money.

The Bad Guy

Credit where it’s due, John Gillon the town mogul (played by Bruce Dern) is an excellent villain. He loves to gamble and will stop at nothing to win. Believing himself to also be a con man and smarter than most, it’s almost delightful to see him fail. Bruce Dern is an amazing actor and he chews up each scene he is in. He truly embodies a nasty greedy man who feeds off power and corruption and will stop at nothing to win. His softer side only comes out when he’s trying to protect his son (Jim Caviezel) but even then his actions only help to showcase his flaws. A very well written bad guy through and through!


Good Chemistry

It would be remiss of me not to mention the chemistry between James Woods and Louis Gossett Jr. These two bounce off each other like they’ve known each other all their lives. The smart snide comments and banter back and forth gives a fresh energy to each scene they’re in and adds some great humorous moments throughout the movie

What hasn’t aged well

It wouldn’t be a complete retro review without mentioning what doesn’t hold through to today’s standards. Surprisingly this holds up really well. The focus is on characters and trying to best each other and the boxing matches themselves are decent and good at building momentum and suspense. The one big clanker in the whole film is Gabriel openly flirting with Emily (Heather Graham). She is the younger sister of his dead friend and when I say younger….the age gap is embarrassing! Luckily the movie never fully explores this as a romantic sub plot and we’re left with just slightly creepy flirting that doesn’t blossom into anything else thankfully! There are also some racial slurs that seem over the top compared to today’s standards but only help to highlight how villainous John Gillon and his goons are.



This is a feel good movie. The on screen chemistry is on point. The villain is deliciously vile. The cons with twists and reveals are very satisfying and the boxing scenes are very well shot and add tempo bringing everything together for a very satisfying final act. There is very little wrong with this movie and I believe it’s an entertaining watch for all. You can watch Diggstown now on Amazon or Vudu (or watch it for free on YouTube)


-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-

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