Few careers in contemporary music had the arc and the diversity that South Africa-born trumpeter/singer/composer Hugh Masekela did, before he succumbed to prostate cancer on Tuesday at the age of 79. His life was filled with deep musical investigations and global cultural celebrations — both of which he pursued throughout an endlessly successful and inventive 50-plus-year career.

A now-Internet-famous photo of 16 year-old Masekela, exhilarated at receiving a trumpet (supposedly sent to him by Louis Armstrong), betrays the youngster’s excitement about jazz, which was his first love and enduring bedrock. An escape from Apartheid South Africa to New York for music schooling provided a broader education, and a relationship with singer Miriam Makeba opened the door to professional pop gigs, which he also took full advantage of. The spirit of the times continued to move his sound forward. Afro jazz, Summer of Love, Black Power, Pan-Africanism, the rise of disco and club culture, digital recording — all were internalized and used to his devices. Nothing, though, was as influential to Masekela’s music as the plight of his homeland, which he engaged with as an artist, promoted as an ambassador, protested as an activist and documented as a kind of folk sage.

The 15 tracks below are an overview to this arc, touching upon all of these threads. Hopefully, they’re only a first step towards the exploration of a mighty life that saw and heard many changes – some of which Hugh Masekela instigated, and many of which he played. Fearlessly.

The Jazz Epistles, “Dollar’s Moods” (1960)

Jazz Epistle – Verse 1 is a foundational document of South African jazz’s rich tradition. Because the post-bop played by the Epistles — featuring two future giants, the-20 year-old Masekela on trumpet and Dollar Brand (soon to be Abdullah Ibrahim) on piano, as well as alto Kippie Moeketsi, trombonist Jonas Gwangwa, bassist Johnny Gertze, and drummer Makaya Ntshako — locked into its swing like the finest Americans of the time. (The group was modeled on Art Blakey’s Jazz Messengers.) Side one, song one was Hugh’s lone writing contribution. The band did not last.

Miriam Makeba, “Thanayi” (1962)
Hugh Masekela, “Thanayi” (1999)

Years before she recorded it on her second American studio album, The Many Voices of…, Makeba was performing this South African wedding song about the beauty of a girl named Thanayi, with her group the Skylarks. For this spooky, echo-heavy version recorded in the folk-rock style of the era, Masekela added a few spare lines and played a solo counterpoint to his soon-to-be-wife’s vocal and the acoustic guitar. But when revisiting the song on the occasion of his 60^th birthday, it had a party-style gallop and a great vocal courtesy of the incomparable Thandiswa Mazwai.

“Canteloupe Island” (1965)

Upon graduating from the Manhattan School of Music, Masekela set about establishing his jazz bona fides in the States. Despite its horrid title, The Americanization of Ooga Booga, a live quartet gig at a not-so-full-sounding Village Gate that was recorded/produced by Tom Wilson (of Bob Dylan and Velvet Underground fame), kicked off a partnership with pianist Larry Willis and showcased a pan-global take on soul jazz, including this Herbie Hancock classic, which Hugh tears apart.

The Byrds, “So You Want to be a Rock’n’Roll Star” (1967)

Classic rock mythology claims that Byrds bassist Chris Hillman composed parts of this ironic paean to the contemporary musical godhead at a Masekela session, then invited Hugh to craft a trumpet line for it, marking the first time brass had appeared on the Byrds’ recordings. The result is one of the all-time great rock singles, with tongue planted firmly in cheek, a mindfully mischievous sneer and Hugh’s horn flying above it all. In June of that year, the band brought him on-stage to close their set at the Monterey Pop Festival, setting the stage for…

“Grazing In the Grass” (1968)

A slightly funky, cocktail jazz instrumental going No. 1 on the pop charts only seems unlikely if you don’t consider that besides being the Age of Aquarius, 1968 was also the age of Tijuana Brass. (In fact, Herb Alpert’s troop had directly preceded Masekela at the top of the chart with a version Bacharach & David‘s “This Guy’s In Love With You.”) A breezy trumpet-alto duet melody, mirrored by a giddy piano, and driven by drummer Chuck Carter’s “even more” cowbell, it remains a unique smash — especially in the context of its performer’s career.

