This is How You Win – Uncut Gems

Adam Sandler is obviously best known for his decades’ worth of roles as an immature man-child, be it in goofball comedies with varying levels of success and quality (I’ll swear by Billy Madison until my dying day, even though I know it’s about as juvenile as all get out), or in something a little more special, like a clever romantic comedy (Punch-Drunk Love) or even an emotional drama (Reign Over Me). It’s in those latter-day offerings that he hints to the audience that there’s a very talented actor behind the schlocky veneer, one that just needs the right material to really shine.

Well thanks to the Safdie Brothers, and their unique skills in the crime thriller space, we finally have that with Uncut Gems. Sandler gives the greatest performance of his career, one worthy of serious Oscar consideration, playing the most perfect version of his singular archetype of a boy playing boy’s games in an adult’s body and world, an unchecked id cast against a civilized – if dangerous and sometimes lawless – society. This is the pinnacle of the very specific character trope that Sandler’s played his whole professional career, put into the exact context where it could have joyous, thrilling, and tragic consequences. It takes visionaries like Josh and Benny Safdie to put this kind of project together, and to wring the absolute best out of a perennial jokester like Sandler and turn him into a serious antihero protagonist.

Set in 2012 (specifically during the NBA Playoffs – I’ll reveal no further to avoid spoilers for sports nuts like me who remember the results), Sandler plays Howard Ratner, a middle-aged jewelry store owner in New York’s Diamond District. He’s a natural hustler who knows how to play precisely to the sensitivities of his high-end clientele to make the biggest sales possible on the most gaudy of trinkets (a gold, diamond-encrusted Furby is one of his hot sellers as the film opens).

He’s also a compulsive gambler, one who owes over $100,000 in debts to his brother-in-law, Arno (Eric Bogosian). His store has a vestibule with bulletproof glass separating the merchandise from the outside hallways and streets, but really it serves as protection for him, as Arno’s hired goons (Keith Williams Richards and Tommy Kominik) keep trying to collect, with increasing violence. Of course, Howard is not a man of just a single vice, as he maintains an affair with his employee, Julia (a wonderful debut for Julia Fox), and even puts her up in his Manhattan apartment while living with his estranged wife (Idina Menzel) and children on Long Island.

This character really is the natural endpoint for all of the repressed man-babies Sandler has played over the years. Learning no real lessons in any of their myriad adventures, it makes perfect sense that eventually they’d grow into the autumns of their respective years as a screaming ego that needs to be placated after never being taught any proper discipline. In your 20s, booze and boobs is enough to mollify, but the addictions get harder and heavier as the years go by, and it’s easily believable that a high-rolling gambling addict would emerge, drunk on the adrenaline rush of cashing in a parlay full of prop bets while spoiling and sexing a woman half his age. I’ve said quite a few times that I tend to judge an actor’s performance by how much I see the character rather than the actor. But here it’s different, because this is Adam Sandler losing himself in a “darkest timeline” version of what Billy Madison or Happy Gilmore could have become long after their original slapstick stories ended. Sandler is electrifying in every scene as he succumbs to – and even embraces – his demons. Arno can literally pounce on him at his daughter’s school play, strip him naked, beat him up, and lock him in his own trunk, and yet somehow Howard (and Sandler by extension) feeds on it. God, it’s exhilarating.

With the aid of his own street tough, Demany (the ever-versatile Lakeith Stanfield), Howard finds himself in a position to solve all of his financial problems. He has procured from Ethiopia a rare and very valuable black opal (the titular “uncut gem”), with an allure that draws in NBA superstar Kevin Garnett, who does a fine job playing a version of himself obsessed with the rock, as he believes he can see the entirety of the universe inside the various gemstones. (side note: Part of me wonders if he got the role because either a) his name sounds like a type of jewel, or b) he was encouraged by his former Celtics teammate, Ray “Jesus Shuttlesworth” Allen from He Got Game). The rock is initially appraised to fetch upwards of $1 million at auction, which would mean Howard can settle all his debts, divorce his wife Dinah cleanly, provide for Julia, and still live a baller lifestyle while recruiting more clients like Garnett. He even lets Garnett borrow the stone as a good luck charm to ingratiate himself (taking Garnett’s 2008 NBA championship ring as collateral… and immediately pawning it). It’s a win-win-win-win-win!

But of course, whenever you gamble, eventually you’ll lose, and really, you lose much more often than you win. The house always has the advantage, which is why Howard likes to do prop bet parlays that bear high rewards if he can hit, but can also be instantly dashed. For example, on two separate occasions, he bets on a multi-tiered parlay that begins with calling which team wins the opening tipoff. That means that no matter what else happens in the game, if the 76ers get the opening tip instead of the Celtics, the entire bet is void, and he’s lost tens of thousands.

