Getty Images / Frederick M. Brown

Despite an extensive track record of films that could make Rotten Tomatoes ponder getting rid of negative ratings, don’t be surprised if one of the best performances of 2018 comes from one of the most unlikely actors: Adam Sandler. That might seem akin to proclaiming a broken clock right twice a day.

However, news has emerged that some of the most promising young directors in Hollywood, Josh and Benny Safdie, whose latest, Good Time, currently sits at 92 percent on Rotten Tomatoes, have cast Sandler in their hotly-anticipated follow-up, Uncut Gems.

While one might think that the bold directors have youth and gumption on their side as it relates to evoking a strong performance out of Sandler, in reality, there is actually tangible precedent; Sandler has a history of following up a string of schlocky, profitable films with an outstanding performance.

Sandler’s career has not exactly been that of a master thespian, but it has certainly been lucrative. A five-year breakout stint on Saturday Night Live launched a movie career that would span decades of box office relevance and has been incredibly profitable for both Sandler and his investors. Even though his recent Netflix films aren’t exactly critical darlings — Ridiculous 6 has an unbelievable 0% on Rotten Tomatoes — they have been great for the streaming giant. Ridiculous 6 was the most watched film in Netflix history at the time of its release.

Critically panned and commercially successful has been the theme of Sandler’s career. While Sandler’s early comedies Billy Madison and Happy Gilmore remain cult hits, it’s difficult to find a beloved film among the comedies he has produced since founding his production company, Happy Madison, in 1999 (besides Funny People, which was an Apatow Films co-production).

Comedy is clearly where Adam Sandler feels most comfortable. He’s even admitted that many of his projects are an opportunity for he and his oft-collaborators/friends like Allen Covert, Rob Schneider, Nick Swardson, Steve Buscemi, David Spade, Kevin Nealon, and Chris Rock an opportunity to hang out.

Although the plot of Uncut Gems is being kept under wraps, it promises to be another unique thriller like the Safdie’s previous film, Good Time, which also has Martin Scorsese as a producer, and A24 having secured worldwide rights, who released critical fare in 2017 like Lady Bird, The Disaster Artist, The Florida Project, Good Time, and won an Academy Award for Best Picture a year earlier for Moonlight.

It will take a special performance to earn Adam Sandler an Oscar nomination, but there is enough material in his past to suggest he is actually capable of a breakout performance, putting him in the company of actors like Leonardo DiCaprio and Sandra Bullock who both went from Razzie to Hollywood’s highest honor.

A close look at his career also begs a larger question: why does a man so capable as an actor sign on to so few quality projects? Why does someone who can stand out in the films of auteurs like Paul Thomas Anderson and Noah Baumbach reliably go back to putting out films that are critically panned? A survey of his career reveals a clear pattern, but in some ways raises more questions than it answers.

The Wedding Singer (1998)

It’s easy to forget The Wedding Singer when there are far more serious roles in Sandler’s filmography, but his turn as Robbie Hart was his first attempt at flexing his dramatic chops. Though the part still maintained a measure of his trademark humor and boyish charm, and the film itself featured memorably hilarious bits from Jon Lovitz and Steve Buscemi, The Wedding Singer is far more rom-com than broad comedy. The pain that Hart exudes in the early scenes of the film is far more earnest than any conflict he dealt with in Madison, Gilmore, or The Coneheads.

With The Wedding Singer, Sandler set out to reset his image, and he did just that. Leonard Klaby wrote in his Variety review, “Sandler, whose screen persona has been somewhat grating, is a revelation playing a character with innate decency. Unlike in past film work, you believe him as a romantic character and, even more important, that someone else would find him attractive. It is, quite simply, a break-through performance.”

What Sandler did next was incredibly odd for someone who had just had a “break-through.” After breaking through, he decided to retreat. His next major films were broad comedies with limited critical appeal (and that’s putting it nicely): Waterboy, Big Daddy, Little Nicky, and Mr. Deeds.

