The Jackpot Generation

Matt Schellhas
9 min readApr 17, 2024
Colored Sketch thanks to Copilot

It is September 4th, 1998.

Fresh off of the explosive success of Good Will Hunting, Matt Damon appears in his next film: Rounders. This time, instead of a mathematical genius who struggles to escape a rough neighborhood, Damon plays a poker genius who escaped that rough neighborhood but can’t help be brought back down by a scummy friend (Ed Norton) and the prospect of being a mediocre lawyer for the rest of his life.

It’s an okay film. $23 million domestic on a $12 million budget. 3 out of 4 stars from Ebert. 64% Rotten Tomatoes. John Malkovich doing one of the worst Russian accents ever recorded. Depending on your tastes and how you evaluate cameos and voice acting, it’s somewhere between Damon’s 10th and 20th best film. It’s decidedly okay.

But Rounders is noteworthy because it was an inflection point in America’s relationship with gambling. It introduced the public to Texas hold ’em. Not some bullshit game that only James Bond knows. Not some rigged game like blackjack. It might’ve been fancy poker, but it was still the same game that every American kid knew how to play. And no less an authority than Matt Fucking Damon was here to explain how Texas hold ’em was a game of skill, not luck. Barely gambling at all!

Combined with Swingers before it and Ocean’s Eleven after it, Rounders helped complete the Disney-ification of…

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