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How Muhammad Ali's Iconic 'Esquire' Cover Helped Cement a Legend

George Lois, the magazine's former art director and longtime friend of Ali, recalls influence and legacy of "a true superhero"

George Lois, former Esquire art director and longtime friend of Muhammad Ali, details the creation of the boxer's iconic magazine cover. Credit: Thos Robinson / Getty

In early 1968, Muhammad Ali was suffering the slings and arrows of outrageous fortune. Stripped of his heavyweight title and banned from boxing because he refused to be inducted into the U.S. military due to his opposition to the Vietnam War, the world's most famous athlete was smeared as a draft-dodger and was battling to stay out of prison. (It would be three years until the Supreme Court heard his case.) Plus, his 1964 conversion to Islam, which prompted him to change his name from Cassius Clay to Muhammad Ali, drew additional ire during a time when the Civil Rights movement roiled America. So when Esquire art director George Lois began thinking of how best to portray the embattled boxer on the magazine's cover, which would become one of the most famous of the 1960s, he hit upon the idea of having his subject be struck by actual arrows.

"Back in those days, there was no Wikipedia or Google, so I did some research on Saint Sebastian," Lois tells Rolling Stone after Ali's death on Friday. An iconic third-century Christian martyr who was slain with arrows for his faith, Sebastian (and his violent death) was a popular subject for artists. As Lois recalls, "There were many, many paintings of him, and I was trying to find one where his body was solid and strong, but his arms were behind his back and he was in pain."

When Ali arrived at the studio for the shoot, Lois (who is widely recognized as an inspiration for Mad Men's brilliant creative director Don Draper) showed him a postcard of a painting of Sebastian rendered by 15th-century artist Francesco Botticini. Ali loved the connection between Sebastian's persecution and his own until he recognized a major problem, telling Lois, "I can't pose as a Christian. It's against my religion."

"I said, 'Oh, shit,'" Lois remembers. "I've got a studio [full of] people — they can see I'm gonna lose the shot." As a last-ditch measure to save his idea, Lois asked to speak to Elijah Muhammad, the leader of the Nation of Islam and Ali's spiritual guide. "Elijah Muhammad and I had [a phone call] — maybe it was three minutes, but it felt like 20 minutes," says Lois. "He wanted to know who I was, how old I was, am I religious. We talked about symbolism and martyrdom. He knew full well why I was doing it. Finally, he said, 'I think it would be a very good image.'"

Satisfied, Ali posed for the photo while Lois's team attached six arrows to his body to mimic the Botticini painting. The champ quickly internalized the martyr conceit. Lois remembers that during the shoot, "Ali said, 'Hey, George…,' which always meant he wanted to talk. He took his right hand out from behind his back and pointed at each of the arrows. And then he'd say the names of the people in this world that were out to get him. He'd point to one arrow: 'Lyndon Johnson.' The next one: 'General [William] Westmoreland [who led the Vietnam operation].' Then: 'Robert McNamara.' Each of the arrows [was] a person in the government that had hurt him. I can't even tell you how stunning it was."

"He was a true superhero of American history."

The art director had first met the boxer in the late 1950s before Ali (then Clay) departed for Rome for the 1960 Summer Olympics, where he'd win gold. Even then, the fighter's larger-than-life persona was becoming legendary. Lois recalls a story he'd been told: "In his first fight, when I think he was 13, he predicted he was gonna knock out the kid he was fighting. When he was 13!"

When Clay visited New York, he took a bus from his hometown of Louisville. (He was scared of flying.) Lois, who's almost 11 years older than the pugilist, said that the young man absorbed lessons during his time in the Big Apple that would inform his future celebrity. One day, the fighter trekked to the nightclub of one of his idols, the boxer Sugar Ray Robinson. "Sugar Ray showed up, and [Ali] stops Sugar Ray to say, 'Mr. Robinson, my name is Cassius Clay. I'm a boxer.' And Sugar fuckin' just brushed him away and walked past him. Later, he told me, 'That's when I knew that when I became famous, I was gonna treat everyone good, everyone wonderful.' And he did."

