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Early life
Masekela was born in KwaGuqa Township, Witbank, South Africa to Thomas Selena Masekela, who was a health inspector and sculptor and his wife, Pauline Bowers Masekela, a social worker. As a child, he began singing and playing piano and was largely raised by his grandmother, who ran an illegal bar for miners. At the age of 14, after seeing the film Young Man with a Horn (in which Kirk Douglas plays a character modelled on American jazz cornetist Bix Beiderbecke), Masekela took up playing the trumpet. His first trumpet was bought for him from a local music store by Archbishop Trevor Huddleston, the anti-apartheid chaplain at St. Peter's Secondary School now known as St. Martin's School (Rosettenville).

Apartheid times
n 1961 Masekela went into exile after the political unrest surrounding the 1960 Sharpeville Massacre. Masekela studied at London's Guildhall School, then the Manhattan School of Music. In New York he befriended Harry Belafonte, who helped him to settle in the United States as a student. While in New York, Masekela composed and recorded many new songs; including his 1968 number one hit "Grazing in the Grass", which won him a Grammy for "Best Contemporary Pop Performance - Instrumental" that same year.

Masekela returned to South Africa in the early 1990s and continues to produce music and perform extensive tours around the world. Today, Masekela remains one of South Africa's most celebrated musicians, along with Abdullah Ibrahim and Miriam Makeba. His biggest hit was “Grazing in the Grass,” a peppy instrumental from 1968 with a twirling trumpet hook and a jangly cowbell rhythm. In the 1980s, as the struggle against apartheid hit a fever pitch, he worked often with fellow expatriate musicians, and with others from different African nations. On songs like “Stimela (Coal Train),” “Mace and Grenades” and the anthem “Mandela (Bring Him Back Home),” he played spiraling, plump-toned trumpet lines and sang of fortitude and resisting oppression in a gravelly tenor.

South African trumpeter, fleugelhornist, composer, and singer Hugh Masekela is an acknowledged master of African music. He is also one of his country’s most recognizable freedom fighters in the battle against the racist rule of apartheid. Masekela was born on April 4,1939, in Witbank, a coal mining town near Johannesburg, South Africa. Although his father was a health inspector and acclaimed sculptor, the Masekela home was a modest one, and young Hugh was raised by his grandmother. By age six Masekela was singing the songs of the street and at age nine began attending missionary schools, where he learned to play the piano.

In 2016, at Emperors Palace, Johannesburg, Masekela and Abdullah Ibrahim performed together for the first time in 60 years, reuniting the Jazz Epistles in commemoration of the 40th anniversary of the historic 16 June 1976 youth demonstrations.

Masekela was involved in several social initiatives, and served as a director on the board of the Lunchbox Fund, a non-profit organization that provides a daily meal to students of township schools in Soweto.

From 1964 to 1966 he was married to singer and activist Miriam Makeba. He had subsequent marriages to Chris Calloway (daughter of Cab Calloway), Jabu Mbatha and Elinam Cofie. He was the father of American television host Sal Masekela. Poet, educator, and activist Barbara Masekela is his younger sister.

Career Life After 1994
In 2003, he was featured in the documentary film Amandla!: A Revolution in Four-Part Harmony. In 2004, he released his autobiography, Still Grazing: The Musical Journey of Hugh Masekela, co-authored with journalist D. Michael Cheers, which detailed Masekela's struggles against apartheid in his homeland, as well as his personal struggles with alcoholism from the late 1970s through to the 1990s. In this period, he migrated, in his personal recording career, to mbaqanga, jazz/funk, and the blending of South African sounds, through two albums he recorded with Herb Alpert, and solo recordings, Techno-Bush (recorded in his studio in Botswana), Tomorrow (featuring the anthem "Bring Him Back Home"), Uptownship (a lush-sounding ode to American R&B), Beatin' Aroun de Bush, Sixty, Time, and Revival. His song "Soweto Blues", sung by his former wife, Miriam Makeba, is a blues/jazz piece that mourns the carnage of the Soweto riots in 1976. He also provided interpretations of songs composed by Jorge Ben, Antônio Carlos Jobim, Caiphus Semenya, Jonas Gwangwa, Dorothy Masuka and Fela Kuti.

In 2006 Masekela was described by Michael A. Gomez, professor of history and Middle Eastern and Islamic studies at New York University as "the father of South African jazz."

In 2009, Masekela released the album Phola (meaning "to get well, to heal"), his second recording for 4 Quarters Entertainment/Times Square Records. It includes some songs he wrote in the 1980s but never completed, as well as a reinterpretation of "The Joke of Life (Brinca de Vivre)", which he recorded in the mid-1980s. From October 2007, he was a board member of the Woyome Foundation for Africa.

In 2010, Masekela was featured, with his son Selema Masekela, in a series of videos on ESPN. The series, called Umlando – Through My Father's Eyes, was aired in 10 parts during ESPN's coverage of the FIFA World Cup in South Africa. The series focused on Hugh's and Selema's travels through South Africa. Hugh brought his son to the places he grew up. It was Selema's first trip to his father's homeland.

On 3 December 2013, Masekela guested with the Dave Matthews Band in Johannesburg, South Africa. He joined Rashawn Ross on trumpet for "Proudest Monkey" and "Grazing in the Grass".

In 2016, at Emperors Palace, Johannesburg, Masekela and Abdullah Ibrahim performed together for the first time in 60 years, reuniting the Jazz Epistles in commemoration of the 40th anniversary of the historic 16 June 1976 youth demonstrations.

Masekela's last days
Masekela died in Johannesburg on the early morning of 23 January 2018 from prostate cancer, aged 78.