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‘Funny People’ Is An Underrated Masterpiece, And Adam Sandler’s Latest Misfires Make It Even Better

Not only is "Funny People" better than you think, it's also "The Great Gatsby" of the 21st century.

“Funny People”

I’ve watched “Funny People” more times than I care to count (fun fact: Judd Apatow movies comprise roughly 40% of all cable television programming), but it never occurred to me that Apatow’s raw, shaggy, desperate masterpiece of a third feature was inspired by “The Great Gatsby.” For some reason, I didn’t automatically make the connection between The Great American Novel and a studio comedy in which Adam Sandler has sex with a stranger while pretending to be a Merman. But someone recently pointed out the parallel, and — like a Magic Eye stereogram or that bump on Jean-Claude Van Damme’s forehead — it’s the kind of thing that you can’t un-see

Ira Wright (Seth Rogen) is our new Nick Carraway, an aspiring L.A. comedian who forms an unlikely relationship with a lonely, enigmatic, semi-reclusive titan of his industry. George Simmons (Adam Sandler) is our Gatsby, a mega-successful movie star whose fame and fortune have distanced him from the world beyond the walls of his empty Hollywood mansion. Simmons, like Gatsby, has made too much money on vapor; he’s spent so long buying the human connections that most people typically have to earn.

And Simmons, like Gatsby, finds himself increasingly preoccupied with the girl who got away — his Daisy Buchanan is a retired actress named Laura (Leslie Mann, Apatow’s wife), a married mother of two who lives up in Marin County with her philandering Australian husband. Gatsby’s signature line: “You can’t repeat the past? Why of course you can!” George Simmons’ signature movie: “Re-Do,” in which he plays an adult man who’s magically transported into the body of a baby after he runs afoul of a rogue wizard. F. Scott Fitzgerald practically deserved a credit on this thing.

Of course, the tension between the drag of the past and the thrust of the future is a theme that isn’t strictly limited to the works of Apatow and Fitzgerald, but it’s interesting how the former explores that theme through the lens of modernism, while the latter does so through the herbal haze of man-children.

If “The Great Gatsby” is preoccupied with the decline of the American Dream, with the tenuous dynamic between progress and excess, “Funny People” refocuses those same undercurrents into a study of the uneasy balance between adolescence and adulthood. It includes a scene in which a stand-up comic named Raaaaaaaandy (Aziz Ansari) compares Cold Stone Creamery to a crack dealer, and it also includes a scene in which George Simmons silently contemplates his own mortality while listening to Warren Zevon’s soul-shattering “Keep Me in Your Heart.”

This isn’t Apatow’s most likable film, or his most purely enjoyable; it’s hard to compete with “The 40-Year-Old Virgin,” which set the tone for a new generation of mainstream comedy, or “Knocked Up,” which galvanized that generation into something sustainable. All the same, “Funny People” is the most unapologetically honest and heartfelt expression of an idea that has been at the core of every movie that Apatow has ever made about men and their tendency to self-infantilize when confronted with the challenges of adulthood. 

“Funny People” feels like an open wound from the moment it starts, deeply personal for both the man behind the camera and the star in front of it. That intimate edge is present from the opening credits, which play over home video footage of a young Sandler — a few years shy of “SNL” and the fame that followed — making crank calls from his living room (fun fact: the footage was actually shot by Apatow himself, who used to be Sandler’s roommate). It’s a strikingly confessional gambit, the movie going out of its way to conflate Sandler with George Simmons from the very start. And the self-ashamed implications of that association soon become obvious to anyone who’s even remotely familiar with Sandler’s work: Both men have more money than they could ever hope to spend in one lifetime, and both men have earned that money by sacrificing their comic genius at the altar of soulless Hollywood dreck.

Back then, of course, it was natural to assume that “Funny People” was Sandler’s thinly veiled mea culpa for his own mediocrity, that he was vowing to do better going forward. We knew that it could be singularly exciting to see the comedian step out of his comfort zone, we knew that the best moments of his big-screen career had all resulted from lending his persona to great filmmakers and allowing them to subvert it however they chose, and we were still waiting for Sandler to do that on a more regular basis. The natives were understandably growing restless after a streak of clunkers that included “Click,” “Bedtime Stories,” and “I Now Pronounce You Chuck and Larry.”

Sandler didn’t quite see things that way. While he obviously recognized the parallels between himself and George Simmons, he refused to consider them as a tacit admission of guilt. In fact, he refused to think about them at all. “This guy that I play is leading a different life than I live,” he said at the time of the film’s release, helpfully explaining how the basic concept of acting works.

Digging back into the film’s press tour and reflecting on the project in light of what Sandler has done since, it starts to seem as though the comedian wasn’t confronting the mistakes that he’s made so much as celebrating the ones that he hasn’t. The film doesn’t build to an admission of guilt, and Simmons never rededicates his life to making better art. The movie didn’t spark a compelling new chapter of Sandler’s career; it only precipitated a series of bold new lows that began with “Jack and Jill,” led to “Pixels,” and culminated with a lucrative Netflix deal that made his diseased brand airborne. For Sandler, George Simmons’ career was less of a cautionary tale than it was a source of inspiration. The worse that his career gets, the more compelling “Funny People” becomes: Three films into his Netflix contract, the movie is now a bonafide masterpiece.

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