
Damon, who attended Harvard, had a knack for portraying salt-of-the-earth geniuses. But it would be remiss not to note that while both “Good Will Hunting” and “Rounders” are hidden-genius Hero’s Journey tales, “Rounders” is also a glorification of what is essentially a gambling addict’s relapse.
I mean, think about it. You’re in law school, then you exhibit a whole movie’s worth of addiction behavior, then you quit law school, and you leave town with the following quote: “First prize at the World Series of Poker is a million bucks. Does it have my name on it? I don’t know. But I’m gonna find out.”
More History
Damon’s co-star Edward Norton was a hot commodity, having been nominated in 1996 for his film debut, “Primal Fear.” Gretchen Mol (who plays Damon’s character’s love interest) was hot too; she'd just graced the cover of Vanity Fair, which queried, “Is she Hollywood’s next ‘It’ Girl?”The street-smart, seamy backroom milieu of “Rounders” was rife with 1970s sports references: “Worm and I fell into our old routine like Clyde Frazier and Earl The Pearl Monroe,” “You look like Duane Bobick after a round with Norton,” and “To celebrate Mike’s Ali-like return to the ring, I’ll sit with y’all for a while.” It also sported a gritty backup cast of character actors like John Turturro and Michael Rispoli (later of “The Sopranos”) who could make such lines ring with street-cred authority.

Though “Rounders” topped the box office on its opening weekend with $8.5 million, it ended up making $22.9 million, compared to the $225.9 million by “Good Will Hunting.” But like the proverbial cream rising to the top, “Rounders” has quietly become somewhat of a classic.
The Story
The movie kicks off with Mike McDermott (Damon) gambling in the illegal underground poker club of Russian mafioso Teddy KGB (Malkovich), blowing his entire savings, and then swearing off gambling for good (yeah right).
Mike had been funding his law school studies with gambling earnings. To continue studying, he takes a part-time truck delivery job offered by his gambling partner and friend Joey Knish (Turturro). Mike goes straight for a time, trying to live a peaceful life with his girlfriend and fellow law student Jo (Mol).
Then, Mike’s childhood buddy, Lester “Worm” Murphy (Norton), gets out of prison. Worm’s still carrying major debt he incurred before going to jail. Grama (Rispoli), Worm’s former enforcer, has consolidated Worm’s debt, which is continuing to accrue juice (interest). Grama gives Worm five days to pay it all back.
One of the hilarious running gags of the movie is Worm’s perennially jovial (but entirely untrustworthy) knowing smirk, intuitive understanding of addiction psychology, and devil-on-the-shoulder uncanny timing for when to say the perfect thing to cause an instantaneous collapse of Mike’s (pun intended) fragile house of cards no-gambling resolve.

Worm: “You know what always cheers me up when I’m feeling [low]?
Mike: “What’s that?”
Worm: “Rolled up aces over kings!”
Mike: “That right...?”
Worm: ”Yeah, check-raising stupid tourists, and taking huge pots off of them. Playing all-night high-limit Hold‘em at the Taj … ‘where the sand turns to gold.’ Stacks, and towers of checks I can’t even see over ...”
Mike: “Let’s go.”
Worm: “Don’t tease me...”
Mike: “Let’s play some (...) cards.”
Worm: fist pump (as J. Geils Band’s “Funk 49” kicks in on the soundtrack).
Mike jumps back in the game to help Worm clear his debt, which naturally results in his eventually losing interest in legal studies. Jo is not happy and, heeding Mike’s best advice to her, dumps him. “I learned it from you Mike. You always told me this was the rule. Rule number one: Throw away your cards the moment you know they can’t win.”

Eventually Worm goes too far, talking Mike into cheating in an upstate New York game with off-duty cops; and they end up getting caught, stomped, thrown out on their ears, and losing their entire roll. Mike finally recognizes Worm for the incorrigible, parasitic ne'er-do-well he is, and leaves him to find his own way home after Worm reveals his debt is ultimately owed to the very dangerous Teddy KGB.

Succumbing to Addiction Versus the Hero’s Journey
Finding one’s true calling can sometimes become a form of addiction, depending on the profession. Ask any battle-hardened Navy fighter pilot. Or NFL player. Or pro boxer. But the honoring of one’s talents is a tricky thing.For Mike McDermott, it’s clearly going to be a life-long struggle, considering that he opens the movie with the voice-over monologue: “Listen, here’s the thing. If you can’t spot the sucker in your first half hour at the table—then YOU are the sucker. Guys around here will tell ya, you play for a living. It’s like any other job. You don’t gamble, you grind it out.”
All in All
The belated success of “Rounders” was due to its feeling hyper-real, like it was written by experts who had lived those 36-straight-hour games in those smoky card caves and felt their souls ricochet from ice-cold fear to the crack-high elation of winning huge piles of money-for-nothing.