Sometime on Tuesday, November 8, 1960, a 66-year-old widower and self-described “moderate Republican” went to his polling place in Stockbridge, Massachusetts, to vote for his state’s junior senator for president. Never the most forthcoming of men, Norman Rockwell hadn’t told his family he was backing John F. Kennedy. He’d painted portraits of both candidates for the Saturday Evening Post, and he just didn’t like Richard Nixon’s face.

It was only a short walk down Main Street from the two-story Colonial house supposedly once occupied by Aaron Burr, whose derelict red barn Rockwell had converted into his fastidiously tidy studio. He’d called Stockbridge home since relocating from rural Vermont six years earlier, mainly for proximity to its renowned Austen Riggs psychiatric center. His second wife, Mary, who struggled with alcoholism and depression, had been a chronic patient there.

In those newly cosmopolitan times — the Mad Men era, for shorthand’s sake — the Anytown, USA, that Rockwell had depicted on hundreds of Post covers was becoming a curio at best and an object of derision at worst. Nixon still espoused a mealy-mouthed fealty to those pseudo-Rockwellian virtues. By choosing Kennedy instead, Rockwell might as well have been casting a ballot to hasten his own obsolescence. But nobody could disagree that he’d had a good run.

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Born in 1894 on Manhattan’s Upper West Side, Rockwell had never shown interest in any other career besides commercial illustration. Before his 16th birthday, he had dropped out of high school to enroll at New York’s Art Students League. Untempted by the bohemia of Greenwich Village and seemingly indifferent to (or unnerved by) the concept of a love life, he had business cards printed for himself while he was still in his teens.

Most midcentury Americans would have had trouble fathoming the idea that Norman Rockwell had ever been that young or unknown. In the four and a half decades since his Post debut in 1916, his humorous vignettes of awkward situations and glowing ones of social and domestic rituals had defined the nation’s most idyllic self-image. From Andy Hardy movies to Frank Capra’s It’s a Wonderful Life, Hollywood’s version of homey American verities was by and large a facsimile of Rockwell’s.

But by the time he cast that vote in 1960, his perspective was growing increasingly remote from the bulk of his fellow citizens’ lived experience in cities and postwar suburbs. The concept of kitsch had begun following Rockwell around in print like one of the lovelorn puppies he would include in a painting whenever he was at a loss for an effect (a habit that he would later mock).

Worse, the Saturday Evening Post wasn’t the national arbiter it had been. A few months after JFK’s inaugural, the magazine would promise jittery advertisers a drastically modernized look under a new editor-in-chief who promptly recanted the Post’s endorsement of Nixon the previous fall. The demotion of Rockwell’s Main Street America to the Rat Pack’s Nowheresville wasn’t explicit, but everybody got the gist.

It’s unlikely he even considered retiring. At ease only when at his easel, he took little interest in hobbies — or even in his family. Not the most well-rounded of men, Rockwell, when asked to describe his leisure activities by Edward R. Murrow on CBS’s Person to Person in 1959, responded that he couldn’t think of any, except the “countless hours” he spent tearing up diaper cloths for use as paint rags.

In any case, he was obviously too sedate to change his spots, no matter how speedily the country around him was changing. That would have been most people’s guess, at least.

It would have been spectacularly wrong. The tumultuous ’60s would convert Rockwell into an overt social liberal — and the era’s unlikeliest practitioner of polemical art.

Even the Norman Rockwell Museum can’t make sense of his late-life political transformation. Amid the familiar Rockwelliana on display there is 1964’s The Problem We All Live With — which his biographer Deborah Solomon, in her 2013 book, American Mirror, calls “the most famous painting of the civil-rights movement”— as jarring as it must have been in the pages of Look magazine more than 50 years ago. But it was only the first of his 1960s paintings to upend everything “Norman Rockwell” stood for.

Indeed, one of the minor marvels of the ’60s was that the period made Rockwell happier than he’d ever been. The hippies he came to dote on had a word for it: liberation.

