The urban sounds of the townships, the influences of the Manhattan Brothers, Dorothy Masuka, the Dark City Sisters, the Mahotella Queens and Mahlathini, Ladysmith Black Mambazo, Miriam Makeba, Spokes Mashiyane, Lemmy Mabaso, Elijah Nkwanyana, Kippie Moeketsi, Mackay Davashe, all these form an intrinsic part of his musical roots, intertwined with vivid portraits of the struggles and the sorrows, the joys and passions of his country.

After Huddleston asked the leader of the Johannesburg "Native" Municipal Brass Band, Uncle Sauda to teach him the rudiments of trumpet playing, Hugh quickly proceeded to master the instrument after having been inspired by the film "Young man with a horn" in which Kirk Douglas portrayed the great American Jazz trumpeter, Bix Beiderbecke.  Soon, some of his music loving schoolmates also became interested in playing instruments, leading to the formation of the Huddleston Jazz Band, South Africa's very first youth orchestra formed at St. Peters Secondary School where the anti-apartheid priest was chaplain.

Huddleston was deported by the racist government of the time for his emancipation militancy and when Hugh kept on badgering him to help him leave the oppressive country for music education opportunities abroad, the priest worked very hard to get him to England.  After playing in other dance bands led by the great Zakes Nkosi, Ntemi Piliso, Elijah Nkwanyana and Kippie Moeketsi among others, he joined the star studded African Jazz Revue in 1956.  Following a Manhattan Brothers tour of the country in 1958, he ended up playing in the orchestra for the "King-Kong" musical written by Todd Matshikiza, with Jonas Gwangwa and some of the afore mentioned musicians.  King-Kong" was South Africa's first record breaking blockbuster theatrical success that toured the country for a sold  out year with Miriam Makeba and the Manhattan Brothers' Nathan Mdledle in the lead.  The musical later went to London's West End for two years.  At the end of 1959, Abdullah Ibrahim, Kippie, Jonas, Makhaya Ntshoko, Johnny Gertze and Hugh formed Jazz Epistle Verse 1, the first African group to record an LP and perform to record-breaking audiences in J.H.B. & Cape Town through late 1959 to early 1960.

After the March 21, 1960 Sharpville Massacre where 69 Africans peacefully protesting the pass laws along with thousands of their fellow comrades were mercilessly mowed down, the ensuing national outrage caused the government to proclaim a state of emergency and the banning of gatherings by more than ten people.

As the brutality of the Apartheid state increased, Hugh finally left the country with the help of Trevor Huddleston and his friends Yehudi Menuhin and Johnny Dankworth who got him admitted into London's Guildhall School of music.  Miriam Makeba who was already enjoying major success in the USA later helped him with Harry Belafonte, Dizzy Gillepsie and John Mehegan, to get admission to the Manhattan school of Music in New York.  Hugh finally met Louis Armstrong who had sent the Huddleston Band a trumpet after Huddleston told the trumpet king about the band he helped start back in South Africa before his deportation.

With immense help from Makeba and Belafonte, Hugh eventually began to record, gaining his first breakthrough with "The Americanization of Ooga-Booga" produced by the late Tom Wilson who had been producer of Bob Dylan and Simon & Garfunkel's debut successes.

Stewart Levine, his business partner in Chissa Records went on to produce hit records for Hugh on Uni Records,  beginning with the "Emancipation of Hugh Masekela" followed by "Alive and Well at the Whiskey" in 1967 and then "Promise of A Future" which contained the gigantic hit song "Grazing in the Grass" in 1968.

By the beginning of the 1970's he had attained international fame, selling out all of America's festivals, auditoriums and top niteries.  Heeding the call of his African roots, he moved to Guinea, then Liberia and Ghana after recording the historical " Home is where music is" with Dudu Pukwana.

