Hollywood Gambles On A Big, Wild Bunch Of Movies And Shows

You don’t need me to tell you gambling has exploded in recent years.

And you know who else has noticed? Hollywood, as evidenced by the sheer number of gambling-centric movies and shows in the pipeline.

So I thought it would be fun to take a quick peek at them and give a best- and worst-case scenario for each. Basically, I’m going to review them before they are released. What could go wrong?

Starting with the project I’m personally most excited about …

Advantage Player

HBO announced this series based on Gina Fiore’s soon-to-be-released memoir, Advantage Player: A Memoir of Blackjack, Backrooms, and Beginnings from Penguin Random House.

This one has a lot going for it. For starters, I read an advance copy of the book, and it was awesome. Great read, great story. Then there’s the HBO pedigree, which is not nothing. If this thing gets the Sunday night treatment, it has potential to be the next big thing.

Lastly, it stars Riley Keough, who recently starred -- and shone -- in Amazon Prime’s Daisy Jones & the Six. (She’s also Elvis Presley’s granddaughter, which is just such a cool fact.)

Best case: HBO’s next big prestige drama. Emmy Awards. Watercooler show. The whole thing.

Worst case: They miss, and it’s a slog. They treat it more like a gambling story than an underdog story. The gambling comes off as unbelievable.

The Roman

This is another one with outstanding pedigree. This Netflix series is set to star Oscar Isaac as the president of a major Las Vegas casino hotel, navigating the internal battles of running the property and external battles with rival owners.

It comes from Billions creators and Rounders writers Brian Koppelman and David Levien, and Martin Scorsese is executive producing.

Told you there was pedigree.

Best case: Well, Casino meets Billions meets Rounders, I guess.

Worst case: Um … Runner Runner meets Lucky You meets a DraftKings commercial.

The Chop

This one was just announced last week — a biopic on Stephen Matt Morrow, better known as Vegas Matt, who went from advantage slot player to slot influencer with over 1.6 million YouTube subscribers.

Per the Hollywood Reporter, the movie will be written and produced by standup comedian Mike Young. It will center on Vegas Matt’s connecting with a “band of misfit gamblers, and as the collective soon rises to fame, Morrow grapples with the challenges inherent with his success.”

Hmmmm.

Best case: A fun, entertaining, silly romp through Vegas with some drama thrown in. Think something along the lines of 21, maybe. Fine, but forgettable.

Worst case: A slow, boring, ridiculous romp through Vegas with some melodrama thrown in. Think … yeah, Lucky You is catching strays today.

Untitled Shohei Ohtani/Ippei Mizuhara series

This show, announced by Starz, will retell the story of Ohtani’s translator stealing money from Ohtani and betting with it, while Ohtani was a complete innocent in the whole thing.

Feels a little thin for an entire series, if I’m being perfectly honest.

Best case: One of those six-episode, one-season-and-done things, tightly written, sharp, to the point.

Worst case: It’s boring, because the basic story is kind of boring once you know it, and it’s Starz, not HBO, so, you know.

The Baccarat Machine

This one has been in the works since 2020, with Awkwafina set to star in the Kelly Sun/Phil Ivey baccarat story. (It’s a helluva story.)

Will it actually get made? Who knows. But the story is top-notch, and Awkwafina is an inspired choice.

Best case: It gets made and ends up in the gambling movie pantheon.

Worst case: It doesn’t get made. (High hopes for this one, though. Story is too good, Awkwafina is too awesome.)

The Bookie & The Bruiser

This flick starring Vince Vaughn takes place in New York, 1959, and is about a pair of World War II vets — Vaughn, playing an Italian tough guy alongside Theo James as a Jewish bookie — who team up to take money out of the pockets of the Mafia and Irish gangs.

Best case: Goodfellas, A Bronx Tale, etc.

Worst case: True Detective season 2.

Untitled Ocean’s prequel

OK, this one takes place in 1962 and stars Bradley Cooper and Margot Robbie as Danny Ocean’s parents pulling off a heist at the Monaco Grand Prix. It’s written and directed by Cooper, with Josh Gad and Wagner Moura among actors who have signed on.

Best case: Cooper and Robbie as Danny Ocean’s parents pulling off a heist at the Monaco Grand Prix? I mean, inject into my veins please.

Worst case: Cannonball Run II.

Oy. That was a terrible way to end this story. Let’s try that again. Best blooper reel in history.