Diggstown (1992)

Synopsis
In this comedy, a charming con man teams up with a boxer fallen on hard times in hopes of making some quick money. After doing time for selling art that turned out to be forged, Gabriel Caine (James Woods) and his partner Fitz (Oliver Platt) set their sights on a village called Diggstown; Fitz arrives first and takes several well-heeled locals in a high-stakes poker game, and then Gabriel follows to make a sporting proposition to John Gillon (Bruce Dern), the city's wealthiest citizen. Gabriel tells Gillon he has a boxer that can beat any ten opponents Gillon can line up, in the same day. Gillon takes the challenge and places a big enough wager to make matters even more interesting, but now Gabriel has to convince Honey Ray Palmer (Louis Gossett Jr.), a middle-aged former boxer who has been taken for a ride by Gabriel in the past, to go along with this scheme. In the meantime, Gabriel works out a deal with gangster Victor Corsini (Orestes Matacena) to back his bets while romancing Emily (Heather Graham), the sister of a large and ill-tempered fighter Gabriel met while behind bars. ~ Mark Deming, All Movie Guide