By Earl Burton - Apr 9th, 2017. It isn’t very often that movies about gambling – and especially poker – come across any of the forms of media from Hollywood. Last updated on Sep 9, 2017; Play all Share. Sign in to YouTube. Action Movies The Last Casino 2014 Full Action Movie Best Action Movies by Betsy Mariel. Molly’s Game is another film about gambling based on a true life story. The 2017 film starring Jessica Chastain, which I saw in Philadelphia, was based on Molly Bloom’s memoir with the same title.
It isn’t very often that movies about gambling – and especially poker – come across any of the forms of media from Hollywood. Arguably the best known of this genre is the seminal poker film Rounders and there are few other examples that would compare (for comedy, check out The Grand and, to help Matt Savage’s retirement fund, go for Lucky You). A new effort that didn’t even go to the silver screen is now drawing attention for its realistic look at gambling and poker.
One of the best things that has come from the streaming services such as Hulu, Amazon Prime and Netflix is that they are now developing their own programming. That’s where a fan of gambling films can find Win It All, streaming on Netflix basically any time that the viewer wants to watch it. The movie has a 95% approval rating on the movie website Rotten Tomatoes (based on 20 reviews) and an average rating of 7.5 out of 10, while it also garners a 78 (on a scale of 100) on the website Metacritic.
The movie focuses on Eddie Garrett (Jake Johnson, known for his work on the Fox comedy New Girl), a gambler whose day job is parking cars at Wrigley Field in Chicago (for anyone who has ever tried to park in the neighborhood surrounding the home of the Cubs, you’ll understand the job) and who by night is, as his Gamblers’ Anonymous sponsor Gene (Keegan-Michael Key of the Comedy Central program Key & Peele), someone who has “never won.” But things are about to change for Garrett after he does a favor for a friend of his named Michael (Jose Antonio Garcia): hold onto a duffel bag while he is incarcerated, but don’t look inside it.
While it should be easy to do a favor, curiosity gets the better of Eddie and he eventually cracks open the bag to find a crapload of money inside. And, naturally, because he is a compulsive gambler, Eddie eventually blows the money in the bag through a variety of gambling means. Where the twist comes to the movie is when Michael calls Eddie from prison to let him know that he’s being released early and Eddie must come up with the money that he’s lost in the only way he knows – gambling.
The premise may not be appealing to those who consider themselves “professional gamblers,” but Win It All works because of the directing of the film. Director Joe Swanberg gives the film a great look at how the underground gambling scene works (he also films it very well), but Swanberg also doesn’t shirk scenes away from the “world of gambling.” Win It All is as much a look at the gambling world as it is a glimpse into the mind and psychology of a person who tries to do the right things but sometimes steps awry.
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It may be a better effort than what could be coming down the pike soon. Screenwriter Aaron Sorkin has finished his directorial debut in Molly’s Game, his adaptation of “The Poker Princess” Molly Bloom’s story of working in the world of underground poker. The story of Bloom is well known to most in the poker world, how she went from a former Olympic hopeful to the organizer and host for the biggest high stakes cash games in first Hollywood and then New York. The problem with Molly’s Game? Sorkin doesn’t plan to tell the whole story.
On many occasions, Sorkin has stated he will not delve into the players who took part in the games, going as far as to not name them at all. That would mean ignoring (or at least putting on fictitious players) vast swaths of Bloom’s book where she talks about such power players as Leonardo DiCaprio, Ben Affleck, Tobey Maguire and other Hollywood producers and businessmen. Sorkin has also said that Molly’s Game isn’t about the poker but about “Bloom’s journey to finding who she is.”
The problem for Molly’s Game is that it has lined up some A-list talent for what might be a horrendous story. Two-time Academy Award nominee Jessica Chastain will play Bloom, with Idris Elba slated to play her attorney and be a major plot driver. Others such as Kevin Costner, Michael Cera and Jeremy Strong are also a part of the project, which is slated for release later this year.
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Until the Sorkin film premieres, we might have to do with Win It All to satisfy the jones for gambling movies. If the reviews are correct, it may be the better of the two films.
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In the third collaboration between Joe Swanberg and Jake Johnson ('Drinking Buddies,' 'Digging for Fire'), chronic loser Eddie (Johnson) tries to get his act together, encouraged by his long-suffering brother, his Gamblers Anonymous sponsor, and a new romantic interest. Eddie doesn't have a job. He plays poker at night. He's always strapped for cash. From the way his brother Ron (Joe Lo Truglio) treats him, you can tell that Eddie has always been a problem, the guy who needs a loan, the guy with grandiose unrealistic plans, the guy who can't settle down.
The inciting incident of 'Win It All' occurs when a scary gangster-type named Michael (José Antonio García) asks Eddie to hold onto a duffel bag for him while he does a stint in prison. He'll pay Eddie $10,000 just for keeping the bag safe. However: Eddie is not allowed to look in the bag. Eddie agrees to this condition, assuming it will be the easiest money he ever made. Michael has to know that Eddie will not be able to resist looking in that bag, right? Michael has to know that if, for example, there happened to be wads of cash in that duffel bag, then leaving it in Eddie's care would be the same thing as throwing the money away?
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The inevitable happens. ('Oh no ... oh no ...' Eddie half-laughs half-moans, when he looks in the bag and sees the piles of money.) And of course, he decides to gamble just a little bit of it, so he can pay off some debts. This goes as well as can be expected and the situation very quickly careens out of control. (Occasionally, a calculator counter shows up on the screen, showing how much he's up, how much he's down.)
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'Win It All' proceeds in a pretty predictable fashion (mainly because gambling proceeds in a predictable fashion). This is a story we all know already. Good movies about gambling ('The Hustler,' 'The Gambler,' 'California Split,' 'The Sting,' 'The Cooler,' to name a few) deal with high-stakes pressure, the mindset of gamblers, the magical thinking involved (and required). To someone who has no interest in gambling, there's something queasily awful about watching someone not know to quit while they're ahead. 'Win It All' has a couple of entertaining sequences with an improvisatory spontaneity that—when it works—is the best part of Swanberg's low-key style. But overall, the film feels very slight, wispy-thin, barely there. 'Win It All' also has an extremely obtrusive soundtrack, but the music can't create the urgency that the film really needs.