For day 4 of 5-Word’s Sports Movie Week, we’re going boxing.
All six Rockys in one.
Gabriel Caine, a conman just released from prison, heads straight to the small town of Diggstown to run his next – and biggest – scam. He’s going to take down John Gillon, the man who owns most of the town, by betting on Caine’s own fighter against ten local men. Ten fights in one day. With the whole town at stake.
I can’t remember if I’ve mentioned this before (and I can’t be bothered reading through more than 270 reviews in order to check) but a couple of years ago, the esteemed Empire magazine ran an online feature about what they called “The 27%ers”; actors whose mere presence alone automatically increased the quality of a film by – oddly enough – 27%. Four actors who obviously belong in that category are James Woods, Oliver Platt, Louis Gossett, Jr. and Bruce Dern. Wouldn’t you know it, but all four of them happen to star in this flick from director Michael Ritchie, the man behind Fletch and The Bad News Bears. Does that mean it is 108% better than it would have been without them? I’d say that is one of the great philosophical questions of our time.
Known in the US as Diggstown (which isn’t really the most helpful title in the world), the flick is set in one of those small towns made famous by any number of A-Team episodes. The type of town where one corrupt old geezer owns everything and everybody and has all the local hard men in his pocket for when things get rowdy, including a young Jim Caviezel.

It’s the lack of socks that really makes the whole outfit sing, isn’t it? Man, sometimes I miss the nineties.
John Gillon, played by the fantastically weaselly Bruce Dern, is the geezer here. James Woods is Caine, the sharpest grifter around. The two of them make a great match, frankly. Gillon is sharp enough to know from the word go that Caine is playing a con, but his ego makes him continue with the fight, confident that he can outwit Caine and that his boys can outpunch Caine’s fighter “Honey” Roy Palmer, played by Louis Gossett, Jr. Caine’s quick wit and big mouth get him into (and mostly out of) almost as many scraps as Palmer. Gossett and Woods have such an easy chemistry together; the type buddy movies are made from.
Midnight Sting is billed as a comedy, but in the same way something like Midnight Run is a comedy. The laughs don’t come from gags, but from the genuine interplay between the characters brought out by an excellent cast. Steven McKay’s script has just as many dramatic as comedic moments though, not to mention the odd unexpected, and somewhat unlikely, twist.
As a filmmaker, Michael Ritchie isn’t about visual tics or tricks, he’s about actors and storytelling. That’s where this film works. The script skirts dangerously close to cliche and predictability, but the performances raise the quality to something that is a pleasure to watch. And yes, there is a musical training montage. What boxing flick would be complete without one?
James Woods as a conman… that’s gotta be something to see!
It’s been ages since I seen this man but I remember it being really good. A very underrated little flick