A Countdown of the 25 Greatest Gambling Movies of All Time: #23 -- "Molly's Game"

Other Oct 27, 2020

This is a daily countdown of the greatest gambling movies of all time ranked from #25 to #1.  Today, we feature #23.

After seeing Molly’s Game, released in 2017, which is writer-producer Aaron Sorkin’s much-anticipated directorial debut, I’m thoroughly convinced he could script his next film based on the Yellow Pages and somehow make it riveting.

A partially-true tale constructed on the weak foundation an almost painstakingly unreadable book published in 2015 of the same title, Sorkin manages to do what I deemed next to impossible — making sweet lemonade out of sour lemons.  He transforms a brassy Heidi Fleiss-like protagonist into a highly-sophisticated and even sympathetic role model/movie hero.  She coaxes our minds and wins over our hearts.  Sorkin’s engaging screenplay, rapid-fire staccato dialogue, and convincing performances throughout ends up coercing us to cheer her rise and console her inevitable downfall.

Most unexpected, this is a stunning achievement.  And so, it belongs among my Top 25 best gambling films.

Molly’s Game, the book written by so-called “Poker Princess” Molly Bloom really wasn’t much of a read.  It was a gossipy, TMZ-tinged blog littered with dirt and scandal plastered between two peak-a-boo covers hustled quickly to press in order to hemorrhage every last dollar out a clump of rumors with the shelf life of last week’s tabloid trash.  

Sure, scandalous tell-all resuscitation has become popular fodder for every genre of American life — from the Mafia to the White House.  Dirty revelations of what happens at by-invitation only, high-stakes poker games frequented by popular entertainers and sports figures is entirely consistent with this lengthy confessional catalog of cattiness we’ve come to digest, and frankly — often enjoy.  

I suppose there will always be an salacious audience anxious to peak through shuttered windows and cross rope lines, eager to read and learn what celebrities are really like behind the scenes in real life.  Hostess-banker-confidant Bloom’s narrative tell-all shattered the firewall protecting several celebs who participated in her weekly poker games — including Tobey Maguire, Leonardo DiCaprio, Ben Affleck, Alex Rodriguez, and other luminaries who frequented the world’s most exclusive man-cave, first in Los Angeles and then later in New York.

Yet for all the lurid details, given the shallow subject matter seemingly better suited for the inside pages of the National Enquirer, Sorkin shocked just about everyone in Hollywood when he announced his intent to direct his first film based on such petty triviality.  Given Sorkin’s haughty pedigree, Bloom’s book made for a baffling starting point.  After all, he’s penned some of the most memorable monologues in recent memory, including television excerpts which have attracted millions of hits on YouTube.  Evidence: “America is not the Greatest” (from HBO’s The Newsroom) and “Based on the Bible” (from NBC’s The West Wing).  Sorkin has also authored a few movie gems you might have seen — including screenplays for A Few Good Men, The American President, Charlie Wilson’s War, Moneyball, and Steve Jobs.  He also won an Oscar for writing The Social Network.

With this expansive resume of ultra-seriousness, Sorkin, a champion of progressive causes and unapologetic proponent of overt liberal activism, could have picked any topic and likely transformed the subject matter into must-see social commentary.  Hence, Sorkin’s decision to turn a blabbering tattle-tale of rich and famous people acting like scumbags into a movie seemed like a misguided decision and squandered opportunity for something far greater given the times we live in.

Well — call me converted and label me now a believer after seeing a marvelously-crafted movie with a brilliant script bolstered by standout performances from Jessica Chastain and Idris Elba.  

The two lead characters and steady elevation of intensity absorbs the audience and never lets us stray.  Consistent with the previous character-driven biographies within Sorkin’s creative wheelhouse, Molly’s Game employs no special effects nor cue music instructing us on how to feel.  The story and characters reveal themselves.  It’s up to us to draw our own conclusions as to how we react and what to believe.  Judgement becomes subjective.

With yet another convincing film role, Chastain once again elevates her well-deserved reputation as one of the most credible actors working in Hollywood today.  She’s “credible” in the sense that every film she appears in — is solid.  Chastain never disappoints.  There are no superhero sellouts, nor blockbuster bombs in exchange for a big, fat paycheck on her movie resume.  Credit Chastain for displaying personal and professional integrity that’s uncharacteristic for most movie stars.  Molly’s Game is a worthy addition to an already fruitful IMDB listing of impressive work from the ginger-haired actress, including Zero Dark Thirty, The Martian, and A Most Violent Year.

Matching Chastain in every single scene is British actor Idris Elba, who plays her attorney.  He’s initially reluctant to represent Bloom in the criminal lawsuit, especially since she can’t pay his hefty legal fees.  But Elba becomes increasingly sympathetic to her plight and ends up convinced Bloom is being railroaded by the Department of Justice with trumped-up charges intended to make her roll over on Russian mobsters who have infiltrated Bloom’s weekly poker games (whether she knew about their real backgrounds is fodder for speculation).  Elba is outstanding.

