Blackjack with Matthew McConaughey

By Simon Willis

Matthew McConaughey slides $1,000 in chips onto the blue baize of the blackjack table. The dealer lays down a five and an eight. In blackjack the aim is to get as close as possible to 21 – with 13 there’s really no option but to “hit” and take another card. “I don’t need the eight,” McConaughey tells the dealer in his syrupy Texan drawl. “A seven will do just fine.”

She gives him a nine. “Gosh dang it!” he cries as she sweeps his money away. “McConaughey’s down a grand over here.”

The dealer hands me an ace followed by a jack. I have 21 and I haven’t even done anything. “Boom, boom! You are cashin’ in,” McConaughey says.

“Beginner’s luck,” I reply.

“Well ride beginner’s luck, man. It’s a real thaaang.”

The money, however, is not: we are playing in a virtual casino with fake dollars while we talk over Zoom from two different sides of the world. McConaughey is at home in Austin, Texas, where he has spent the pandemic hunkering down with his wife, who is a Brazilian model, and three children. We are not exactly dressed for a casino, either: he is wearing a cobalt-blue shirt and perspex-framed glasses; his hair, uncut for months, is tied back in a man-bun.

“Well ride beginner’s luck, man. It’s a real thaaang”

McConaughey watches the screen with slack-jawed concentration as he keeps track of his cards. Though I’m a novice, he has gambled for years. He doesn’t bet large sums – just enough, as he writes in his colourful new memoir “Greenlights”, to give him a “buzz”. He learnt blackjack from his older brothers, Rooster and Pat. When he received his first big Hollywood pay cheque, $48,500 for ten weeks’ work on a baseball movie called “Angels in the Outfield” in 1994, he celebrated with Pat in Las Vegas. Sitting at the blackjack table in his lucky leather jacket he played for 11 hours straight and left $2,000 up.

The gambler in him has shown up in the characters he has played as well as in real life. For most of the early 2000s, McConaughey was pigeon-holed as rom-com eye-candy with a gleaming smile and abs like railway sleepers. David Thomson, a film critic, wrote that he had never bothered to learn how to spell “McConaughey”: the actor’s formulaic movies, such as “Ghosts of Girlfriends Past” and “The Wedding Planner”, were beneath his notice.

Then, in a dramatic change of fortune, McConaughey reinvented himself in a succession of roles as fast-talking hustlers playing for high stakes. He had an electrifying cameo in “The Wolf of Wall Street” in 2013 as a stockbroker who subsists on a diet of cocaine, hookers and lunchtime martinis. In “Dallas Buyers Club”, for which he won an Oscar for best actor, he was Ron Woodroof, a rodeo redneck who makes a quick buck dealing experimental remedies to his fellow AIDS sufferers. And in 2016, in “Gold”, he played a fat, balding miner who sinks everything into a treasure hunt in Indonesia in the belief that “the last card you turn over is the only one that matters”. The critics who once dismissed McConaughey couldn’t get enough.

In the virtual casino, McConaughey explains his strategy. “I like to get a jive goin’ with the dealer,” he says as the next round begins, “get it goin’, get it goin’, see if they’re dealin’ hot!” Our computer-generated dealer was not the jivin’ type: her stiff cartoon body was visible only from the shoulders down, and she worked with silent efficiency. This didn’t stop McConaughey ladling on the charm in a performance worthy of one of his on-screen hucksters. “What you got, lady? Move your hand! If you don’t mind showin’ it I’d love to see it, and I’ll be tippin’ you when I win, ma’am.”

Hustling is in McConaughey’s blood. He was born in Uvalde, Texas, in 1969 to a family whose ancestors include cattle thieves, gamblers and a bodyguard for Al Capone. His mother, who once harboured acting ambitions herself, sold a skin lotion called Oil of Mink door-to-door. At the age of 12 McConaughey won a poetry contest after she encouraged him to plagiarise. “Shit, they’ll probably never find out,” she said, “and if they do all they can do is blame you and take your medal back, so fuck ’em.”

His father worked in the oil business, buying, selling (and sometimes stealing) piping. In his spare time he indulged in all manner of dodgy deals. McConaughey remembers driving with his dad to a car park behind a strip mall in Houston to meet a man called Chicago John. His dad handed over a wad of cash for an old watch in a shoebox. “He goes, ‘Look at that, son. A $17,000 titanium Rolex, and I just got it for three grand!’ It wasn’t a titanium Rolex and it wasn’t worth 17 grand. It wasn’t even worth 500 bucks. But that didn’t matter. It was havin’ a story to tell.”

“I like to get a jive goin’ with the dealer. Get it goin’, get it goin’, see if they’re dealin’ hot!”

This joy in telling good yarns proved to be hereditary. “My family are all good bullshitters,” McConaughey says with a smirk. Rooster, the oldest son, followed his dad into the oil trade, made his first million at 30, and flew to Vegas every fortnight to play craps. He was such a profligate gambler that the Aladdin, a hotel and casino on the strip, once offered him a suite to live in free.