Hugh Masekela & The Union Of South Africa, “Shebeen” (1971)

The spirit of the times called for more than mere grazing, and following his chart success, Masekela’s music embraced an explicit pursuit of his South African roots and pan-African ideas. “Shebeen” is a wistful slice of guitar-and-brass township soul, written by Epistles trombonist Jonas Gwangwa, who joined Masekela and alto saxophonist Caiphus Semenya in the short-lived Union. Their self-titled album kicked off a distribution deal that Hugh’s Chisa Records had signed with one of the most popular black-owned businesses on the planet, Motown.

“Stimela (Coaltrain)” (1974)

The story of exploited migrants toiling in Johannesburg’s gold mines, the closing track off Masekela’s classic album, I Am Not Afraid, has not only become one of the artist’s most-beloved political standards, but a union anthem as well. It is a roiling epic of a song, guided by the (originally uncredited) piano of The Crusaders‘ Joe Sample and a choir of voices, a few of which belong to members of Hedzoleh Soundz, the percussion-heavy Ghanaian group who served as Masekela’s band in ’73-’74, introduced to him by Fela Kuti.

Ojah feat. Hugh Masekela, “Afro Beat Blues” (1975)

Another Masekela track under the spell of Fela Kuti, but one that did not see the light of day until a 2006 compilation that opened the Chisa records vault. This funky blues takes as its model the Afrobeat music Fela was then bringing to life in Lagos, and its conceit of a traveling unified sound (the lyrics name-check numerous western and southern African countries) from the Nigerian bandleader’s notions on Pan-Africanism. The swirling guitars and Masekela-led brass drive a steady groove.

Miriam Makeba, “Soweto Blues” (1977/1989)

One of Masekela’s best-known and most charged anti-Apartheid anthems was written as a response to, and as direct documentation of, the 1976 Soweto Uprising, which was set off by the government instilling Afrikaans as the official school language of the black townships. Originally recorded for Masekela’s 1977 album, You Told Your Mama Not to Worry (which the streaming music algorithm seems to have lost), it was an instant concert staple for Makeba (which she re-recorded for 1989’s Welela).

“Don’t Go Lose It Baby” (1984)

A revitalization and a sonic update, this synth-heavy track became an international club smash when it was adopted by progressive DJs — most notably, Larry Levan at the Paradise Garage, New York’s trend-establishing, post-disco church of the late ’70s and early ’80s. If Masekela’s rapping on the track was a misstep (it was), its ingredients — Hugh’s trumpet playing against the Fairlight and a bass-synth, creating a kind of proto-house or electro makossa — were not dissimilar to what contemporaries like Miles Davis and Manu Dibango were doing. It certainly re-established Masekela’s club bond, which continued until the end. (Note: the Hot African mix remains pure fire.)

“Bring Him Back Home (Nelson Mandela)” (1987)

As the anti-Apartheid movement swelled in the late ’80s, partially focusing on the release of Nelson Mandela, who’d been jailed since 1962, Masekela wrote an anthem to demand Madiba’s release, then set about playing it throughout Paul Simon‘s massive Graceland world tour. With its organ and vocal choir out front, and Masekela stringing together ebullient horn lines, this was South African gospel music of the best order, almost willing (imminent) freedom into being. Three years later, it was so; and the song’s melody became one of Mandela’s calling cards.

“Lady” (live version 1993)

The synth-heavy, 1985 studio version of Masekela’s only recorded Fela Kuti cover was too lightweight to be a great creative homage; at the time, it served as a reminder that a hugely important international musician (and Hugh’s long-time anti-colonialist co-conspirator) was then languishing in a Nigerian jail. Yet from there onwards, “Lady” rarely left Masekela’s concert set-lists, becoming a centerpiece of his live sets. The version on Hope, a well-received career-spanning live album (recorded at Washington, D.C.’s Blues Alley), is pretty hot.

“The Boy’s Doin’ It (Carl Craig remix)” (2005)

Masekela’s engagement with synthesizers in the ’80s plugged directly into South Africa’s healthy dance music scene, which, with the rise of kwaito in the early ’90s, became fully integrated into the sound the townships and sowed the seeds for Mzansi’s immense and diverse contemporary house scene. Carl Craig, one of Detroit techno’s pre-eminent producers (and one deeply familiar with both jazz and South African music history) decided to pay Masekela forward, with a remix of Hugh’s 1975 Afro-Disco classic, which got love in many clubs and still smokes.

