As the past few weeks of heartfelt memorials have demonstrated, Garry Shandling was a towering force whose influence is reflected across the modern comedic landscape. As the creator of the It’s Garry Shandling’s Show and The Larry Sanders Show, he can be traced as one of the pioneers of both the current era’s age of meta comedy and the subtle vein of misanthropy that runs through this generation of comedy television. But expectedly, very few people have devoted much ink to his movie career.

Despite roles in films from directorial legends like Mike Nichols and Nora Ephron, Shandling’s movie career is checkered. In fact, it’s speckled with such notorious misses that The A.V. Club’s own Nathan Rabin has written about two of Shandling’s most high-profile roles for his ongoing My World Of Flops series: the battle-of-the-sexes comedy What Planet Are You From? and the star-studded sex farce Town & Country.

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As Larry Sanders, Shandling predicted the oncoming generation of leads whose empathy came less from aspiration than a familiarity with the reality of what happens when the mask comes off. Through unsparing writing and Shandling’s own fragile onscreen persona, Sanders subverted surface notions about the glamour of stardom. He offered a Dorian Gray-esque look at the ego-preening and relentless pessimism that emerge from trying to entertain people nightly, and gleefully illuminated the divide between perception and reality. But Shandling’s self-inquisition didn’t stop with Larry Sanders; it followed him deep into his movie career.

Generally, Shandling’s movie roles fit one of three categories: vanity appearances that rely on a viewer’s outside knowledge of his persona; fly-over cameos in random indies; and star-studded farces driven by a voracious sexual appetite. Shandling’s latter-day appearances usually fall into the first category, in examples such as Zoolander, The Dictator, Run Ronnie Run, and his oddball casting an insidious senator in Captain America: The Winter Soldier and Iron Man 2.

These appearances weren’t traditional movie roles for someone known for acting, and yet they felt perfectly on brand from someone who’d spent a lifetime creating a persona whose hollow sense of fame was often the point. Zoolander, for instance, has a reputation for its parade of celebrities, but it’s still strange to note that Shandling’s split-second thumbs-up comes after Fred Durst, Lil’ Kim, and Lance Bass—a trifecta of pop-culture icons whose outsize personas loom over their individual contributions to music.

These one-scene walk-ons serve as an unfortunate posthumous symbol of Shandling’s inability to become a movie star. And, as his career retroactively demonstrates, even in the rare occasions when he was the lead, he couldn’t transcend the audience’s understanding of his persona.

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Unusually, it’s not even a live-action role, but a supporting role in an animated feature, that best explains why Shandling never became a movie star. In 2005, he played second fiddle to Bruce Willis in the mildly clever Dreamworks creature caper, Over The Hedge. As Verne, a nebbish turtle, he doesn’t exactly turn in a scene-stealing vocal performance. Placed into a computer-generated character, Shandling is nearly invisible, shorn of all of the alluring contradictions between his body language and vocal delivery. Filled with quaking hesitation and other vocal tics, he sounds so similar to latter-day Billy Crystal that it’s enough to inspire a double-take.

Based only on surface parallels, both Crystal and especially Albert Brooks seem like inevitable contemporaries to Shandling. And while it’s foolish to lift up looks as a basis of the ability to become a movie star or not in the fickle world of Hollywood, it can’t be completely overlooked that none of these comedians fit the characteristically refined features of the modern movie star. It’s also certainly not incidental that all three came from stand-up comedy backgrounds before transitioning into screen roles that allowed them to cultivate very specific sensibilities.

Shandling has never been a traditional crowd-pleaser, despite becoming an early fixture during the Johnny Carson era of The Tonight Show alongside popular comedians like Steve Martin, David Brenner, and Brooks. Even outside of his own shows and filling in for Carson, Shandling as a host communicated an underlying sense of discomfort, whether he was playing to the crowd for a one-liner or ingratiating himself with guests. Crystal, by contrast, has his own sense of anxiety, but it’s deeply ingrained into his shtick, as if he’s always nudging the audience while he’s falling to pieces in front of them. It’s a persistent energy that’s present in both his stand-up and his movie roles like City Slickers. Shandling was the sad clown, while Crystal had such a manic energy that any semblance of longing or alienation was completely overshadowed.

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Brooks is a more apt comparison in both their akin manners as outwardly cantankerous personas and their creative trajectories. And though Brooks may have had a more successful overall film career (Shandling certainly never had either a critical success like Broadcast News or a populist phenomenon like Finding Nemo), they both also served as their own greatest muse.

