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Muhammad Ali on Ebony’s ‘Black Cool’ cover in 2008

Ali was one of 25 men who epitomized modern cool. The list could have been his alone.

Muhammad Ali, who died on Friday in Arizona at the age of 74, was the greatest of too many things to count, and the best of everything that makes black America supreme.

His posthumous list of “mosts” is enormous. Most famous and charismatic person of the 20th century. Greatest heavyweight boxer of all time. Most polarizing and controversial athlete in modern history. Most unlikely activist (civil rights, religious freedom, human rights, universal love advocate, on and on) whose fortitude under political, professional and personal pressure completely transcends and transforms celebrity.

Back in 2007, when the editorial team at Ebony magazine began work on a special concept package about the “25 coolest brothers of all time,” political candidate Barack Obama was nearing the end of his historic presidential campaign and was creating in real time his own “most” list, said Harriette Cole, Ebony’s former creative director.

“We were really trying to do a list that put our finger on the pulse of what was going on,” Cole said. “It was a time of tremendous possibility for African-American men, and Obama summed up a lot of that swagger.”

Dudley Brooks, Ebony’s photo editor at the time, said Obama and Ali were the two men on the cool list “that no one on staff argued against. Cool is about purpose and focus, and they had it. Ali’s purpose was to turn the basket over and look at what’s in there. He was playing a whole different game.

“The question quickly became, ‘How do you define cool?’ ” Brooks added. “It couldn’t just be about the clothes. It had to be the complete package so that we could narrow it down. The criteria for cool became for guys ‘who would you want to be?’ and for women ‘who would you wanna be with?’ ”

Ali personified black cool in sports and in civil rights, said Bryan Monroe, former vice president of editorial for Ebony and Jet magazines. “As much as it means to be a black man, he stood for something that was definitely bigger than just being an athlete. The staff looked at other prominent athletes like Jim Brown, Michael Jordan and Reggie Jackson, but none of them were even in the ZIP code of Ali.”



After winnowing down their initial list of more than 200 politicians, civil rights leaders, athletes, entertainers, academics and others, Ebony magazine’s editorial team narrowed the group to 25 and decided on an eight-cover run of the “Black Cool” issue. Besides Obama and Ali, the other covers featured singer Marvin Gaye, musician Prince, actors Billy Dee Williams, Denzel Washington, Samuel L. Jackson and rap mogul Jay Z.

Choosing the perfect cover image of Ali meant narrowing down the thousands of photos showing The Champ in his heyday as a boxer, though there were also plenty of iconic images of him out of the ring.


UNITED STATES - MARCH 02: Cassius Marcellus Clay (Muhammad Ali) with Black Muslim leader Malcolm X at 125th St. and Seventh Ave.

UNITED STATES – MARCH 02: Cassius Marcellus Clay (Muhammad Ali) with Black Muslim leader Malcolm X at 125th Street and Seventh Avenue.

John Peodincuk/NY Daily News Archive via Getty Images

The now-famous series of photos from 1964 showed Cassius Clay in Harlem with Malcolm X, and highlighted the outspoken Kentucky native’s classic sense of style.

“The photos from the Nation of Islam years were incredibly striking,” Brooks said. “Ali was extremely neat and precisely groomed. It may have been a Nation of Islam uniform, but it wasn’t an overstated style.

“He did the styles of the times, but he did them really well,” added Brooks. “But that also weaves into the larger thing: The overall style impact is about standing up. If you say this is your mission, do it.”

Ali “was always dressed as a gentleman,” Cole said. “There were lots of men of his time who dressed like ‘Superfly,’ but he didn’t dress like that, which may be one reason pictures of him still don’t look dated. He was a man with a lot of revolutionary thoughts and he dressed like a businessman.”


American heavyweight boxing champion Muhammad Ali wearing a smart suit and a thoughtful expression, 4th January 1972.

American heavyweight boxing champion Muhammad Ali wearing a smart suit and a thoughtful expression, Jan. 4, 1972.

Michael Fresco/Evening Standard/Hulton Archive/Getty Images

Among contemporary athletes, there are those who try their hand at the style game, whether it’s Cleveland Cavalier LeBron James or retired basketball player Shaquille O’Neal or former world champion boxer Manny Pacquiao, but none of them can touch Ali, said Monroe.

“Ali was the original braggart, the poet and philosopher, the comedian and the statesman,” he added. “All these current athletes will have to do a lot more work and become more multifaceted if they want to have his impact. Because it’s more than just putting a ball in a hoop.

“[Michael] Jordan had the talent and braggadocio thing, but off the court, he’s a one-note song,” Monroe said. “It’s all about Jordan. The real Ali was the force standing for himself and for black America and being unapologetic and strong.”


Jill Hudson is the senior style writer for the Undefeated. She is an evolved nerd, a caffeinated shoe fanatic, and a maker of long lists and perfect martinis.