His voice occasionally breaking while reminiscing about his friend — "It's hard to talk about him, y'know, because he was a wonderful man" — Lois doesn't speak of Ali as an athlete so much as the principled, funny friend he knew for more than 50 years. "He was an incredible human being," Lois says. "And one of the great Americans of all time. He was a true superhero of American history. And he was a worldwide ambassador of courage and conviction."

Over an hour-long interview, Lois, who turns 85 later this month, tells many stories of his time with Ali, often imitating the champ's swaggering speaking style. How Ali helped Lois organize events in the mid-1970s to raise awareness for the unjust 1967 incarceration of boxer Rubin "Hurricane" Carter. But also how he could be perplexing: Ali spoke out against the repression of African-Americans, but his favorite singer was Elvis Presley. This baffled Lois: "I said to him, 'Y'know, Elvis gets all that credit, but he really derived a lot of [his stardom] from black music.' And he said, 'Yeeeeah, but he's still Elvis!'"

Still, Ali was happy to see his bravado and dazzling wordplay influencing younger African-American musicians. "We were driving in a convertible," Lois says, "and Bronx rap music was playing [in the car]. The song finishes, and I said, 'You know, Muhammad, that rap — that's you. They're taking that [flow] from you — that's what you do.' He said, 'Yeeeeah, George, you don't understand: [rapping] First, I rap them with my mouth — then I rap them in the mouth.' That was how quick he was."

"I said, 'You know, Muhammad, that rap — that's you. They're taking that [flow] from you."

Lois's last meaningful conversation with the champ was about four years ago. According to Lois, during that encounter, "he could still talk clearly" despite being diagnosed with Parkinson's Disease in 1984. "He spent an hour-and-a-half — because he knew I was a nonbeliever — reading from the Bible and the Koran. And he'd always say, 'George, never eat poke'" — slang for pork — "and I'd always lick my fingers and say, 'Oh, I love poke.'" The memory makes Lois laugh, but later in the interview, he confesses sadly, "It was very difficult … that twinkle in his eyes — the last four or five years, he didn't have anything in his eyes. They were dead. The Parkinson's was really eating him up alive."

Talk returns to that classic 1968 Esquire cover. Even as the shot was coming together, Lois knew it would be timeless. ("Everybody in the place had their mouth wide open when they saw it," Lois says.) Its impact went far beyond being an indelible photograph, though. Lois points to the image as the moment that galvanized Martin Luther King, Jr., who hadn't yet explicitly spoken out against the Vietnam War, to finally denounce the conflict.

But the cultural ripples continued for decades. Lois remembers serving on a jury "20 or 30 years ago" — when the court case ended, the judge invited the jury members to join him in his chambers. "The judge said, 'The reason I wanted you to all be here is that there's a man in this room who shaped my life. His name is George Lois, Juror No. 4.' He described how he saw that cover when he was at Columbia University and how there were debates over it and screaming arguments about it during the goddamn Vietnam War. He said, 'That cover changed my politics and changed my life.' I've gotten people saying things like that to me. That's beyond iconic."

But for Lois, that magazine cover's imprint is as much personal as it is political, forever connecting him to a man he loved. Around 2003, when Lois was releasing a memoir entitled $ellebrity, which featured Ali on the cover, Vanity Fair wanted to stage a photo between Lois and the champ. Lois traveled to Ali's home in Michigan for the shoot, the two men retiring to Ali's guest cabin for the photo.

"It was like a museum — there was a boxing ring and all kinds of memorabilia," Lois remembers. Ali was noticeably struggling with his Parkinson's, often closing his eyes between shots. But then, there was a flash of the old sharpness. "We're taking the photo, standing right next to each other, and he says, 'Hey, George….' And he points to a poster, a blow-up of that cover of St. Sebastian, that was about 15-20 feet away. And he starts pointing [at the arrows]. 'Lyndon Johnson … General Westmoreland … Robert McNamara …' He said the same six names in the same order."

Muhammad Ali, legendary boxing champion and social activist, has died at the age of 74.