But that’s the rush he gets, and no matter how dire things get, no matter how far into the weeds Howard finds himself, no matter how much his life and the lives of his family members are put at risk, it’s all worth it for the big score, and God love the Safdie Brothers if we don’t feel that suspense viscerally the entire way through. Even when it finally looks like he’s going to come around and do the right thing, if nothing else than to just save his own ass, he just can’t let a chance to strike it big slip by. He can’t resist the temptation of a little taste of glory. It’s not even about the money. It’s about an obsession with the victory itself, with winning, and even though the film is set in 2012, it’s a theme and a danger of which we’ve seen the real-world effects here in 2019.

Now, the film has its flaws, certainly. For my part, there were a few too many Jewish stereotype jokes. I get that it’s all internal, and everybody breaks balls, but it got to be a bit much. Sandler does his best ever work in this film, but even he can’t resist the urge to throw a goofy voice on when he’s reading the script at Passover seder. There’s also a wholly unnecessary cameo by The Weeknd. I love his music, but just like with Kid Cudi in Jexi, musician cameos are just tacked-on tackiness as far as I’m concerned. To be fair, though, at least they remark that The Weeknd is “up and coming,” since the film is set in 2012 and his breakout hit, “Can’t Feel My Face,” wasn’t released until 2015 and his debut album came out in 2013. If you’re going to shoehorn in a cameo, at least make it appropriate to the plot and timeline, so kudos to the Safdies for that.

Finally, it’s a plot hole that I’m sure was overlooked for the purposes of product placement, but the climactic wager of the film is placed at Mohegan Sun casino in Connecticut. I used to go there all the time when I lived back east. Mohegan Sun has no sports book, because sports wagering is not legal in the state of Connecticut, even on Indian reservations. They have a race book, just like their neighbor and competitor Foxwoods, but no sports book. Maybe there’s a deleted scene somewhere that establishes an allowance for high rollers to skirt the rules, especially if it makes the casino a buttload of money, but I’m not holding my breath to see it. One, it would be clunky exposition, and two, I’m pretty sure Mohegan wouldn’t want to put their name on something patently illegal, even in fiction. It just seems like a bad image. Story-wise, my guess is that the situation arises because the script paints Howard into a corner where can’t wager with his normal bookie Gary (New York sports radio personality Mike Francesa) after Arno intervenes, but I have to think there could have been another way around it, maybe a trip to Vegas or something. It’s not a giant plot hole, but as a degenerate gambler myself, it’s one that stuck out to me.

Really, though, I just needed two paragraphs to explain why this isn’t the best film of the year, but it is up there. Again, we always kind of knew Adam Sandler could act. We’d gotten hints and spurts of it here and there for the last 25 years, even when he’s yelling in fake Yiddish at a man in a penguin suit or getting his ass kicked by Bob Barker. You knew there was something there. Well this is the culmination of a quarter century of unrealized potential.

It’s weird. People are chomping at the bit to nominate Jennifer Lopez for an Oscar for Hustlers, which just terrifies me in the abstract (I haven’t seen it yet, and I swear I’ll give it – and her – a fair shake if she does in fact get a nod). I just shudder to think that I’d ever have to see or say “Academy Award Winner Jennifer Lopez,” because even if Hustlers is her best performance, it’s not like there’s been any real quality beforehand to suggest she’s actually a competent actress. It feels more like they want to reward her for finally doing something that doesn’t suck out loud, like they’re grading on a kindergarten curve where tying your shoelaces right just once gets you all the gold stickers. Again, that might not actually be the case, and maybe she’s terrific in the movie. I’ll know when and if I have to see it. But until that day comes, it just feels wrong.

On the other hand, we’ve seen flashes of brilliance with Sandler over the years that make his note-perfect turn here believable and almost natural. Yes, the bulk of his catalog is decidedly on the shitty side, but we’ve seen that he can do great things with the right material. We were just waiting for that perfect storm moment to bring it all together, and with Uncut Gems, we have it, and it’s so so SO good that I would have no problem saying, “Academy Award Winner Adam Sandler” if he got rewarded for this.

God knows I never thought I’d say that.

Grade: A-

Join the conversation in the comments below! What film should I review next? What other actor would you like to see elevate themselves to prestige level? Is it maturity or just good directing that Adam Sandler sees his character’s name tattooed on his girlfriend’s ass and somehow doesn’t say, “Want to touch the heinie”? Let me know!