Matt Damon

Even if Matt Damon gave up acting today and played poker in perpetuity, chances are high that he would never play a single hand of Texas Hold’em more meaningful than the one immortalized on the big screen 17 years ago.

Portraying a New York City law student by the name of “Mike McDermott” in the film Rounders, Damon made poker cool five years before Chris Moneymaker ever had the idea. In the movie’s climactic scene Mike McD – as he is better known to film buffs and poker fans alike – takes on feared Russian mob boss “Teddy KGB” in an epic heads-up match. With his bankroll, and likely his life, on the line, Mike McD manages to spot his nemesis’ tell before outplaying him for the biggest pot of his life.

While the scene was fictional of course, every poker player can no doubt recount the hand’s crucial elements: holding eight-nine of spades with Teddy KGB on the ropes, Mike McD slowplays his man to perfection after flopping the nut straight on a six-seven-ten rainbow flop. The turn and river changed nothing, prompting Teddy KGB to move all in and turn the pressure up. Mike McD calls the big bet with the nuts, redeeming both his bankroll and his sense of self-worth after a series of misadventures.

As the film concludes Mike McD sets off for Las Vegas to try his hand at the World Series of Poker – just as an entire generation of players would eventually do in 2003 after Moneymaker’s big win in the WSOP Main Event. While Rounders was not well-received by critics during its theatrical run, the poker community rightfully holds it up as the pinnacle of poker filmmaking. Much of that reputation is due in large part to Damon’s performance, as the young actor managed to capture both the exhilaration and the anguish, of playing high-stakes poker.

Matthew Paige Damon was born on October 8th, 1970 in Cambridge, Massachusetts to relatively well-off parents. They divorced when Damon was just two years old, however, and he spent much of his childhood living in a communal home for families on the lower end of the economic spectrum. During high school Damon showed a talent for theatre and drama, appearing on stage alongside his childhood friend Ben Affleck.

Damon began attending the prestigious Harvard University in 1988, but he continued to pursue acting and even landed bit roles in films like Mystic Pizza. By 1992 Damon was just one semester short of graduating with a B.A. in English, but he left school that year to take a feature role in 1993’s Geronimo: An American Legend. Operating under the belief that the film would elevate him to star status, Damon watched as the movie achieved lackluster results at the box office.

While Damon went on to attract critically positive reviews for his role in Courage Under Fire (1996), it was a film released one year later that launched his ascent into Hollywood’s upper echelon. Working in conjunction with Affleck, Damon had co-wrote a screenplay entitled Good Will Hunting during his last years attending Harvard. When the film hit theatres in 1997, with Damon portraying the lead and Affleck co-starring, both men were lauded for their work. Damon and Affleck won the Oscar for Best Original Screenplay at the 1998 Academy Awards, and Good Will Hunting earned nine Oscar nominations in total.

Damon went on to an immensely successful career in Hollywood, appearing in hit films like Ocean’s Eleven (2001), The Bourne Identity (2002), Ocean’s Twelve (2004), The Bourne Supremacy (2004), Ocean’s Thirteen (2007) and The Bourne Ultimatum (2007). In 2007 Forbes magazine ranked Damon as the “most bankable star” in Hollywood by virtue of his film’s box office performance.

While those roles were certainly meaningful, however, poker fans will always remember Damon as Mike McD. As the first film to depict poker in a realistic manner – complete with trips to shady home games, concealed attempts to cheat the game, and teams of professionals lightening the load for tourists in Atlantic City – Rounders captured the essence of what it meant to play the game. For many longtime poker players, Damon’s character was speaking directly to them when he had the following exchange with his nefarious friend “Worm”:

Worm: You know what always cheers me up?
Mike McDermott: No, what’s that?
Worm: Rolled up aces over kings. 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 McDermott: Fuck it, let’s go.
Worm: Don’t tease me.
Mike McDermott: Let’s play some fucking cards.

Damon seemed to have taken his character to heart the following year when he and co-star Edward Norton entered the $10,000 buy-in WSOP Main Event in 1998. The appearances were sponsored by the Binion’s Horseshoe in Downtown Las Vegas – the first home of the WSOP, meaning the casino paid for the actors’ entry fee – but the tournament went well enough for two rank amateurs. Damon, in particular, enjoyed a moment on the felt that seemed fitting for an actor accustomed to living out storybook endings.

In a PokerNews retrospective published in February of 2009, respected poker writer Martin Harris memorialized the Rounders stars’ remarkable run:

The actors ultimately acquitted themselves rather well despite having relatively short Day Ones. Norton’s day was the shorter of the two, lasting only a couple of hours before he was eliminated when his nines full of tens were bettered by Surindar Sunar’s quad tens. Damon, meanwhile, still had close to his starting stack when Norton was sent to the rail, and would survive for a few levels, despite being seated at the same table as Super/System author and two-time WSOP Main Event champ Doyle Brunson.
As one would expect, Damon and Brunson’s table attracted the most attention during that first day of the Main Event, with a horde of fans crowding the ropes all day in an effort to catch a glimpse of the action. Finally, Damon looked down to find himself having been dealt pocket kings on the button, and accordingly he made a big raise. Brunson, however, was waiting for him in the small blind with aces, and so promptly reraised all in. Damon made the call, and when no king came to save him he joined his co-star on the rail. ‘I sat with Doyle [and] I lost the way I would have wanted to,’ said Damon afterwards. ‘I’m going home with a story.’

Damon’s interest in poker remained relatively light after that, but during the poker boom’s peak he became involved in a series of high-stakes “Hollywood home games.” Hosted primarily by actor Tobey Maguire, the largest of these private games featured a revolving lineup of celebrities like Leonardo DiCaprio, former poker champs like 2007 WSOP Main Event winner Jamie Gold, and anonymous millionaire businessmen.

In 2014 former cocktail waitress Molly Bloom – who helped host the games between 2004 and 2010 along with Maguire – published a tell-all titled Molly’s Game: From Hollywood’s Elite to Wall Street’s Billionaire Boys Club, My High-Stakes Adventure in the World of Underground Poker. Bloom described a regular home game in which players, Damon included, routinely bought in for $50,000 and engaged in heated sessions well into the morning.
While the book lambasted Maguire as an arrogant, petty man who possibly used his friends to stage Rounders­-like games in which he always held the edge, Bloom only had nice things to say about Damon:

He was one of the nicest, most humble, down-to-earth guys I have ever met. He was just genuine. There were no airs about him.

Damon continued to play tournament poker as well, and in 2009 he was featured in ESPN’s coverage of the WSOP Main Event, along with lifelong friend and fellow gambler Affleck. Once again showing his natural knack for the dramatic, cameras happened to catch Damon play a particularly interesting pot early in the tournament.

Holding just ten-six offsuit, Damon saw a cheap flop and hit paydirt on a 10-10-6 board. Rather than press the action and get value from the monster full house, Damon checked to his opponent on all three streets, perhaps hoping for a repeat of his famous trapping of Teddy KGB. The other player didn’t bite though, and he checked back on the river, much to Damon’s chagrin.

Damon’s lone career cash in a live tournament came in 2011, when he finished in 45th place at the World Poker Finals at Foxwoods Casino, earning a $540 payday on his $250 buy-in.