With a solid collection of paintings currently attracting lots of attention on view at the swank Upper East Side townhouse Acquavella Galleries, and an exhibition of mainly self-portraits coming this October to the Royal Academy in London, (which, if it were up to me, would be titled: “Me, Myself, and Everything They Say About Me”), it is time for me to say everything I think about the despicable genius, Lucian Freud.

Do I see Freud as a harmless academic painter, lodged in the annals of art history like a trophy on a mantle collecting dust—even if there is no dust in museums? Is Freud a notable Brit worthy of being ceremoniously draped with a medal and given the title Sir (or Lord), but, alas, an irrelevant old geezer from the get-go—only talked about in the discourse being had by smock-wearing, squinting, middle-aged Old Masters?

No matter how regressive or irrelevant a painter you think he is, you have to admit Freud has always made headlines. According to one tabloid journalist, back in his prime, Freud did well with women, snagging the gorgeous socialite Lady Caroline Blackwood. She became his second wife and the subject of many early portraits, but also ushered him into the jet set, and off to Paris to flirt with the likes of Picasso. Another gossipy writer offered that Freud is believed to have sired somewhere in the double digits illegitimate children with countless mistresses. I also read somewhere online that Freud inked a million-dollar bird tattoo on the supermodel Kate Moss’ dimples of Venus. (It seems to have occurred when the two were palling around—Kate was pregnant and modeling for a painting.) You might say Freud was grandfathered in to the “over 80 and still pinching ass” club—he was a tolerated, incorrigible, narcissistic predator before he died in 2011 at age 88.

Does the thought of Freud trigger a different set of emotions and warrant a more sympathetic evaluation? Was this persona (non) grata proud of his pedigree? He was, after all, the grandson of Dr. Sigmund Freud and could nonchalantly and perversely make such claims as having always adored his grandfather’s earliest, most obscure biological renderings of the microscopic sex organs of an eel. Was Freud thus proud in every way to be a debatable man—truly owning his bad boy charm and cunningly innocent sensibility. Noted in many biographical articles is the fact that he was the damaged son of an overly adoring mother who would sneak into his bedroom and read his trove of poetic love letters whenever she had the chance. Poor Lucian. This is the Freud with an almost criminological form of creativity, as seen in his vapid and uptight, almost nervous, illustrative early portraits of his first wife, Kiti Garman, whose dilated vacant eyes create a disconnect and seem to express the artist’s isolation. This affected style would propel Freud in search of greater depth and realism, to befriend both Giacometti and Bacon, and learn the sacred painter’s ritual of soul excavation, while also apprenticing in the art of excessive drinking and gambling. “I used to go there. Watch him work,” says Freud about Bacon, “And we’d go out. And then he’d drink and everything. And pass out. And then I’d go back and work. It wasn’t very late. Sometime 3 or 4 in the afternoon. And then I’d work for a long time.”

Freud, it would seem, was not bred to be good for good’s sake, but instead cultivated, as he matured, a complex persona: part dandy, part enfant terrible, with selfish intensity—and a Rimbaud-like lust for the big lose or big win. He was the high-stakes allegorical painter, not associated with the shady characters of contraband arms dealing, as was Rimbaud, but with the thug bookies and other desperate types associated with the racetrack, where he transformed his sweet childhood love for horses (and other animals like the whippets he often painted and etched) into a regular fix of adrenaline. According to one tabloid author: “Freud’s betting activities won the misanthropic artist—known for his rampant adultery, violent temper, waitress-groping, poor overall behavior at restaurants, absentee parenting, and paintings of his nude pubescent children—both friends and portrait subjects from diverse social strata.”

So Freud was apparently a restless creative piece of work. Let’s consider the story of a 15-year-old Lucian accidentally burning down his own art school after leaving his first partially smoked cigar smoldering unattended overnight in one of the school’s lofty figure-drawing studios (a detail too good to be true given his aficionado grandpa). In one video interview, Freud reflects, “Maybe it’s because I’m a suppressed pyromaniac, but every time I see flames and sparks, I think HOORAY!”

I can hear the narration of Alex in A Clockwork Orange (played by Malcolm McDowell), leader of a gang of hoodlums, known for his recreational robbery and rape to the symphonic shredding of “Ludwig Van” played on a Moog. Hooray! Indeed.

Freud, who was something of a trust-fund punk, was perfectly frank about the Albrecht Dürer hanging in his living room growing up (a hyperrealistic close-up of tall grasses), while crossing the tracks daily on his bicycle to paint pictures and throw back shots among the working class cockneys of Paddington, where he steadily rose to infamy and immortality.

It would seem that he was initially reacting strongly against Pop, rejecting the trendy, fashionable, decorative aesthetic of the late-1960s. Picture the exotic scenes in A Clockwork Orange that take place in the hip underground of the Chelsea Drugstore, circa 1970, where mod customers can be seen lingering and browsing magazine racks and LPs with pharmacists at the ready to deploy amphetamines and barbiturates to their “flying squad” of gorgeous delivery girls in purple catsuits on scooters. I know what you’re thinking: How could anyone in their right mind reject such an exotic prescription?