After Mary died unexpectedly of coronary heart disease in August 1959, her husband’s vestigial social life centered on a Stockbridge men’s club called the Marching and Chowder Society. Its members met once a week to chew over the news of the day, from the nuclear arms race to the South’s roiling battles over desegregation.

Up until then, the average lamppost had taken a livelier interest in current events than Rockwell did. His only concessions to topical urgency had come between Pearl Harbor and Hiroshima. Besides proselytizing for democracy with his epic Four Freedoms series (a quartet of paintings depicting freedom of speech and worship as well as freedom from fear and want — the last of these featuring his celebrated image of a family’s Thanksgiving feast), he’d regaled Post readers with covers featuring a regally posed Rosie the Riveter and a youthful soldier’s homecoming. But then he’d gone back to his familiar tableaux, seemingly unaffected by Elvis Presley, suburbia’s advent, or the Cold War — and certainly not by Brown v. Board of Education, Rosa Parks, or Little Rock.

Rockwell had every reason to feel personally un-implicated in the country’s burgeoning racial strife. There’s no record of him encountering black-white tensions during his youth in New York City and New Rochelle, nor, later on, in relatively isolated (and white) Vermont or Stockbridge. As for his Saturday Evening Post America, it could have been what Ronald Reagan had in mind when he notoriously reminisced about the days “when we didn’t even know we had a racial problem” — a “we” as defining, if far more damning, than the one in The Problem We All Live With’s title.

The Post banned illustrations showing African Americans in anything other than menial roles. Rockwell had generally been docile about that. Very little in his Post work had prepared his audience for how unambiguously and provocatively he declared himself on the subject of desegregation in his Look magazine debut.

At the time, most white Americans still thought of racial injustice as a “problem” only Southerners wrestled with. The contest between Kennedy and Nixon ran its course without civil rights being much of an issue, with one dramatic exception. In October 1960, a month before the election, Martin Luther King Jr. was jailed after leading an Atlanta sit-in. In a surprise move, JFK’s brother Robert F. Kennedy publicly intervened to help secure his release. The Kennedy family’s actions — while Nixon cautiously kept mum — would abruptly change the equation. African American voters significantly bolstered JFK’s razor-thin margin of victory.

Rockwell’s only involvement in the 1960 election, aside from voting, had been his portraits of Kennedy and Nixon. His son Peter (one of the three he had with Mary) remembered Rockwell grousing that “the problem with doing Nixon is that if you make him look nice, he doesn’t look like Nixon anymore.” As the magazine’s preferred candidate, Nixon got the cover dated closer to Election Day, not that it did him any good.

Never fond of television, Rockwell probably went to bed without watching the evening news on November 14, 1960, just under a week after Kennedy’s victory. If so, he wouldn’t only have missed the sight of a knackered Nixon shaking hands with the new president-elect in Key Biscayne, Florida. He’d also have missed a mob of white New Orleanians howling abuse as they witnessed the unthinkable: a quartet of US marshals escorting a 6-year-old girl named Ruby Bridges as she entered school to attend first grade.

Bridges was one of just four African American first-graders who’d been chosen to integrate the city’s school system. But at least Leona Tate, Tessie Prevost, and Gail Etienne got to enter McDonogh 19 school as a trio. Bridges, flanked by the marshals, went up the steps of William Frantz Elementary School on her own.

Not that anybody knew her name. To readers and viewers of most news outlets, she was simply “the little Negro girl,” and so she remained until the 1990s, when the adult Bridges was reunited at a Black History Month event in New Orleans with one of her real-life escorts — and the painting.

What drew Rockwell to the subject three years after the fact? His interest may have been sparked by the writings of psychiatrist Robert Coles, who’d met with and counseled Bridges and her family. The artist may have read John Steinbeck’s 1962 bestseller Travels With Charley, whose concluding chapter contains his eyewitness account of the havoc outside the school on a typical day in the autumn of 1960. One passage, in particular, vividly anticipates the central figure in Rockwell’s painting: a glimpse of “the littlest Negro girl you ever saw, dressed in shining starchy white, with new white shoes on feet so little they were almost round. Her face and little legs were very black against the white.”