“Molly’s Game,” is supposedly a poker movie, but really it’s not.  

Poker serves as the stage, but the surrounding arena could just as easily be any setting where an unsuspecting victim gets in way over his (make that her) head, an infectious trap from which there is no escape.  The “game” played here isn’t about cards, at all.  It’s about the people who play them and those who hold the power and always ending up raking in the most chips.  Money might be just a way of keeping score, but in Molly’s Game the ultimate victory comes in achieving unconditional surrender, and even humiliation.

One segment of poker sequences is extraordinary, one of the best portrayals of what this game can do to normal people than anything I’ve previously seen in film.  It shows a wealthy businessman, a player typically adverse to taking large financial risks, a rock-solid poker player going on full-blown tilt after taking a brutal bad beat in a high-stakes game.  Films with poker scenes rarely capture the emotional intensity of the experience of losing.  When this man crumbles right before our eyes, we see a sight all poker players have witnessed countless times before.  The longer we play poker, the more meltdowns we’ve watched, and profited from.  And, if you’ve played poker for a really, really long time, you’ve probably been that decomposing player who emotionally disintegrates into a defeated soul.  Guilty.

Some poker notables have publicly criticized a few scenes.  Mike Sexton (who passed away in September) actually participated in some of the Hollywood poker games portrayed in the film.  Indeed, certain scenes do grossly violate the standard rules of the game.  There’s even been some discussion on social media about why the detail-obsessed Sorkin would get so many things accurate about the real story, but then totally blow it on the poker scenes (mostly, the betting actions are incorrect).  The most convincing rebuttal to this legitimate criticism can be read in poker journalist-writer Robbie Strazynski’s recent article at the website Card Player Lifestyle.  Strazynski’s excellent one-on-one interview with Josh Leichner, who served as the poker consultant for Molly’s Game goes into considerable detail about how various scenes were filmed and why creative decisions were made.  Read the exclusive first-hand account here (“Interview with Molly’s Game Poker Consultant Josh Leichner“), complete with some on-the set photos.

To be clear, Molly’s Game doesn’t merit listing among the pantheon of revealing poker films, although it will inevitably be compared to its iconic forebears.  

While every bit of compelling as Rounders (1998), but not nearly as then-groundbreaking The Cincinnati Kid (1965), there simply isn’t enough poker shown in the movie to group amidst its cinematic brethren.  Rather, this is a story about our quirky legal system, about those who get caught up in the web of hypocrisies, and the unlikely paths we’re forced to take which ultimately shape our lives and determine at our inner core who we really are.

Two minor quibbles with the movie are worth mentioning.  

First, Erba’s character wasn’t real.  Bloom was not represented by legal counsel like the attorney portrayed in the film.  Sorkin thought that adding this character was absolutely essential, and he was right to take artistic licence.  Without Erba in the room to ask the necessary questions and restore some balance as a moral guidepost, this movie wouldn’t have been nearly as watchable (perhaps one of many reasons the book isn’t nearly as good).

Second, the conflict between Bloom and her father as portrayed in the movie didn’t really happen.  A total fabrication gets added to the mix by Sorkin, presumably to enhance her psychological profile and illicit some sympathy.  Kevin Costner in the role of Mr. Bloom, does spice up the drama playing a stern father pushing his daughter to the very limits.  Some critics have taken issue with this emotional padding since it adds perhaps another 30 minutes or so to a movie that clocks in at an unusually long 2 hours and 25 minutes.  However, I thought the fictionalized addition enhanced Bloom’s persona.  I chose to overlook the criticism and think it’s unfounded.

After loathing the book but loving the movie, I remain conflicted as to whether I like or respect Molly Bloom.  No matter.  This movie doesn’t concern itself with ethics nor morality nor make any attempt at winning over my affection.  While told entirely from Bloom’s point of view, and therefore subject to obvious bias, I did gradually find myself rooting for this tough-minded female trying to scratch out a role for herself operating within a wicked world of chauvinism, determined to make it on her own terms and preserve who she is.

Poker can be a game that provides rich rewards far beyond just money when we least expect them, on junk hands that bloom into gold.  In real life, often what we reap is not necessarily what we sow.  Winning can come in different forms, in places where we never expect to taste victory, in the most unlikely settings.  Then and there, we do find ourselves in these crucibles of profound awareness and ultimately, self-discovery.  

Just as with a good movie based on a bad book, there’s no such thing as a great poker hand, that is, until well after we’ve seen the flop.  With Molly’s Game, we initially get dealt two unplayable cards, which end up catching a favorable flop followed by a miracle catch on the turn and river, morphing into the unbeatable nuts.

The Pointspreads.ca Top-25 Countdown (with Links):

#24 – Owning Mahowny (2003)

#25 – The Killing (1956)

You can't play in Molly's game.  So, instead, go make a wager at SPREADS.CA