After a pilgrimage to Zaire in 1973, Hugh met Fela Kuti in Nigeria who introduced him and Stewart Levine,  to "Hedzoleh Soundz" a grassroots Ghanaian band.  For the next five years they produced a string of ground breaking records, which included international favourites such as "The Marketplace", "Ashiko".  "The Boy'z doin it", "Vasco Da Gama", "African Secret Society" and the evergreen "Stimela".  After a tour and two duet albums with Herp Albert, Hugh and Miriam played a Christmas Day concert in Lesotho in 1980 where 75 000 people came to see them after they had been away for 20 years from the region.  In 1981, Hugh moved to Botswana where he started the Botswana international School of Music with Dr. Khabi Mngoma. His record label Jive Records, helped him to set up a mobile studio in Gaborone where Stewart produced "Techno Bush" from which came the hit single "Don't Go Lose it Baby" in 1984.  He unexpectedly had to leave with his band Kalahari for England, after his childhood friend George Phahle, his wife Lindi Phahle along with 14 people were murdered by South African defence force death squads in the pretext of raiding "communist terrorist camps" manned by South African Anti-Apartheid activists.

While in England, Hugh conceived the Broadway musical "Sarafina" with Mbongeni Ngema and recorded another runaway song "Bring Back Nelson Mandela bring him back home to Soweto" with Kalahari in 1986.  After touring in "Graceland" with Paul Simon, Black Mambazo and Miriam Makeba, Masekela returned home following the unbanning of political parties and the release of Nelson Mandela in 1990.  In 1991, he launched his first tour of South Africa called "Sekunjalo, This is it" with Sankomota and Bayete.  It was a four-month tour, selling out in the country's major cities. His recent albums "Black to the Future", "Sixty", "Greatest Hits" and "Time" have all gone platinum.  2004 saw the publishing of "Still grazing " Hugh's biography which was published by Random House in New York.

He uses his position to give a platform to a fresh generation of South African talent, some of whom will be performing with him on his tours.

Masekela was heavily influenced by African-American music since his infancy, having been raised on the 78 RPM gramophone records of Louis Armstrong, Jelly Roll Morton, Bessie Smith, Ma Rainey, Chick Webb, Ella Fitzgerald, Sy Oliver, Lucky Millinder, Duke Ellington, Count Basie, Erskine Hawkins, Coleman Hawkins, Cab Calloway, Fats Waller, Sarah Vaughan, Billy Eckstine, Louis Jordan, The Ink Spots, The Mills Brothers, Billie Holiday and Charlie Christian.  In his teens, he fell in love with Dizzy Gillepsie, George Shearing, Miles Davis, Clifford Brown, Coltrane, Cannonball, Horace Silver, Art Blakey, Lee Morgan, Kenny Dorham, Oscar Peterson, Bud Shank, Dave Brubeck, Paul Desmond, Stan Getz, Jackie & Roy Kral, June Christy, Shorty Rogers, Gerry Mulligan, Chet Baker, Bud Powell, and Mahalia Jackson.  He went to Manhattan School of Music with Dave Grusin, Herbie Hancock, Chick Correa, David Izenzon, Donald Byrd, Eric Dolphy,  Edie Gomez, Richard Davis, Ron Carter and many other jazz greats.

He played on some of Bob Marley's very first recordings and his music has very strong Brazilian, Nigerian, Ghananian and Congolese influences.

Hugh Masekela has just released a new album called "Revival" produced by Zwai Bala and Godfrey 'Guffy' Pilane, both of whom are considered to be hip hop, kwaito musicians.  However their collaboration with Hugh destroys that myth and shows them to be extremely gifted and well rounded musicians instead.

Hugh Masekela has also just recorded an album of old and popular standard ballads with a trio led by his Manhattan School of music classmate Larry Willis from 43 years ago.  Larry played piano in Hugh's debut american quartet which recorded the classic "The Americanization of  Ooga Booga" album in 1965.  Along with bassist John Heard and drummer Lorea Hart, they completed a 3 day live recording of the love songs.  This had been a dream of theirs for 4 decades.  The album is called "Almost like being in Jazz" and will be released in late 2005, a year during which Hugh Masekela will tour the USA, Europe, Asia and his home country extensively.  Hugh is still grazing after all these years.