Yet Rockwell unmistakably had Ruby Bridges’s ordeal on his mind before either Coles or Steinbeck weighed in. His most ambitious painting of 1961 was The Golden Rule, which featured more than two dozen people of all races and faiths illustrating the caption “Do unto others as you would have them do unto you.” Two of them are African American: a man in a pointedly middle-class white shirt and tie as well as a neatly dressed girl prominently placed in the foreground. In an early version of The Golden Rule, which is the one propped today in the artist’s studio at the Rockwell Museum in Stockbridge, the girl’s hands are simply clasped in prayer. In the final painting, they’re clutching two schoolbooks.

Not many Post subscribers in 1961 were likely to miss the allusion to the child who’d gotten so much news coverage the previous autumn. Segregationists certainly didn’t; they sent Rockwell the only hate mail he’d received in his 45-year career. But his relationship with the Post had been deteriorating in any case. Its editors had concluded that his brand of folksy humanism was passé. They also seemed uninterested, as The Golden Rule hinted, that their former mainstay had a burgeoning interest in more provocative social themes. That summer, the new regime unveiled its plans for a revamped Post, including “art work ... considerably more abstract than anything that has appeared in the magazine.” Rockwell’s sardonic response was his very funny January 1962 cover, The Connoisseur, depicting a stocky gent in banker’s gray pondering a Jackson Pollock riot of splattered red, yellow, and blue.

His imitation Pollock was expert enough to delight the artist Willem de Kooning. But The Connoisseur proved to be the last of his great Post covers. Just five months after it was published, Rockwell got new marching orders, and they rankled. He was to be confined from then on to producing portraits of statesmen, plus the occasional celebrity.

Terrified of ending his relationship with the Post, he tried to oblige his bosses. But in May 1963, he scrawled a remarkably agonized 3 am lament: “All of this debasement, depression, unsatisfaction. Isn’t this the answer — if necessary, die doing something worthwhile. A worthy end ... not humiliating fear and groveling. Have I got the sustaining courage to cut it through? Cut the knot myself not die groveling.”

Four months later, he wrote the Post’s latest art director that he’d “come to the conviction that the work I now want to do no longer fits into the Post scheme.”

His major emotional sustenance during this period came from his new wife. Fourteen months after Mary died, after a brief acquaintance, he married Molly Punderson, a 64-year-old schoolteacher who, as biographer Solomon puts it, was “not known to have had any male suitors” before they wed. But Rockwell’s marital needs had never been primarily sexual, and he knew what he could count on from her: “You will help, be with me, admire me,” he addressed Molly in that same insomniac cri de coeur. “I have the courage with you.”

Rockwell’s final Post cover, for the memorial issue commemorating John F. Kennedy’s assassination, that November, was a reprint of the artist’s 1960 JFK portrait. But by then, he’d already signed up with Look. The rival to Henry Luce’s Life magazine, the more politically adventurous Look had no misgivings about the unlikely image Rockwell proposed as his debut, despite how it diverged from everything he was famous for — unless, of course, that was part of its appeal. On October 1, 1963, art director Allen Hurlburt wrote him, “As you know, Dan [Mich, Look’s editor] and I are very excited about your idea for a painting of the Negro girl and the marshals. ... In checking our production schedules I find that we should have the art work by November 10 to make an early January issue.”

Rockwell told Hurlburt he’d gotten a head start on the painting, having identified a willing model: “I already have the 7 yr old little girl and she is perfect. Her grandmother is sewing the white dress for her. ... Be assured I am very excited about the picture.” Excited wasn’t a word he’d often used about his assignments for the Post.

Rockwell’s search for the “perfect” little girl may seem odd, given the common belief that Problem simply replicates a news photograph. But that misconception is an unwitting tribute to how completely the real episode and Rockwell’s depiction of it have fused in our collective memory. Aside from the basic situation, virtually every detail of the picture is Rockwell’s invention.

