Gabriel Caine (James Woods) is getting out of prison soon; he's a conman who has not given up his schemes while inside, in fact while there he has helped five men to escape, and the warden (Marshall Bell) is all too aware that he has, only he cannot prove Caine's involvement. His associate, Fitz (Oliver Platt), meets him during visiting hours to discuss their latest scam to do with the nearby Diggstown, whose citizens are obsessed with boxing - the place is named after the boxer who they were most proud of until he suffered a terrible defeat which confined him to a wheelchair. So what does Caine have in mind?
Diggstown was known as Midnight Sting in the United Kingdom, a blatant allusion to a certain other conmen movie which earned itself semi-classic status down the years, but this little item conspicuously failed to carry off the same feat. What it did win was cult status, which was all very well but back in 1992 everyone involved clearly thought they had a crowdpleasing blockbuster on their hands so when it scraped back only about four million dollars it's safe to say there was a lot of disappointment for the filmmakers. What seems to have landed most of the blame was the advertising campaign which put people off seeing it instead of the other way around.
Whether that was true or not, or whether the public just weren't keen on watching a boxing movie in '92 no matter how it was advertised, isn't clear, but what was apparent is that it didn't deserve to flop, because it may have played out an implausible premise but it did so in an undeniably enjoyable fashion. What can you say to a movie which presents James Woods as a fast-talking conman, the sort of role he was born to play and awarded a wealth of funny lines here? Not only that, but Oliver Platt was ideal in much the same vein, and the boxer they choose, Honey Roy Palmer, was played by Louis Gossett Jr in a manner that meant he and Woods should really have been teamed up for other double acts.
It was not to be, because of the aforementioned failure at the box office, but if you appreciated stories where shady characters pulled a fast one on one another with considerable style in a plot filled with action, drama and laughs then you really couldn't turn this one down. Woods' Caine is a hero since he could have used his powers selfishly, but during the course of the narrative he applies them for good thanks to the man who corruptly ensured he owns the region having fixed the final Diggs fight so that he couldn't win, thereby guaranteeing he would make a fortune on the bets of the locals. And that man is? Boo-hiss baddie John Gillon, played with a splendid loathesomeness by Bruce Dern in a cast where director Michael Ritchie reminded us of the great character work of his seventies heyday.
The bet Caine makes with Gillon is that his man Palmer can beat ten bouts of ten different fighters - that's right, we're supposed to believe that Palmer is such a fantastic boxer, even in middle age, that he can survive something like twenty-five rounds and knock out each and every one of those rivals. It's a long shot even without the movie magic to gee it along, and the script, based on the Leonard Wise novel, was careful not to have us too convinced one way or the other about whether Palmer can truly achieve this goal. Meanwhile Gillon adds threats and even murder to the complexities of the wager, making it clear he's not going down without a fight either. Also appearing was Heather Graham as the daughter of one of Caine's prison buddies, helping reveal the extent of the villainy they are up against, and you could argue they made Gillon such an evil character that became implausible as well, but it was all part of an entertainment which supplied seasoned Hollywood qualities to a time where the cool movies were moving away from them. Music by James Newton Howard.
American director, from television, whose films of the 1970s showed an interesting, sardonic take on America. After sour skiing drama Downhill Racer, he had an unhappy experience on the bizarre Prime Cut before a run of acclaimed movies: political satire The Candidate, the excellent Smile, coarse comedy The Bad News Bears, and another sporting comedy Semi-Tough.