Diggstown

“Do you know the difference between a hustler and a good con-man? A hustler has to get out of town as quickly as he can, but a good con-man—he doesn’t have to leave until he wants to.” —James Woods, Diggstown

“It’s better to burn out than to fade away,” as Neil Young says, and in the realm of critical perception, there’s no better example of this than director Michael Ritchie, who might have been as exalted as Hal Ashby had his career ended at the same time. From the late ’60s to the mid-’70s, Ritchie went on a tear that was nearly as impressive as American contemporaries like Francis Ford Coppola or Robert Altman: 1969’s Downhill Racer, the first of two collaborations with Robert Redford, about the tolls of being a single-minded champion; 1972’s Prime Cut, a Lee Marvin-Gene Hackman gangster movie with a sliver of dark fish-out-of-water comedy; 1972’s The Candidate, also with Redford, a brilliant political satire about the unlikely ascendency of young lawyer recruited to a Senate race he’s not supposed to win; 1975’s Smile, an Altman-esque survey of a California beauty pageant that’s just as funny and political as The Candidate; and the irreverent 1976 baseball classic The Bad News Bears, which reserved its sympathies for a profane, cantankerous coach (Walter Matthau) and his lovable band of little-league misfits. 

But Ritchie kept on making movies throughout the ’80s and ’90s, and saw his reputation diminish sharply on notorious flops like The Golden Child, The Couch Trip, Fletch Lives, and Cops And Robbersons, just to name a few. Granted, early retirement would have denied the world Fletch (and the culture of Fletch quotes), the above-average TV movie The Positively True Adventures Of The Alleged Texas Cheerleader-Murdering Mom, the promising first half of The Scout, and today’s New Cult Canon entry, the glorious 1992 con movie Diggstown, but Ritchie was rarely again seen in the same exalted light. Some of that is fair: Even hardcore auteurists would have trouble finding the green shoots in the barren comic wastelands of The Golden Child or Cops And Robbersons, and The Scout, for all its merits, is a case of a filmmaker not having the conviction to follow through on a premise he would have nailed two decades earlier. Artists don’t always bring their careers in for a soft landing, and Ritchie fell harder than most. 

Yet the Ritchie of old—relaxed, cheerfully rebellious, a friend to underdogs and scalawags—is all over Diggstown, which could have been made the day after The Bad News Bears without anyone being the wiser. As a rascally con-man running a high-stakes boxing hustle, James Woods joins the pantheon of Ritchie heroes like Redford in The Candidate, Matthau in The Bad News Bears, and even Chevy Chase in Fletch—all charismatic outsiders who are playing a dirty game against the establishment. They’re all cheating to win, but we root for them anyway, because everyone else is cheating, too, and in much more diabolical ways. Endings don’t get more crowd-pleasing than the one in Diggstown—though it never got much of a crowd to please—but what we’ve just witnessed isn’t a Rocky-like triumph in the ring, but one con artist outsmarting another, which is utterly and gloriously ignoble. 

All exuberant smiles and greasy charm, Woods is ideally cast as Gabriel Caine, a newly sprung felon who immediately heads into his next big scam the minute he walks out of a Georgia prison. Caine and his partner Fitz (Oliver Platt, also excellent) head over to nearby Diggstown, a dingy hicksville renowned for its boxing scene. Also sporting an exuberant smile— albeit with a malevolent twinkle in his eye—Bruce Dern plays John Gillon, a former boxing manager who has a piece of every business in town. Matching wits with a slickster like Gillon isn’t a wise play, especially on his home turf, but Caine can’t help himself. With cash fronted by gangsters who almost want him to fail, just so they can have the pleasure of killing him, Caine makes Gillon a bet: $100,000 that his buddy, “Honey” Roy Palmer (Louis Gossett, Jr.), a 48-year-old former boxer turned YMCA instructor, can defeat 10 Diggstown boxers in one 24-hour period. 

This would be the part in an average sports movie where we watch Palmer montage his brittle bones back to their old density and then nobly take on all comers, in an extraordinary triumph of athleticism and steely determination. And while there’s some of that—enough to make it clear that victory isn’t entirely rigged—Diggstown is more about the games of the mind than the body, as Caine and Gillon set to work on tweaking the odds in their favor. Caine lays down bribes to a pair of sibling pugilists to throw their fights (which one of them does with tragic incompetence); Gillon plants ringers by stretching the boundaries of Diggstown residency. In this delicious pre-fight speech, Gillon devises a group strategy to wear Palmer down:

“Dear Lord, please give us the strength and courage to tear this man from limb to limb.” If there’s one line that embodies the spirit of Diggstown, it’s that one: A locker room prayer that seethes with wicked intent, a rebuke to the stirring “Win one for the Gipper” speeches that preface the movie moments before the gladiators enter the arena. It’s possible that greed motivates Caine and Gillon to a certain extent, but not nearly as much as the art of the con. They’re competing for who can get one over on the other, and it means so much to them that Gillon is willing to stake his livelihood and Caine is willing to stake his life. There’s an innate likeability to Caine that puts us in his corner—Woods’ ingratiating, motor-mouthed charm has never been better exploited—but the real difference between them is power. Gillon has it, Caine doesn’t, and who wants to root for the bully?

Diggstown isn’t without its share of missteps: The wind-up takes a bit too long, clogged up by subplots—one involving the sister (Heather Graham) of Caine’s former prison buddy, the other about Charles Macon Diggs, the haunted legend who gives Diggstown its name—that exist mainly to play up Gillon’s villainy. And one turn concerning the bribed siblings goes to such a dark place, especially in the context of the Deep South, that it throws the tone off-balance. But Diggstown still devotes about half its running time to fight night and each bout has its own flavor, as Caine and Gillon move their chess pieces around the board. Palmer, the irascible veteran, seems to be having a good time running his part of the con, which in the case of the ol’ “brown bottle” trick, calls on him to work the midsection like a squeeze doll: 

Diggstown closes with one of the most satisfying twists I can recall—one I won’t spoil here—and it’s earned by both Palmer’s familiar sports-movie feats of will and the tactics of two con-men wh   o keep pulling aces from their sleeves. There are echoes of Ritchie’s The Bad News Bears in the ending, which doesn’t celebrate sporting triumph so much as the heroic snottiness of the underdog. In talking about his great 1953 film Pickup On South Street, director Sam Fuller said that a pickpocket was more of an artist than a criminal, and that gets at the reason why we watch con movies like Diggstown. Thieves and cheats are the bane of society, but when they can do it with panache, that’s a whole different story. 

Coming Up:
December 29: The Cook, The Thief, His Wife And Her Lover
January 19: Dazed And Confused
February 9: Observe And Report