His usual MO was to sketch or paint from photographs of local residents, who would come to his studio and then follow his directions as they struck various poses. He’d employed a photographer named Bill Scovill virtually full-time since 1953, and it was Scovill who likely took the reference photos for The Problem We All Live With.

Only two African American families lived in Stockbridge then. Rockwell was friendly with the patriarch of one of them: Bill Gunn, who’d posed for The Golden Rule and also chaired the Berkshire County chapter of the NAACP. Rockwell became a lifetime member in October 1963, around the time he began working on The Problem We All Live With.

Two of Gunn’s granddaughters were approximately the right age to stand in for Bridges: first cousins named Lynda and Anita Gunn. Lynda ended up doing most of the posing. Anita and other members of the Gunn family, who had been invited to observe the photo sessions, enjoyed the Coca-Colas that Rockwell passed around. For Lynda, the tricky part was balancing herself on two wooden boards — front foot tilting upward, back foot tilting down — to simulate walking. It was an old device of Rockwell’s, and he also used it for the separate reference shots of her four adult escorts.

At least two of the burly men who posed for the painting were authentic US marshals sent out from Boston to oblige him. Another was Stockbridge Police Chief William J. Obanhein, who, oddly enough, would later enjoy a peculiarly ’60s-ish fame of his own as the “Officer Obie” of Arlo Guthrie’s 1967 hit song “Alice’s Restaurant.”

But we’ll never know which of Bridges’s escorts he impersonated. In one of Rockwell’s boldest breaks with representational convention, the marshals are painted from their shoulders down — not just faceless but headless. While that doesn’t dehumanize them, exactly — if anything, it makes their determined bearing more eloquent — nothing could better emphasize Rockwell’s understanding that the moment’s emotional truth lay in Ruby Bridges’s solitude. “Of course they were terribly disappointed that I didn’t show their faces,” he would explain years later. “But if I’d shown the four faces, you wouldn’t have seen the little girl.”

Rockwell’s depiction of Bridges was another matter. He chose to darken her skin tone, making it darker, in fact, than that of either Lynda or Anita Gunn. Today, such artistic license — deliberately darkening a subject’s appearance as a way of overemphasizing race and provoking the viewer — would be seen as racially insensitive. But he plainly hoped to disconcert Look’s readers by making her blackness the picture’s central issue. Paradoxically, that also made her unmistakable individuality more arresting.

Except for the somewhat too-vivid yellow of the marshals’ armbands — arguably, the picture’s only flaw — and the almost bridal whiteness of the little girl’s dress, which is one of its masterstrokes, the only patch of color that’s meant to draw the eye is the stain on the wall behind them, the residue of a flung tomato. (“It took me ten tomatoes to look as though it had really splashed,” Rockwell later recalled.) But it’s not as prominent as Problem’s most shocking ingredient today: the all-caps racial slur scrawled on the wall.

With its decapitated marshals and the diminutive Ruby walking in stark profile, the painting is among Rockwell’s most stylized. There is even an artificiality to the way the four bodyguards’ left arms are cocked back so that the viewer can see their badges as well as the court order tucked into the lead marshal’s side jacket pocket. The artist has pared down the actual event to its essential meaning — an atypical treatment for Rockwell, who loved to pack his canvases with incidental detail.

What’s strikingly absent, except by unpleasant implication, is Rockwell’s most durable theme: community. The mob heckling Ruby Bridges is nowhere to be seen, and only gradually does it sink in that it’s because we’re looking at Bridges and her escorts from the mob’s point of view. We can only dissociate ourselves from them by refusing complicity.

When the Look issue came out, Rockwell was in Moscow, which would have confirmed white bigots’ worst suspicions even — or especially — if they’d known he was participating in a cultural exchange program at the US Information Agency’s behest. He didn’t return home until early February, entirely unaware of how The Problem We All Live With had been received.

