A Gambling-Related Pop Culture Summer Survival Guide

Written By Steve Friess on May 30, 2023 - Last Updated on June 26, 2023
State of Play Summer Gambling Recommendations

Ahh, summer! Finally here (unofficially, per odd American tradition). Time to chill out, go outside, catch up. And time for me to have an excuse to offer a gambling and Las Vegas-adjacent multimedia panoply of recommendations I’ve been hoarding.

“The Big Break: The Gamblers, Party Animals, and True Believers Trying to Win in Washington While America Loses Its Minds” by Ben Terris: I admit I haven’t read this yet – it’s out on June 6 – but I read the excerpt in the Washington Post about political bettor Sean McElwee and can’t wait for more. Terris is a tremendously gifted WaPo features writer who gets himself inside some of the coolest suites of D.C. power, like up-and-coming progressive strategist McElwee’s poker game. But it’s his extensive accounting of McElwee’s boastful wagering on politics and the role it played in undoing his rising influence in Democratic circles. This passage alone sold me:

Sean was not shy about his gambling. He told people he bet $20,000 on Biden’s 2020 presidential campaign. He’d make prop bets with his buddies around the poker table. He’d sometimes end conference calls with other organizations by seeing if anyone wanted to make a wager with him about upcoming elections. He put tens of thousands of dollars a year on prediction markets, sometimes on contests as far‐flung as the Seattle mayoral race (“I won like $6,000 on that,” he told me). He once told me he would sometimes commission little polls “mostly” for the purpose of getting intel that he could use to make smart bets.

The Star-Spangled Gamblers Podcast: Along the same lines, if you’re bored with the typical podcasts about sports betting, check out the weekly-ish conversations about wagering on politics from this crew. Helmed by Pratik Chougule, a Yale Law graduate and longtime foreign policy researcher and writer. Come for the predictable stuff – the 2024 GOP presidential primary, the number of seats Democrats were going to win in the 2022 elections – but stay for fascinating discussions of international politics from a wagering perspective and wild side bets on, say, the odds of Russia nuking Ukraine by the end of June.

Look for the cameos by poker stars

“Lucky You:” This Eric Bana-Drew Barrymore rom-com box office bomb from 2007 popped up on HBO Max (now Max) a while ago at a moment I needed something to hate-watch. Instead, I ignored the predictable treacle that is any film in which Barrymore is a winsome but wise ingenue and found something surprising, a rare film that accurately captured the act of gambling in a certain era Vegas that I miss. Bana plays a handsome (and clearly compulsive) young poker player with daddy issues, his daddy being a two-time WSOP champ played by Robert Duvall. All of that is Hollywood nonsense right down to the climax at (of course) the WSOP Final Table, but what the film gets more correct than most is the actual grind and fickle nature of the cards. Presumably set around 2001 when WSOP was still played at Binion’s downtown without hole cams or thousands of players, there is an emotional truth in Duvall’s grizzled old veteran talking about how the tournament was getting too big for the old guard to ever win again. Also, it’s just fun to spot the long list of cameos by poker stars (Jennifer Harmon! Doyle Brunson! Johnny Chan!) as well as bit parts from the likes of pre-Hacks Jean Smart, pre-Iron Man Robert Downey Jr., and pre-Boardwalk Empire Michael Shannon.

“The Godfather of Poker:” In the wake of Doyle Brunson’s death in mid-May, I went back to re-read his memoir. You should, too. Most poker books, including Brunson’s other ones, are about the cards themselves. Brunson’s is about a truly original American life, full of honest introspection about his life as a parent and what it cost him to become the legend he was.

“The Cooler:” Pre-Shameless William H. Macy as a guy with such awful luck that a casino hires him to kill other players’ hot streaks gives a masterclass in playing a low-life sad sack who doesn’t really know what to do with himself when his fortunes turn too. This 2001 film, another oldie that Peacock put in my path recently, has its own set of Vegas cliches, but it also has some of the most honest sex scenes on film and many laugh-out-loud moments.

Breaking down the myth about gamblers

Jeopardy! Masters: Without giving anything important away, this series now on Hulu was very much about Vegas-based sports bettor James Holzhauer, who came to fame during a 32-game winning streak in 2019 on the regular quiz show. His work in the 10-episode “Masters” further breaks down an old myth about gamblers (or just people from Vegas) as uncultured and anti-intellectual. The guy knows obscure opera, geography, and literature – and, yeah, his risky all-in wagering strategies for Daily Doubles have revolutionized a genteel game show.

Pachinko: Luscious, expensive and transportive, this award-winning eight-episode Apple TV+ series based on the book is tangentially about gambling in the sense that the business of the characters involves running salons for the Japanese game of Pachinko. It’s about a lot more than that – Japanese bigotry against Koreans, family drama, sexual politics and violence – but there is a gambling culture embedded in this story that Americans rarely glimpse. A second season is coming, too.

Five Hundy By Midnight: After 20 years of focus on Vegas and gambling that included six years creating and co-hosting “The Strip” podcast, I stepped away from the beat and stopped listening to Tim and Michelle Dressen for a while. Much to my great pleasure, the “original Las Vegas podcast” that was once a rival of ours remains fresh, fun, informative, and as fiercely independent as ever.

“Mrs. Davis:” OK, OK. This has not a damn thing to do with gambling. I just love it, it is partly set in Reno, and there is a schlocky element involving a casino magic show. Mostly, though, it is the weirdest, funniest, strangest little show I’ve seen in years and it’s free on Peacock. Mrs. Davis stars the great Betty Gilpin of Netflix’s “G.L.O.W.” as a motorcycle-riding nun on a quest to find the Holy Grail. There’s a big theme here about the indistinguishable difference between the God of organized religion and an all-knowing, all-powerful artificial intelligence persona known as Mrs. Davis, but if you don’t want to think that hard just go for the ride here.

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Steve Friess

Steve Friess writes the State of Play column for PlayUSA twice a week. He's a veteran gambling-industry reporter who began covering Las Vegas in 1996 and covered the openings of resorts in Asia, Europe, and across the U.S. His bylines have appeared in The New York Times, Playboy, New Republic, Time, BusinessWeek, Newsweek, New York magazine, and many others. He, his husband, their children and three Poms live in Ann Arbor.

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