Black Coffee feat. Hugh Masekela, “We Are One” (2011)

Long ready to play the wise elder passing the torch, Masekela lent his voice and trumpet to one of South Africa’s biggest house music artists for a typically humanist statement. His horn dances across Black Coffee’s exceptionally minimal beat and open-chord keyboards, more languidly than it may have in previous years, but with numerous curt, melodic blasts to serve as a reminder. The mere pairing here speaks volumes across generations, genres and genealogies, just as Masekela had for almost his entire life.

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Updated at 3 p.m. ET

Hugh Masekela, the legendary South African jazz musician who scored an unlikely No. 1 hit on the Billboard chart with his song “Grazing in the Grass” and who collaborated with artists ranging from Harry Belafonte to Paul Simon, has died at 78 after a protracted battle with prostate cancer, his family announced Tuesday.

“[Our] hearts beat with profound loss,” the Masekela family said in a statement. “Hugh’s global and activist contribution to and participation in the areas of music, theatre, and the arts in general is contained in the minds and memory of millions across 6 continents.”

Over his career, Masekela collaborated with an astonishing array of musicians, including Harry Belafonte, Herb Alpert, Bob Marley, Fela Kuti, Paul Simon — and his ex-wife, Miriam Makeba. For almost 30 years, “Bra Hugh,” as he was fondly known, was exiled from his native country. And almost despite himself — as he struggled for decades with copious drug and alcohol abuse — Masekela became a leading international voice against apartheid.

The trumpeter, composer, flugelhorn player, bandleader, singer and political activist was born in the mining town of Witbank, South Africa, on April 4, 1939. Growing up, he lived largely with his grandmother, who ran a shebeen — an illicit bar for black and colored South Africans — in her house. (Until 1961, it was illegal for nonwhites in South Africa to consume alcohol.)

Masekela heard township bands and the music of the migrant laborers who would gather to dance and sing in the shebeen on weekends. One of his uncles shared 78s of jazz musicians like Louis Armstrong, Duke Ellington and Glenn Miller. Those two forces, the music and the booze, did much to shape Masekela’s life. He began drinking at age 13.

He was given his first trumpet at age 14 by an anti-apartheid crusader, the Rev. Trevor Huddleston, who was also the superintendent of a boarding school that Masekela attended.

“I was always in trouble with the authorities in school,” Masekela told NPR in 2004.

He had been inspired by the Kirk Douglas film Young Man with a Horn. Huddleston, hoping to steer him away from delinquency, asked what it was that would make Masekela happy. “I said, ‘Father, if you can get me a trumpet I won’t bother anybody anymore.’ “

Masekela soon became part of the Huddleston Jazz Band. And the priest managed to get one of the world’s most famous musicians to send young Hugh a new instrument, as Masekela told NPR in 2004.

“Three years later,” Masekela recalled, “[Huddleston] was deported and came through the United States on his way to England and met Louis Armstrong and told him about the band. And Louis Armstrong sent us a trumpet.”

By the mid-1950s, he had joined Alfred Herbert’s African Jazz Revue in Johannesburg; within just a few years, Masekela was good enough to co-found a landmark South African band, The Jazz Epistles, which also featured another landmark South African artist, the pianist and composer Abdullah Ibrahim. They recorded the first modern jazz record in South Africa featuring an all-black band.

Within months of The Jazz Epistles’ creation, South African police opened fire on thousands of protesters and 69 people were killed in the infamous Sharpeville Massacre of 1960. The apartheid government declared a state of emergency, and The Jazz Epistles couldn’t play together. Meanwhile, Masekela had learned that he was being targeted for his anti-apartheid activities, and he had made friends with a talented singer named Miriam Makeba, who had already fled the country for New York.

Masekela, now 21 years old, was scrambling to secure a passport and papers to study music abroad. And his friendship with Makeba proved crucial, as he told NPR’s Tell Me More in 2013. She and the singer and activist Harry Belafonte became his patrons and mentors.

Masekela had originally planned to head to England to study at the Guildhall School of Music & Drama. But once he was there, Makeba encouraged him to head to New York.

“We’d always dreamt of coming to the States, but she came a year earlier and blew the States away,” he told NPR.

“So she said, ‘Hey, you got to come, forget about London, this is the place to be.’ And she was on a first-name basis with everybody. Then she and Harry Belafonte gave me a scholarship to Manhattan School of Music. I also had to work part time in Harry Belafonte’s music publishing, because they ain’t going to give you no money,” Masekela said.

