Honey Roy Palmer vs. Hammerhead Hagan, 'Diggstown' (1992)
Michael Ritchie's 1992 gem features James Woods' con artist challenging Bruce Dern's small-town boxing-scene king to a $100,000 bet: An aging brawler named Honey Roy Palmer (Louis Gossett, Jr.), can beat 10 boxers over a 24-hour period. And in the ninth fight, our winded hero faces Hammerhead Hagan (Willie Green), the only fighter to ever beat him in his professional career. The odds are poor for the AARP-aged brawler, and he's beaten so viciously in the early rounds that even his gambling patron pleads with him to stay down. But you know what happens when you beg this man to throw in the towel? He'll catch it on the fly and hurls it back at you — a triumph second only to the glorious comeuppance in the tenth and final match.
Pretend boxing skills: There are "aging brawlers" and then there's Gossett, who was in his mid-50s when Diggstown was shot. He looks incredible for his age — and at a muscular 6'4", still plenty imposing — but the film kindly requests some suspension of disbelief. 8
Style: Ritchie channeled some of his old Seventies magic (see The Candidate, Smile, The Bad News Bears), but his talent is more for comedy than choreography. The story elevates this bout more than the meat-and-potatoes filming of it. 6
Stakes: $100,000 plus side bets are on the line. We've seen the best from two ace hustlers and a indefatigable veteran. For Palmer to go out in anything less than a blaze of glory would be unthinkable. 10
Overall rating: 8