Diggstown (1992)

In the gritty boxing drama *Diggstown* (1992), Gabriel Caine, fresh out of prison, orchestrates a high-stakes wager with a powerful businessman who controls the boxing-obsessed town of Diggstown. The bet hinges on Caine finding a single boxer capable of defeating ten Diggstown fighters within a gruelling 24-hour period. Caine's chosen champion is the legendary "Honey" Roy Palmer, a formidable fighter now nearing fifty, whose age raises doubts among the skeptical locals and even some of his allies. This film earns its place on a list of the best Michael Ritchie movies due to its quintessential Ritchie themes. Ritchie consistently explored the underdog narrative, the clash of ideals against entrenched systems, and the inherent drama within competitive arenas. *Diggstown* perfectly embodies these sensibilities, showcasing a flawed but determined protagonist fighting against overwhelming odds and a corrupt establishment. The film's focus on the strategic maneuvering, the moral complexities of the characters, and the raw, human drama at its core are all hallmarks of Ritchie's directorial style, making it a standout in his filmography.