In short time, Masekela and Makeba became romantically involved; he also recorded with her and appeared on her album The Many Voices of Miriam Makeba. They married in 1964, despite the fact that their relationship was already tempestuous. Their marriage — one of four for Masekela — ended after barely two years.

At night, Masekela would go to the city’s great jazz clubs to catch the likes of Miles Davis, John Coltrane, Thelonious Monk, Charles Mingus and Max Roach. He wanted to be a jazz player in the same bebop style as his heroes, and that’s what he sounded like. But several of those giants gave him some solid advice. One of them was Miles Davis, as Masekela told NPR’s Morning Edition in 2004.

“I have a lot of great musical encounters with Miles, and he said, ‘Yeah. Yeah. You’re trying to play like me,’ ” Masekela said. “Miles was a funny guy. He said, ‘Listen, I’m going to tell you something. You’re going to be artistic because there’s thousands of us playing jazz but nobody knows the s*** that you know, you know, and if you can put that s*** in your s***, then we’re going to be listening.’ “

Masekela decided to put Davis’ advice to work. He put that bleep in his bleep, and began to develop his own, distinctive style — a blend of jazz, soul and one of the South African dance styles he had grown up with: mbaqanga.

It took him a while to get the blend just right. His first solo album was 1963’s Trumpet Africaine. In his 2004 autobiography, inevitably called Still Grazing: The Musical Journey of Hugh Masekela, the artist called that project a “disaster” and an “unlistenable mixture of elevator and shopping mall music.”

By the end of the decade, however, Masekela had pulled it all together and was living in Los Angeles. In 1967, the year his song “Up, Up and Away”was released, he performed alongside Janis Joplin, Otis Redding, Ravi Shankar, The Who and his friend Jimi Hendrix at the Monterey Pop Festival.

A year later, his single “Grazing in the Grass” became a No. 1 hit on the Billboard charts. It was an astounding success — and all the more so as a tossed-off track that the trumpeter recorded with his band as album filler in just half an hour.

In 1977, Masekela’s Soweto Blues, about the anti-apartheid Soweto uprising, was recorded by Makeba, and it reached an international audience. After the stupefying success of “Grazing in the Grass,” however, Masekela largely spent decades living in a haze of drugs, alcohol, bad financial decisions and a string of failed marriages and countless other relationships. He occasionally made music, but he was dumped by label after label; by his own reckoning, he hadn’t played sober since he was 16 years old.

In his autobiography, Masekela estimated that he wasted $50 million, all told. It wasn’t until 1997 that he reportedly got clean; he went on to found the Musicians and Artists Assistance Program of South Africa, to help fellow performers struggling with substance abuse.

He spent stints living in Liberia, Guinea, Ghana and Botswana, where he worked and recorded with a diverse array of African musicians, including leading the Ghanian band Hedzoleh Soundz. He also recorded the anti-apartheid anthem Bring Home Nelson Mandela in 1986.

In 1987, he appeared with Paul Simon on his Graceland album tour alongside South African musicians Ladysmith Black Mambazo and again in 2012 on the 25th anniversary of the Grammy Award-winning album’s release.

Masekela finally returned to South Africa in 1990, following Nelson Mandela’s release. In the meantime, some of his friends and family members were on the frontlines of the new South Africa; his sister Barbara, for example, became her country’s ambassador to the U.S. Upon his return, Bra Hugh was hailed as an elder statesman of South African music, and he subsequently recorded a string of international albums.

Masekela performed at the opening ceremony of the FIFA World Cup and tournament in Soweto’s Soccer City in 2010. That year, Masekela was also given the Order of Ikhamanga in gold, his home nation’s highest medal of honor.

He had been scheduled to tour the U.S. this spring with his former bandmate Abdullah Ibrahim. But last October, he announced that the cancer that he had been battling off and on for nearly a decade had returned.

Among those marking his death is South African President Jacob Zuma, who released a statement on Tuesday: “Mr Masekela was one of the pioneers of jazz music in South Africa whose talent was recognized and honored internationally over many years. He kept the torch of freedom alive globally fighting apartheid through his music and mobilizing international support for the struggle for liberation and raising awareness of the evils of apartheid. … It is an immeasurable loss to the music industry and to the country at large. His contribution to the struggle for liberation will never be forgotten.”

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