Freud, however, seems to have hatched spontaneously as a premature, fully mature artist, with no time to waste on trifles. So he aimed to basically strip his work of artifice. But attitudinally, Freud was not the gleeful thug, “singin’ in the rain,” in a bowler hat and steel-plated jockstrap, while kicking in the entire sinus cavity of some filthy rich art collector (see Kubrick). In his dingy, derelict studio—which looks like a shooting gallery for junkies or some kind of halfway-house for immobilized drunks or even runaway prostitutes looking for a temporary mattress (and supposedly inspired by the caves of Giacometti and Bacon)—Freud was not only sleeping off hangovers. On the contrary, he was advancing incrementally at his own pace and under his own discipline, focusing his eyes, as if to discern the thousand shades of tan in a moth’s wing, while grooming his stiff hogs hair brushes to maintain just the right flex, and penciling in another model. David Hockney once commented, speaking with great fondness on Freud’s cryptovisuality: “He enjoyed looking at somehow … the difference between this and this.”

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Freud’s art of concentration and micro-examination also took stamina and consistency. Not to mention a ruthlessly competitive drive. But mostly, it required the poise to keep telling oneself: There’s no place I’d rather be, nor anything I’d rather be doing. Freud seems to have lived for the thrill of going for broke, of painting that next hypothetical masterpiece: “Unrealistic as it sounds, I want each picture that I’m working on to be the only picture I’m working on … to go a bit further … to be the only picture I’ve ever worked on. … And to go even a bit further … the only picture that anyone has ever done.”

In his standing nude self-portrait, “Painter Working, Reflection” (1993), which is not currently on view at Acquavella but likely to be seen in the fall in London, Freud gives us the old man himself in nothing but a very cruddy pair of work boots, which don’t even have laces and appear to have devolved into a pathetically soft pair of slippers. The boots themselves could be an immersive subject for a Ph.D.—should one compare them to the similar boots by Van Gogh. In one arm, Freud clutches his paint-smeared palette; in the other, a palette knife, as if it were Hamlet’s dagger in his “To be or not to be” monologue. The painting is oozing (literally, I’d imagine) with ontology. There’s a patchwork of glunky, gummy, cruddy flesh tones that convey an anatomy but also a psychology.

Freud would return to the idea again and again that we are all animals, especially once we’ve shed our garments, which in his granddad’s psychoanalytic journals would all fall under the category of desire. What was Lucian to do with such desire? Such id? Such potential for transgression? How was he to ground his multitude of urges? “I hoped that if I concentrated enough the intensity of the scrutiny alone would force life into the pictures.” It would seem that his goal was to use the painting’s time and medium to capture and maybe even constrain his animal instinct. What finally emerged, after decades of painting, was a cast (a company, including himself) of flabby, droopy, naked people passing through their primes with futility and exhaustion.

I wonder what his motley crew of nude humans will look like in the future? Will there be any such thing as aging in the future? Will skin that was once elastic, become plastic? Will i-borgs ever get naked? Will gravity cease to have an effect on our tits and testicles, and earlobes, and chins?

Consider how Freud paints the loose flesh that hangs under his own chin, down into the folds of his neck and clavicles. It’s like a goddamn tent in there—so much flapping skin! Is this the result of his interrogation of the soul, or simply the record of a biological fact?

So much flapping skin! Is this the result of Lucian Freud’s interrogation of the soul, or simply the record of a biological fact?

In another self-portrait, a frazzled looking Freud is seen in profile. We confront a man who is definitely not handsome. I find myself staring with peculiar discontent, as if at myself in the bathroom mirror. I’m reminded of a scene in Crime and Punishment, where Dostoyevsky first describes the ethnic pawnbroker, a few chapters before she is brutally slain. “She was a diminutive, withered up old woman of sixty, with sharp malignant eyes and a sharp little nose. Her colorless, somewhat grizzled hair was thickly smeared with oil, and she wore no kerchief over it. Round her thin long neck, which looked like a hen’s. …”

Maybe Freud paints to get in touch with his inner hen. And to offer his own malignant condition as a gift to the viewer. It’s not an easy present to open. And while some Freud paintings gallop across the finish line second or third (or not at all), despite his rigor building to that convincing, pimply, scarred surface, occasionally one does seem to achieve the primacy he previously described, of feeling like “the only picture that anyone has ever done.”

One such undeniable masterpiece is from 1995, “Benefits Supervisor Sleeping.” This horizontal, life-size, reclining nude woman is nothing less than shocking. But why? The Acquavella show’s guest curator, David Dawson, who was Freud’s longtime studio assistant, wingman, drinking buddy, partner-in-crime, and frequent sitter (apparently, whenever the intended model failed to show up), attempts to tell us, but falls short by titling the show “Monumental.” The show’s press release also beats around the bush in its praise for another of Freud’s accomplishments, his 1990 painting of the performance artist Leigh Bowery, which refers to the man’s “impressive physique.”