According to Solomon, he was greeted by “sacks of disapproving mail” from readers that Look’s editors had forwarded to him. The negative letters were venomous: “Anybody who advocates, aids or abets the vicious crime of racial integration is nothing short of a traitor to the white race, and a traitor to the illustrious white founders of this country,” wrote G.L. Le Bon of New Orleans. “THE WAR HAS JUST BEGUN!”

But there were supportive letters, too. Chester Martin of Chattanooga, Tennessee, wrote, “I have never been so deeply moved by any picture. ... Thank you for showing this white Southerner how ridiculous he looks. The truth is pretty hard to take until we get it from a Norman Rockwell.” Onetime Negro League third baseman turned real estate broker and occasional poet David J. Malarcher was stirred enough to send Look a poem he’d written in honor of the illustration, including these verses: “Their hands are tense / Their gait is rare / Their arms are ready for the fray / The little girl is unaware / That she is history today.”

Another approving letter came from a self-described former Rockwell “debunker” who’d once scoffed at “how maudlin and commercial” his work was. “Permit me now to choke on my words. ... YOU have just said in one painting what people cannot say in a lifetime.” In his thank-you letter, Rockwell modestly explained that “I am [sic] just had my seventieth birthday and I am trying to be a bit more adult in my work.”

“Adult” is an interesting choice of words for a man his age. When Mary was alive, Rockwell had plunged into therapy, almost as if he couldn’t stand the idea of Mary monopolizing the shrinks’ attention. He had sessions twice a week with Erik Erikson, the analyst to whom we owe the locution “identity crisis.” Erikson was famous mainly for his work with troubled children, and the most beloved illustrator in American magazine history occasionally resembled one. The side of Rockwell that had never matured left him uncommonly dependent on validation from others, maybe now more than ever.

As a result, Hurlburt’s encouragement thrilled him. Besides offering specific recommendations that Rockwell happily accepted — it was Hurlburt who suggested the marshals be depicted with their arms back — he provided the support and approval Rockwell craved. “I don’t want to sound slushy or sentimental,” he wrote Hurlburt in the spring of 1966, “but I can’t resist writing you to tell you how much your creative art direction has meant to me. You have given me the opportunity over and over again to paint pictures of contemporary subjects that I am fascinated with.”

The most unsparing picture he ever painted was the accompanying illustration for a 1965 Look article called “Southern Justice.” As unknown today as Problem is famous, Murder in Mississippi was Rockwell’s depiction of the June 21, 1964, killing of civil rights workers Mickey Schwerner, Andrew Goodman, and James Chaney — two white New Yorkers and a local African American volunteer — by Klansmen and local police. Spooky, harshly lit, and almost barren, it’s as close as Rockwell ever came to Goya’s Los Desastres de la Guerra.

Because the exact circumstances under which the three men died weren’t known, Rockwell struggled with deciding how to portray their final moments, initially including their killers in the frame before reducing them to looming shadows. What stays constant is his depiction of the victims: one dead, one dying, one grimly preparing to meet his fate.

Sprawled on the ground, Goodman has already been killed. Schwerner is still standing, his head turned in profile to gaze at his executioners. Linking the two white men is Chaney, who’s been shot once and is on his knees, clutching Schwerner with both hands for support. Schwerner’s right hand has pulled him close in an embrace, tugging up Chaney’s T-shirt to expose his bare back, Rockwell’s way of emphasizing both Chaney’s race and his vulnerability.

Rockwell’s unusually detailed notes on the murders are a moving testimony to his determination to do right by the civil rights workers. He remarked on Goodman and Schwerner’s “beatnik sneakers and blue jeans.” In one poignant observation, he wrote that “they had, all three, had haircuts the day before.” The reference photos also emphasize his emotional commitment. His son Jarvis modeled as Schwerner, and Rockwell himself posed for a detail photo of Chaney’s bloodied hand gripping Schwerner’s bicep. Both the hand and the bicep are Rockwell’s.

It could be the most strangely haunting picture of Norman Rockwell anybody ever took. Because his facial expression doesn’t matter, he’s gazing placidly at the camera, wearing a slight smile. Yet, consciously or not, by impersonating Schwerner and Chaney simultaneously, he’s claiming an identification with both victims — one black, one white.

