Best Sports Betting Movie Scenes: The Long Con Begins in ‘Diggstown’

By Brett Smiley | Published: July 3, 2018 at 12:00 pm

As a change of pace from sports betting legislation and the US gambling legislation beat, and because we’re about sports betting culture, too, Sports Handle continues the a 15-part series on The Best Sports Betting Scenes in Television and Movies.

(Also, it’s the day before the Fourth of July and most of you are unplugged or loading up on beer and hot dogs.)

There’s a lot of high-quality movies centered on gambling, including on horse racing and poker (Let It Ride and Rounders). All quality gambling scenes, whether strictly sports betting or not, the focus of the film or a short aside, will be included/considered.

Best Sports Betting Movie Quotes and Scenes: Caine (James Woods) Begins to Set Up Gillon (Bruce Dern) In Star-Studded Boxing and Sports Betting Comedy ‘Diggstown’.

In this scene from the 1992 sports (betting) comedy ‘Diggstown,’ ex-convict Gabriel Caine (James Woods) begins to lay the groundwork for a scheme to empty the pockets and bank account of Georgia gambler and prominent city figure John Gillon (Bruce Dern). Caine challenges Gillon’s sports betting acumen and the sport that defines Diggstown: boxing.

“But would you bet 2,000 bucks on it?” Caine says incredulously of the match before the men.

“Are you joking?” Gillon replies. “There’s two things we never joke about in Diggstown, Mr. Caine: Our boxing and our betting.”

Later, the (silly) premise shapes up when Gillon’s co-conspirator Fitz (Oliver Platt) bets Gillon $100,000 that no one man can defeat ten Diggstown boxers in one day. The scene below mixes in Fitz’s pool hall hustling (he eventually wins the car). Enjoy. (It’s not on Netflix right now, unfortunately.)

[Also see: Best Sports Betting Scenes: In ‘Bronx Tale,’ ‘We Can’t Win, Mush Bet Kryptonite’]

If you have a suggestions for a great sports betting/gambling scene in movies or television, please send it to [email protected] or Tweet us at @sports_handle. If it’s not already on the rundown, we’ll be happy to give a shoutout. All suggestions appreciated.