Lucian Freud, ‘Naked Man, Back View,’ 1991-92 (The Metropolitan Museum of Art, New York; Purchase, Lila Acheson Wallace Gift, 1993 © The Lucian Freud Archive / Bridgeman Images)

I’ll get to the point—”Benefits Supervisor Sleeping,” depicts Sue Tilley, who, like her friend Leigh Bowery, is shocking because she is spectacularly overweight, or what is properly referred to as morbidly obese—fat. I see it as similar to the way the comedian Amy Schumer puts it in one of her hilarious, self-deprecating standup routines (on Netflix), where she riffs on both being pregnant as well as being the kind of woman to let it all hang out, and thus become perpetual fodder for the insult-slinging fat-shamers of the world. On being five-months pregnant, she says that when gossipers asked, “Is she showing?” the reply was: “No more than normal. Just looks like she took her Spanx off.”

Fat apparently is still a terrible word and is therefore still a big-money form of funny. Not to sound like I’m doing some kind of George Carlin shtick, but while questioning what makes this painting more than average, I conclude that the answer is not in anyone’s “monumentality” or “impressive physique.” It is simply in Freud’s audacious portrayal of an overweight woman.

And this makes it arguably the rudest nude since Manet’s 1856 “Olympia (a reclining prostitute in black choker considering the painter’s implied offer), and Courbet’s 1886 in-your-face “L’Origine du monde” (a notoriously obscene midsection of a reclining woman with legs spread).

Freud’s alchemy of brute nudity, his contribution to the vulgarity and violence of the modern woman, is, on one hand, like the roguish Courbet, with offensive manners and a surface that could almost be described as having acne (a palpable granular density beyond impasto achieved due to his insistence on using Cremnitz, the lead-based paint that was recalled in the mid-1970s). But he is also like Manet, in suggesting that erotic and explicit power lies not merely on the surface, but in the premise, as the pictorial text fuels a debate had by anyone unwilling to wait any longer to topple the ingrained sexist gaze and its contribution to the objectification of women in all beauty industries (art, philosophy, poetry, prostitution, fashion, cosmetics, etc.).

So, is Sue Tilley (aka “Big Sue”) the brunt of a jokester at a smoker? Is she more shocking because she’s more woman? Or, despite her monumental measurements, is she in fact less woman? Is she, in other words, even further degraded than a reclining 19th-century prostitute or a scandalous bohemian redhead mistress (Courbet’s model is fabled to have been Joanna Hiffernan, just in case you’re curious)? And, is she even more compelling because she continues to descend (as Duchamp implies in his famous nude) the proverbial “staircase” of idealized beauty, to be debased, and thus released, in a way, from Platonic perfection, and set free to be a real, rationalizing individual, just like a man. My point then is: Freud generously let this woman out of the manacles of the male gaze.

Clearly, Sleeping Beauty was, and still is, a wake-up call. The same way Lena Dunham woke us up with her acute linguistics and frankness to accept the unacceptable woman. Likewise, she is thus not a scandal for what she is, but for what she is not. Sue and her co-conspirator Lucian teamed up to give art a monumental middle finger. The yucky sofa only barely seems to support her. We can feel its old springs being crushed. We fear that the weak antique might even buckle. Instead of ‘Nude Descending the Staircase,’ this painting could be titled, ‘Nude Collapsing the Staircase.’

All kidding aside, the ‘Benefits Supervisor’ seems to be near the tipping point—as if she could tilt right out of the shallow picture plane that she occupies, like in John Singer Sargent’s famous “Lady Carl Meyer and her Children” (1896), a painting that weirded out critics back in the day simply for accurately capturing the skewed angle that a standing painter sees peering down on his seated model. Freud, like Sargent (a voyeur if there ever was one) hovers somewhere in the ether. But it is the invisible gravitational force that becomes the star of the picture—gravity comes, in other words, to consume everything like a monster in a horror film. The lead Cremnitz starts to seem like tar. And this effect triggers, perhaps subconsciously, the viewers anxiety, until we begin to feel trapped by our own bodies, held down by our own weight and ultimately stalked by our own mortality.

I’m reminded, for a brief second, of John Waters’ drag queen movie star, Harris Glenn Milstead, aka Divine, who died in 1988. But her excessive trashiness was so much more ironic and fabulous—so much more camp. Divine wanted to be judged, she wanted to be monumentalized. But Freud has not sent up a cultural balloon of cheap air; he has taken us, via paint, to the bottom, to the pit, to perceive and feel the dead weight of our existence. He once said: “When someone is naked there is in effect nothing to be hidden. Not everyone wants to be that honest about themselves, that means I feel an obligation to be equally honest in how I represent them. It is a matter of responsibility, in a way I don’t want the painting to come from me, I want it to come from them. It can be extraordinary how much you can learn from someone by looking very carefully at them without judgement.”

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