“I tried in a big way to make an angry painting,” he wrote to Hurlburt in May 1965. “If I just had a bit of Ben Shahn in me it would have helped.” It’s an interesting wish, since the very left-wing Shahn’s Depression-era paintings had derived their force from semi-grotesque distortions that were utterly at odds with Rockwell’s innate naturalism. As it happened, Hurlburt apparently agreed; Look opted to print not Rockwell’s final version of the scene but one of his rawer preliminary studies. Only 18 months into their association, this was the acid test of Rockwell’s trust in his new patrons. Initially disgruntled, he ended up conceding that “All the anger that was in the sketch had gone out of” the finished painting.

Look would never print a Rockwell picture that angry again.

During the next five years, Rockwell’s paintings on “contemporary subjects” for Look were hardly confined to indictments. He’d simply gotten more selective in the aspects of modern America he found worth celebrating. He painted more than one picture championing the Peace Corps: “I love ... the ideals and the performances of these young people,” he told Hurlburt. He boosted Lyndon Johnson’s war on poverty. Maybe most endearingly, he was besotted with NASA, producing gadget-happy depictions of the space program.

Even the third and last of his major civil rights paintings for Look struck a relatively hopeful note, amounting to a reconciliation of the “Norman Rockwell” of yore with his new focus on topicality. New Kids in the Neighborhood featured a pair of black children and a trio of white ones sizing each other up as a moving van is unloaded behind them. The benign mood is undercut only by a detail that isn’t easy to spot even face-to-face with the original and that must have been indiscernible in Look’s reduced reproduction: a white woman peering from a nearby window, her expression conveying worry, verging on hostility.

Rockwell hardly wanted New Kids in the Neighborhood to be his last word on the subject. But he and Look were unable to agree on the much grimmer painting he proposed next. Existing in multiple versions, none of which seems to be fully finished, Blood Brothers depicts two men — one black, one white — dying side by side in a pool of their intermingled blood. The point, of course, is that you can’t tell whose blood is whose.

Initially, Rockwell wanted to set Blood Brothers in “the ghetto,” in the parlance of the era. But Look urged him to transpose the scene to Vietnam, which would obviously have implied a different set of pieties. Rockwell gave the revision a dutiful try. By late 1968, however, he was grumbling, “I think I want to go back to the ghetto.”

Either because of that impasse or some other dispute, he and Hurlburt eventually abandoned the idea. But if the combat zone version of Blood Brothers had seen print, it would have been Rockwell’s only painting for Look to deal with the Vietnam War head-on. He may have balked because the concept left his personal position on the war unstated, and he and his wife, Molly, were both staunch in their opposition to it.

As citizens, he and Molly weren’t shy about letting Lyndon Johnson know where they stood. An uncooperative sitter when Rockwell had painted the new president in 1964, LBJ likely grew weary of the stream of telegrams from the couple demanding negotiations instead of bombing. But a Rockwell artwork directly attacking the war would have been too polarizing for Look’s editors, and it appears he never proposed one.

What he could do was agree to paint philosopher and peace activist Bertrand Russell’s portrait for the very left-leaning Ramparts in 1967. Almost a quarter-century after tackling the Four Freedoms for the Pentagon’s Office of War Information, he firmly refused a Marine Corps request to produce a propaganda poster. “I was supposed to do a portrait of a soldier in Vietnam kneeling over to help a wounded villager and love shining in their eyes,” Rockwell told Women’s Wear Daily in 1968. “I thought about it a lot, and my wife said, ‘You can’t do that and you know you can’t.’ [So] I’m doing John Glenn instead.” The first American astronaut to orbit Earth was the kind of Marine Rockwell had no problem lionizing.

By the late ’60s, he often heard from older fans who wondered why he couldn’t go on giving them “those sweet old pictures like you used to do.” But Rockwell was unmoved. “You can’t make the good old days come back just by painting pictures of them,” he snorted. “That kind of stuff is dead now and I think it’s about time,” he told another interviewer.

