Three-time world heavyweight boxing champion Muhammad Ali, who died Friday (6/3) in Phoenix at the age of 74, was one of the most charismatic and outspoken sports figures in history. One of the most recognizable people on Earth, Ali was a towering figure whose name came to symbolize hope, audacity and triumph. He was also Grammy-nominated—twice.

Self-confidence, a quick wit and poetry were as much his trademarks as his astonishing speed in the boxing ring. Born Cassius Clay in Louisville, Ky., in 1942, he was an Olympic gold medalist before turning pro and attracting media attention substantially different from fighters of earlier generations.

In February 1964, while training in Miami Beach for his fight with Sonny Liston, The Beatles attended one of his training sessions for a photo op, as did Malcolm X. After Ali won that fight, he brought his friend Sam Cooke into the ring and attempted to get the singer air time.

Cooke, who was murdered in December 1964, helped Clay get into the record business. Columbia Records released Cassius Clay’s spoken word album I am the Greatest six months before he won the heavyweight crown in 1963 and announced he had joined the Nation of Islam and taken on a new name. It peaked at #61 and, oddly, was nominated for a comedy Grammy.

Columbia released "I Am The Greatest" as a single, with the B-side "Will the Real Sonny Liston Please Fall Down." The lone musical track, a cover of the Ben E. King hit “Stand By Me,” had a second life after it was reissued by Rhino in 1991 on the Golden Throats 2: More Celebrity Rock Oddities compilation.

Columbia even promoted the release with a photo of Ali in the studio with the banner "THE CHAMP SINGS!"

His second album, Ali and His Gang vs. Mr. Tooth Decay, included appearances by Frank Sinatra and Howard Cosell. The 1976 album was nominated for a Grammy in the category of Best Recording for Children.

After defeating George Foreman in the Rumble in the Jungle in 1974, British singer Johnny Wakelin recorded “Black Superman (Muhammed Ali),” which came out on the Pye label in 1975. It hit #7 in England, #21 in the U.S. and topped the singles chart in Australia. Wakelin followed it up a year later with “In Zaire,” which only charted in Europe.

Some consider Ali the godfather of hip-hop. Hanif Willis-Abdurraqib breaks down the Champ’s hip-hop legacy in a fascinating essay posted on mtv.com.

On Friday, Chuck D acknowledged Ali’s passing at the Prophets of Rage show at the Hollywood Palladium; Bob Dylan, Sean Diddy Combs, Lionel Richie, Ben Folds, Quincy Jones and Snoop Dogg were among the musicians who paid tribute to the Champ on social media. Another was Paul McCartney.

"Dear Muhammad Ali. I loved that man. He was great from the first day we met him in Miami, and on the numerous occasions when I ran into him over the years. Besides being the greatest boxer, he was a beautiful, gentle man with a great sense of humour who would often pull a pack of cards out of his pocket, no matter how posh the occasion, and do a card trick for you. The world has lost a truly great man. Love Paul" #PaulMcCartney #MuhammadAli #CassiusClay

A photo posted by Paul McCartney (@paulmccartney) on Jun 4, 2016 at 5:11am PDT