The accomplishments of Muhammad Ali are renowned: An Olympic gold medalist, heavyweight boxing champion, humanitarian, civil rights activist. But would you believe he also was a Grammy Award nominee in 1964 and 1976?

Trading in his boxing gloves and shorts for black tie and tails, Ali cut a comedy album inside the Manhattan studios of Columbia Records in early August 1963. A live audience hooted and hollered as the fighter unleashed a volley of jabs and right hooks, but the punches really thrown by the 21-year-old Ali during the recording were of the verbal variety.

The pugilist who stepped before the microphone was not yet a heavyweight champ. He wasn’t even Muhammad Ali at that point. Still known as Cassius Clay, he may only have been a contender for the heavyweight title, but he was already a world-champion entertainer.

“Ali’s genius for marketing was off the charts,” says Jonathan Eig, author of the biography Ali: A Life. “He figured out early on that being an entertainer was good for the boxing business. If he could generate more publicity for himself, he would attract more people to his fights and get an earlier shot at the heavyweight championship.”

With quips as quick as his fists, Ali had earned his “Louisville Lip” nickname. He wielded rhyming couplets like weapons to stagger opponents before bouts and to bolster his fight game.

“The rhythm of my poetry gives me an unprecedented rhythm in the ring,” Ali told the media. Before a March 1963 fight against Doug Jones in New York, the loquacious boxer even took to the stage of a dimly lit Greenwich Village coffeehouse for a poetry battle against seven of the city’s top beatnik poets, a fight he won by popular acclaim.

Ali’s entertaining doggerel and growing fame led Columbia Records to sign him to record a spoken-word album entitled—naturally—“I Am the Greatest.” The tracks, rechristened “rounds” for the album, opened with the sound of a ring bell and featured a blend of stand-up comedy, rhyming verses and comedic sketches. The live audience clapped and cackled as if it were open-mic night at a comedy club as Ali spouted braggadocio such as “This kid fights great; he's got speed and endurance/But if you sign to fight him, increase your insurance.”

Ali mercilessly taunted the reigning heavyweight champion Charles “Sonny” Liston throughout the album. His track “Will the Real Sonny Liston Please Fall Down” is a masterclass in trash-talking. “Friends, Romans, countrymen, lend me your ears. I come to bury Liston, not to praise him,” the “Bard of Boxing” told the audience. “He can’t fight,” Ali said of Liston. “I watched him shadow boxing and his shadow won—in the first round.”

The boxer wasn’t afraid to turn his humor upon himself and give a wink to the audience to let them in on the joke. “Mr. Clay, have you ever been in love?” asked an audience member with a planted question. “Not with anyone else,” the fighter quipped.

Although Ali had a quick wit, he wasn’t freestyling on the album. Columbia Records hired veteran comedy writer Gary Belkin to assist Ali as a ghostwriter. The album’s original liner notes listed Belkin as a producer, but he wasn’t credited as a co-writer until a 1999 re-issue of the album.

Belkin later claimed that he wrote most of the album’s content, but Ali told the Miami News he never paid anybody to write a poem for him—although he conceded Columbia Records could have.

“He put in some of the comedy, some skits,” Ali said of Belkin. “But all my poems are mine.” Evidence submitted to a Senate subcommittee probing boxing corruption in March 1964 suggested otherwise. Included in payments made by Ali’s backers is a $600 expense to Belkin for crafting a poem for Ali's appearance on the “Jack Parr Show.”

No matter who wrote the material, Ali’s critics weren’t impressed. “Cassius, if you look under the surface, is merely loud-mouthing to build a big gate against the retirement into which Liston will blast him,” wrote United Press International sportswriter Oscar Fraley.

When Ali fought Liston on February 25, 1964, he was a 7-1 underdog. Even inside Columbia Records doubts surfaced. “Get the money/Before Clay fights Sonny,” an aspiring poet tacked on a company bulletin board. After pummeling Liston in verse, Ali knocked him out in the ring to become the heavyweight champion.

According to Columbia Records, sales of “I Am the Greatest!” after the fight topped those of Barbra Streisand and even the Beatles. The record company rushed the new champion back into the recording studio to croon a cover of the Ben E. King hit “Stand by Me” and a version of “The Gang’s All Here" with assistance from singer and friend Sam Cooke.

“Ali used to hang around the rhythm-and-blues clubs in Louisville and was a great fan of pop music. He even had a record player in his car,” Eig says. “If he had a chance to become a singer, he would have loved it.”

A quickly issued single featuring a reworked title track from “I Am the Greatest!” and “Stand by Me” sold 100,000 copies in its first week. Critical acclaim followed as “I Am the Greatest!” received a Grammy Award nomination for best comedy performance alongside comedians such as Mel Brooks, Carl Reiner and The Smothers Brothers. All lost that year to Allan Sherman’s recording of “Hello Muddah, Hello Faddah.”

A second Grammy nomination followed for Ali in 1976, after he returned to the recording studio to take on a tougher foe than Liston—tartar. In “The Adventures of Ali and His Gang vs. Mr. Tooth Decay,” the boxer known for his mouth promoted good oral hygiene to kids. The album, which also featured the voices of Frank Sinatra and sportscaster Howard Cosell, received a Grammy nod for best children’s recording.

Although Ali never won a Grammy, his musical legacy endures. His swagger and rhymes have been cited as precursors to the exchange of lyrical blows in modern-day rap battles, and the heavyweight champion has been credited as a hip-hop pioneer by artists such as Chuck D.