These days McConaughey isn’t much of a Vegas guy. He prefers the riverboat casinos in Louisiana, where some years ago he struck it lucky playing Caribbean Stud, a variant of poker. After losing all night long, he was dealt a two, three, four, five and six of hearts. “A straight flush, didn’t even have to draw a card. All of a sudden the bells were going off – Dingdingdingding! – and I had $13,900 in my shirt pocket.”

The memory keeps him optimistic as the cards continue to go against him. With 17 in his hand, McConaughey decides to see if our dealer can do better. “Ooooh, I’m gonna let her bust,” he says. “Bye byeeeee!” She gets to 12, then 13, then 16. Blackjack has one rule that occasionally favours the player: the dealer has to keep drawing until they hit 17. If she took anything more than a five here, McConaughey would reclaim some of his losses.

She gets a two.

“She drew it!” he shrieks in disbelief. “Nice draw, lady. Man, she’s hot right now.”

McConaughey’s book is a slick retelling of his life story, rich in incident and anecdote. Its narrative is interspersed with a series of hokey, cod-philosophical life lessons derived from his experiences. Appetite for risk is a recurring theme. “More often than we care to admit”, he writes, “we don’t get what we want because we quit early or we didn’t take the necessary risk to get it.”

For a long time McConaughey’s life supported this self-image. As a young actor he spent years criss-crossing America in an Airstream trailer he called “The Canoe”, roaming wherever chance or desire took him. The macho achievements he lists in his book include doing peyote in a cage with a mountain lion.

Gambling fits neatly into this picture, and in some ways the successes of his early career seem like bets paying off. There was the time in 1992 when, having never acted before, he approached a casting director in a hotel bar. Over vodka tonics and a joint he hustled his way into a part in “Dazed and Confused”, a film about a group of high-school stoners that is now a cult classic. Four years later he was called into a meeting with Joel Schumacher, a director, to discuss a supporting part in a courtroom drama, “A Time to Kill”. He convinced Schumacher to let him play the lead instead. It was the role that made him famous.

“All of a sudden the bells were going off – Dingdingdingding! – and I had $13,900 in my shirt pocket”

In reality, McConaughey’s attitude to risk has been more prudent than he might admit. As a gambler he’s long had a habit of pocketing a portion of his winnings before he bets again, “so I don’t get too cocky and push a whole bunch out there”. And as an actor he has worked hard to limit his potential losses. Before he got the lead in “A Time to Kill” in 1996 he already had a contract to make three movies for the studio. He was out on a limb, but didn’t have far to fall.

The so-called McConnaissance, when he abandoned his life as a rom-com heartthrob, is another case in point. Around 2010 he decided that if he couldn’t get more challenging work then he wouldn’t act at all. He didn’t make a film for almost two years, a period he describes as “wobbly…I reached into my soul about it, I prayed on it.” Listening to this earnest account you’d be forgiven for thinking the stakes were high. But you have to be pretty rich to turn down $14.5m to make another rom-com and wait until your luck turns.

In a sense, McConaughey was looking for characters who represented a more extreme version of himself: “People whose choices were really gonna cost them.” This was what attracted him to playing Ron Woodroof in “Dallas Buyers Club”, a script he bought during his rom-com run but couldn’t get made. “Nobody was interested in directing it with Matthew McConaughey in the lead,” he says. Despite pressure to sell it, he held on. “It was one of those scripts where I was like, I’ll fight you for it. They would always laugh, and I would say, ‘No I’m serious. You think you can have it? See if you can whup me’.”

Eventually directors warmed to his fighting spirit and began to cast him in roles that allowed him to rediscover the scrappy underdogs he had grown up around. Kenny Wells, the fortune-hunter in “Gold”, was an impression of his father, who had himself invested heavily in a diamond mine in Ecuador. “There were no diamonds,” McConaughey says, “but it was the allure of the possible, like, ‘Oooh, what if I hit a lick?’” Woodroof was the darkest expression of this irrepressible will. With his body wasted by AIDS, long before there was any treatment for the disease, he was living on his wits. “He was doing all he could to survive,” McConaughey says. “By hook or by crook he had hustled his way to live as he did. I read it once and I said, ‘I see this.’”

Back at the blackjack table, McConaughey is hitting a lick of his own. He gets an ace and a queen followed by an ace and king: two blackjacks in a row. “I like playin’ with this lady right now,” he says.

There is time for one last hand. “Woop woop woop, come at me again! Do you lu’uv me?” The dealer lays down a jack and eight for me, and a jack and queen for him. “Eighteen and 20,” he says. “You’re good, you should stick, and I’m gonna stick too.” Finally the dealer reveals her cards: 18.

You draw, and I win!” he says, grinning widely to display a gleaming set of Hollywood teeth. “That buys us dinner tonight.”■

ILLUSTRATIONS: LUIS GRAÑENA