In the salad days of his directorial career, Brooks was crafting singular, beloved pieces of work like Modern Romance, Real Life, and Defending Your Life. His onscreen persona was a constant bundle of nerves—a curmudgeon whose cynicism was buffered by an old-fashioned romanticism. Shandling, likewise, was the most prominent creative voice of two massively influential television shows. His onscreen persona was less harsh, but still sour. With his sheepish, droopy dog smile, Shandling hid a loneliness and hurt—a quality that never quite disappeared even as his shows ended. Brooks had his prickly, irascible persona, but he could find a way to slip into his characters. Shandling, on the other hand, seemed to always be playing a variation on himself.

In his television career, Shandling offered a backdoor into Hollywood—a peek into commercial-break temper tantrums and the deep wells of pettiness that fester with extended exposure in the spotlight. Sanders’ murmured unease conveyed unspoken vulnerability, as the audience was able to see a million different opposing forces. Playing a fake host on a show that mirrored his past as a staple of The Tonight Show, Shandling was perfect as Larry Sanders. He could easily put up the charmed facade, all while his private life was a mess of neuroses and dissatisfaction. His awkward small-talk and rictus grin was a quintessential encapsulation of the gulf between the backstage and the spotlight.

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But Shandling’s sensibility never quite meshed with Hollywood or with narrative movies. On the big screen, he was never meant to act as an ongoing commentary on the material. But he couldn’t just exist within the roles either. His characters felt like they had separate, more melancholy interior lives that contradicted the general goofiness of the parts as written. Even in his most ingrained roles, Shandling still feels adjacent to the respective movie—an intervening force that nearly always broke down the fourth wall. He was the rare actor who wasn’t a movie star but still had such an established, distracting presence that the world a film established would shatter whenever he appeared.

It’s perhaps only inevitable then that Shandling’s most prominent roles have been in movies that elevate madcap comedy into a nearly dada art form. These are movies that are pitched at such a consistently abrasive level that the actor’s arrival is just another element of the chaos. You can’t quite identify Shandling as traditionally good in these roles, but he’s often memorable, if only because his line readings are delivered with such gratuitous self-awareness that he sounds like he beamed in from another planet.

And yet the most inexplicable part about Shandling’s domination of scenes is that his performances are more accurately identified as understated than hyperactive. In Town & Country, Shandling plays a soft-spoken, neurotic antiques dealer slowly coming to terms with his homosexuality, and yet somehow that subplot feels more frazzled than nearly anything else in the movie—which speaks volumes, given that there’s also a scene where Charlton Heston threatens Warren Beatty with dragon noises after finding him with his daughter, simulating sexual positions with two teddy bears.

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Nichols’ What Planet Are You From?, which counts as Shandling’s only real starring big-screen vehicle, features an equally outsize performance by the actor. But it functions nearly opposite from the tonal ambitions of Town & Country, with Shandling diminishing himself to a nearly catatonic somnolence as an unfeeling alien who needs to seduce human women. Even by the end, when Shandling’s character is supposed to be happy and satiated, there’s still something ineffably remote about his character—an imprint of Shandling’s own scattered personality.

Even in the notorious ’90s Nora Ephron ensemble piece Mixed Nuts, Shandling is able to infuse an unexpected poignancy and weirdness into roles that could have been nothing in other people’s hands. Mixed Nuts is an eight-car-pile-up of bad ideas, but Shandling’s single scene as a sycophantic landlord is a welcome reminder that few people could deliver perverse, absurdist lines (“Does anyone ever drink glass?”) with such anxious glee. And even fewer people could make a character that has less than 20 lines feel so gloriously unhinged.

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In the weeks since Shandling’s death, many have mourned a creative resurgence that never happened. Beyond even the hypothetical involvement of Steven Soderbergh or Quentin Tarantino, auteurs known as much for their career rehabilitations as their bodies of work, it’s not impossible to imagine Shandling’s comedic styling finding a place in modern Hollywood. This is an environment where comedic enigmas like Bill Murray have built entire careers off the subversion of their own identities.

It’s now a case of wish-fulfillment, but it’s not difficult to imagine what a modern director interested in the gulf between perception and reality could have done with Shandling. What great, acidic Charlie Kaufman or Rick Alverson movie could have been made from molding Shandling’s personality or digging into his contradictions? He deserved more than a walk-on role in a superhero movie, or a fleeting moment as a victimized health inspector. He had earned his own place in the comedy conversation—not just as a pioneer, but as a comedian who knew how to mutate his own fluidly meta identity.