Punch-Drunk Love (2002)

Following another string of critical flops that would combine to bring in hundreds of millions of dollars, Sandler once again got the itch for critical recognition. This time he upped the ante. Rather than simply doing another rom-com, he partnered with arthouse favorite, Paul Thomas Anderson, for what many consider to be his finest performance as an anger addled novelty salesman in Punch-Drunk Love.

It’s worth excerpting A.O. Scott’s full description of Sandler’s performance in his New York Times review, because the glowing assessment of his work is typical of the critical reaction to the film. His work in the film got Sandler a Golden Globe nomination and earned Anderson the Best Director award at Cannes:

“It might be have been interesting if Mr. Sandler had departed from his usual doofus man-child persona, but what he does within that persona — infusing it with a vulnerable, off-kilter humanity that recalls such great film comedians as Buster Keaton and Jacques Tati — turns out to be even better.

He has often used the possibility of violence that accompanies his charm to crude, bullying effect, most recently in the horrendous Mr. Deeds. But here, because the spectacle of Barry’s cowardice is so excruciating, and the injustices and annoyances he suffers so stressful, Mr. Sandler’s fury comes close to poetry.”

With such high praise, you might think that this would mark the dawn of a new era for Sandler. You would be wrong. The stretch between Punch-Drunk Love and his next more serious role in Funny People was seven years long and yielded some of the worst films ever made, such as Click, Don’t Mess with the Zohan, and I Now Pronounce You Chuck and Larry.

At that time, and perhaps for the rest of his career, Paul Thomas Anderson will have his choice of A-list actors who have earned Academy Award nominations in his films –  before and after Punch Drunk Love –  like Tom Cruise and Daniel Day-Lewis. The director clearly saw something in Sandler, as did another notable film critic, Roger Ebert, who predicted a future for Sandler in “Dennis Hopper roles” based on his ability to emote “darkness, power, and obsession.”

Funny People (2009)

Of Sandler’s serious turns, the Judd Apatow-directed Funny People might be the least successful, but in the context of Sandler’s career and self-perception, it might be the most interesting. In Funny People, Sandler plays himself, or, more accurately, the version of himself he would like us to believe. The autobiographical strains of the film are palpable throughout. Sandler plays a stand-up comic who now takes huge roles in hackey broad blockbuster comedies. He has reached a crossroads in his career and wishes to return to his roots.

The feeling of memoir in the film is only heightened by the fact that Sandler and Apatow used to be roommates in real life. Funny People draws so intentionally on real life and the trade-offs that come with stardom for both Apatow and Sandler that Indiewire’s David Ehrlich has gone so far as to call it, “The Great Gatsby of the 21st Century.” It bears mentioning that Erhlich’s is a recent appraisal. Critics at the time weren’t so kind.

The New York Times in particular was not buying the prestige act this time around. Perhaps it was the overlong run time. Perhaps it was the “on the nose” bid for respectability. Whatever it was, Manohla Dargis, like many critics, was unconvinced:

“That’s too bad because while Mr. Sandler doesn’t have the necessary acting technique or even the natural warmth to convince you that his character cares about anyone else, he is undeniably a star, the movie’s biggest draw and its most effective and powerful presence. It’s easy to buy him as both a selfish jerk and a maudlin self-pitier, whether George is weeping alone into his designer sheets or confiding some medical news to his housekeeper, the only sympathetic ear around. With his flatline drone, stand-and-deliver gestural performance and prickliness, Mr. Sandler is effortlessly charmless, and in his performance you see the risky movie this might have been if Mr. Apatow had pushed harder.”

After Funny People, it was back to business as usual. In the last decade or so, Sandler has brought us such critical failures as Jack and Jill, Grown Ups, Zookeeper, and Pixels. It is very difficult to determine if Sandler’s movies were worse between 2002 and 2009 or between 2009 and 2017. I’ll leave a deep dive into that question for a stronger person than myself.

