There’s an irrefutable charm that radiates from the film Rounders. Premiering on September 11, 1998, John Dahl’s stylish peek into the disreputable world of high-stakes poker oozes charisma. It possesses a rakish secret-handshake saunter that makes you ever so briefly consider giving up the dependable comforts of the nine-to-five and dive head-first into the seedy underbelly of the unknown. But you don’t. Even though screenwriters David Levien and Brian Koppelman (who would go on to co-create Showtime’s Billions) make the clandestine world inhabited by Matt Damon’s Mike McDermott appear to be just the right balance of exciting and dangerous, we understand that the reality is less glossy than its cinematic proxy. As someone who’s spent more time at an Atlantic City $1/$2 no-limit hold ’em table than he cares to admit, I can confirm that poker is hours upon hours of boredom broken up by brief moments of ecstasy.

Also, the poker room smell is not super great.

Rounders is the greatest gambling movie ever made. Perhaps you prefer more classic fare like The Sting, The Hustler, or The Cincinnati Kid. Maybe The Color of Money or modern favorite Mississippi Grind is more your style. Awesome. I love those films too. But to a certain subset of lovable degenerates, Rounders was a game-changer. It introduced the world to the seductive highs and debilitating lows of the maddeningly fickle yet undeniably alluring siren of no-limit Texas hold ’em. If you’re reading this, the mere existence of Rounders has either been a financial boon or a monetary scourge.

And if you’re being honest, it’s probably the latter.

Premiering five years before the great Chris Moneymaker-led poker boom of 2003, Rounders evolved into a slick “how to guide” for the burgeoning swarm of young gamblers attempting to be the next rags-to-riches poker success story. Winning the lottery’s a pipe dream; winning the World Series of Poker is… well… a slightly more realistic pipe dream that’s way more fun.

Rounders was moderately successful at the box office. It opened at number one on its way to earning just under $23 million domestically, but its legacy and influence extend beyond the numbers. The film evolved into a cult hit and its lingo became a fixture in poker nomenclature. Rounders didn’t invent terms like “the flop,” “nut straight,” or “splash the pot,” but the movie popularized them. Suddenly, phrases like “lays down a fucking monster” were being bandied about college campuses while squares like me hid their meager poker winnings in an old VHS of Scream 2 and a dogeared copy of Doyle Brunson’s “Super System.”

Yes, Rounders as a movie is terrific. It’s one of Matt Damon’s best roles; Edward Norton is pure magic; John Malkovich’s Teddy KGB is an all-timer; and the closing credits highlight the most underrated Counting Crows song this side of “Omaha.” But after 20 years, it’s the film’s cultural legacy that endures.

Listen, I get it. Nobody cares when someone brags about liking The Strokes before “Last Nite” was cool, but THAT SAID, I became obsessed with Rounders in 2000. As a senior in high school, my friends and I wore out my VHS copy (thanks, Columbia House!). I say this not to brag — well, I say this not only to brag — but to illustrate how popular this film became during the 2003 poker boom. Thanks to the influence of Rounders, my friends and I played a Gladwellian amount of Texas hold ’em from 2000-2003. After Moneymaker became an overnight millionaire, a surge of young people flocked to both poker and Rounders. Having already suffered through the inevitable poker growing pains, I was there to assist with their transition… for a nominal fee of all their money.

Spring break used to be dominated by the Panama Cities of the world, but Rounders helped usher in the era of friend-trips to Las Vegas, Atlantic City, or if you weren’t 21, Canada. If Moneymaker was the spark, Rounders was the gasoline that helped ignite the great poker inferno of the mid-aughts. The poker craze wouldn’t have been as potent without relatable characters like Mike McDermott and Chris Moneymaker. The real World Series of Poker and fictional world of Rounders worked together to forever alter the perception of the sport. The unsavory stigma had been broken. And if you happened to encounter someone who had yet to fall under poker’s hypnotic trance, Rounders provided the necessary rhetoric you’d need to escape any conversational jam.

“Why do you think the same five guys make it to the final table of the World Series of Poker EVERY YEAR? What, are they the luckiest guys in Las Vegas? It’s a skill game, mom/significant lover/well-meaning loved one!”

Thanks to Rounders, poker evolved from a social taboo into an acceptable form of entertainment. The sport is no longer as popular as it was during its 2003 boom, but that’s okay. If and when a new version of Moneymaker emerges, Rounders will be there, waiting to inspire a whole new generation of poker players.

Where to stream Rounders