After a lifetime of diffidence, Rockwell’s interviews from the end of the decade are remarkably energetic and cocky, militant, even. Without disavowing his earlier work — “I couldn’t have had my tongue in my cheek for 50 years” — he never stopped insisting that “red-cheeked little boys and mongrel dogs” no longer typified America. “Now it’s all sex or race troubles,” he remarked, “homosexuality or college riots, and I think it’s a great challenge.” Even more startlingly, he declared in that pivotal year of protest, 1968, that he “couldn’t paint the Four Freedoms now. I just don’t believe in it.”

A different kind of freedom entranced him instead. Rockwell was enamored of the counterculture, not least for its visual éclat. “I think the hippies and the Yippies are wonderful,” he told the International Herald-Tribune. “I think of everybody as models, and I’m so goddamned sick of business suits with conventional haircuts, like I have.” In 1968, Rockwell pointedly included a hippie couple — he in a fringed jacket, she with a flower in her hair — among the concerned citizens in The Right to Know, his last “political” painting, which shows a multicultural cross-section of Americans staring accusingly at an empty leather chair. (The caption’s mention of “wars we do not want” finally made his position on Vietnam explicit.) Touchingly, among the faces — all dramatically underlit — is the artist himself, his hand tenderly resting on the young woman’s arm.

Rockwell desperately wanted to paint beat poet Allen Ginsberg as well as Bob Dylan and his family. While nothing came of either project, Rockwell did paint two of Dylan’s onetime sidemen when he agreed to do the cover art for guitarist Mike Bloomfield and organist Al Kooper’s album The Live Adventures of Mike Bloomfield and Al Kooper. It’s one of his most carefree paintings, showing Bloomfield “smoldering through ice-blue irises” and looking “more sensual than any other man Rockwell ever painted,” as Vanity Fair’s David Kamp noted in a 2010 essay.

Nonetheless, Look expected Rockwell to do his due diligence in election years, even if his enthusiasms lay elsewhere. Tasked with painting the 1968 presidential candidates — Gene McCarthy, Bobby Kennedy, and Hubert Humphrey among the Democrats; Nixon and New York Gov. Nelson Rockefeller among the Republicans — he chose to render all of them with two faces: the Rockwellized version of Greek masks of comedy and tragedy. (He wanted to paint independent segregationist candidate George Wallace in front of a funereally black background, but Look vetoed that one.)

As had been the case in 1960, the eventual Republican nominee — “the hardest man I had to paint, ever” — was a challenge. “[Nixon’s] got a mean eye,” he said. “And then he has these big chestnuts in his jowls.” That August, with the Republican convention done and the Democrats’ debacle in Chicago looming, Rockwell wrote to Hurlburt, “I was delighted to have you call me yesterday and tell me that I don’t have to paint Mr. Nixon again.”

But he did. Once Nixon won, Rockwell had to paint him as “Mr. President.” It’s now the only Rockwell painting in the National Portrait Gallery, and this time around, he managed what he’d once said was impossible. His subject looks like a nice man who is, nonetheless, unmistakably Richard Nixon. At any rate, Rockwell — as no one else did — captured Nixon’s eternal, tentative, thwarted wish to be the good-hearted person he wasn’t, which is the painting’s peculiar beauty.

Despite his aversion to the new president as a subject for portraiture, Rockwell had voted for him this time around. Whatever prompted his choice — loss of heart, alienation from the Democratic Party’s 1968 shambles, or credulous hope that Nixon might actually end the war in Vietnam — it was a wan coda to the most dramatic and exhilarated (indeed, the only) self-reinvention of his long career.

Largely sidelined after 1972 as he developed dementia, eventually dying in 1978 at age 84, Rockwell never painted another significant picture again.

Tom Carson is a National Magazine Award-winning writer whose work has appeared in Esquire, GQ, the New York Times, the Village Voice, Rolling Stone, and other publications.