The Meyerowitz Stories (2017) and Uncut Gems (2018)

As if on schedule, the last year or so has brought with it another serious bid for respectability from Adam Sandler. However, The Meyerowitz Stories, a Noah Baumbach film about a dysfunctional New York family (it is, after all, a Noah Baumbach film), didn’t quite catch the cultural zeitgeist in a crowded indie field led by Lady Bird, Get Out, Good Time, and The Florida Project. Sandler’s performance though was once again critically acclaimed.

Peter Debruge of Variety loved Sandler’s performance, writing, “With no schtick to fall back on, Sandler is forced to act, and it’s a glorious thing to watch — even for those fans who like him best in perpetual man-child mode…”

Sandler signing on to another prestige project right after a dramatic turn isn’t like him, but that’s exactly what he’s done with Uncut Gems. If Sandler is looking for a little more attention than he got for Meyerowitz, working with the Safdies is probably a good choice. The brothers transformed Robert Pattinson’s teen matinee idol image into that or a serious actors with Good Time, so helping Sandler with another bid for respectability should be no problem.

Why Does Adam Sandler Keep Making Bad Movies?

The bigger question that remains is if this marks a real career shift for Sandler, or merely another pit stop in the midst of a steady stream of schlock. While his tortured sad clown character in Funny People makes for a compelling story, that doesn’t seem to be Sandler’s situation. If he wanted to walk away from the broad comedies that have made him an incredibly rich man, he could have done so after Grown Ups, let alone after Grown Ups 2.

Of course, the easiest motivation to see is the money. Sander reportedly makes in the neighborhood of $20 million per film. That is roughly the entire budget of Punch-Drunk Love. Additionally, some Sandler films are said to have upwards of 50 product placements, which further increases his payday. Forbes estimates his annual income at $50 million, and various sources have put his net worth around $350 million.

Couldn’t Sandler make more good movies, considering he could finance any number of indie auteurs with one year’s income? If Sandler is really in a prison of his own making, isn’t he still the warden?

There is another theory. A 2015 analysis of the miserable box office performance of Pixels from Variety offers a different rationale for his career moves. Maybe it isn’t that Sandler has a secret desire for respectability. Maybe he knows that periodically, he has to do a respectable film to keep the Happy Madison machine running. Two of the five reasons the article offers for the Pixels flop are “He’s not edgy” and “Is he even trying?” A few prestige performances or an awards nomination could change that perception overnight. Could the good performances simply be a plan to perpetuate the terrible ones forever?

There are two ways to view Sandler’s career, and critics have made both arguments. Either he periodically appears in prestige projects as a brand-building detour from his main pursuit of soulless money making or he is a frustrated “serious artist,” who is rarely offered more serious opportunities. You don’t have to look far to find arguments like The Washington Post’s Michael E. Miller’s “Adam Sandler is awful, and it’s our fault,” in which he claimed Sandler “was stung by poor box office response to his more serious roles.”

Only Sandler knows which of these is true, or if it is a little bit of both. All we have to look at is a career in which an actor who appears in a prolific run of terrible movies gets a seven-year itch for prestige, and earns critical adulation, only to go back to the schlock he was doing before. Every few years, Adam Sandler gives us a performance that looks like it might change the trajectory of his career, but then a sequel to Little Nicky or Don’t Mess With the Zohan beckons and he just can’t help himself.

We might have to wait until he has told his last fart joke and hung up his prosthetics for a full appraisal of Sandler’s career. It might take a memoir or biography to get at the root of his career choices. Maybe Sandler himself doesn’t have an answer.

But one thing is for sure: if this past is any indication, the critics are going to love Adam Sandler in Uncut Gems.

Words by Brenden Gallagher

Brenden Gallagher is a freelance writer and TV drama writer based in Los Angeles.

What To Read Next