In the group's beginnings they lacked extensive material resources to create music, but this didn't prevent them from releasing their creativity, feelings and social commitment with the community. In 1999 they came out with their first release, Legua York. Despite using other bands' musical tracks and having to resort to the poor sound quality of cassette recordings, with this production they made a name for themselves in Santiago's rejuvenated hip hop scene. In 2000 Legua York released their second cassette, Remasteriza'o, this time using their own tracks. At the beginning of 2001 they undertook a new record project that would come to be known as Este con Mayo (a popular "Chilenism" that roughly translates to "this one with mayonnaise"). With the collaboration of Tea, a French hip hop musician of the Paradais Apokalistik grou, Legua York's third cassette laid out the groundwork for their forthcoming work: generating and maintaining a collective social consciousness through diversion, education and struggle. At the beginning of 2003, Legua York signed a contract with the Chilean label Alerce/La Otra Música.
Soon after, "Antología Underground 1997-2003 was released, collecting the most significant tracks of the group's six-year trajectory and adding two new axes to their musical proposal: interchange (other musical artists are invited to collaborate on tracks) and internationalism (their lyrics are in Spanish, Mapudungún [a language spoken by indigenous groups in Chile and Argentina], French and Portuguese). In 2004, Legua York formed the Colectivo Agosto Negro ("Black August Collective"), inspired by the African-American movement Black August. The Colectivo Agosto Negro integrated groups from across Chile and organized concerts and informal courses on hip hop culture. In mid-2004, the collective produced the CD Hip-hop sin fronteras ("Hip-Hop Without Borders"). Released by Alerce, the compilation featured 19 groups from Chile and around the world.
In August of the same year, Legua York organized the free Black August Festival, the first of its type in South America. The festival brought together 50 bands from around the country and was attended by 3,000 people, becoming a milestone in Chilean hip hop. After almost a year of work in Alerce's recording studios, Legua York released a new CD at the end of 2004 titled Huelga de hambre ("Hunger Strike"). Among the invited artists featured on its tracks were Claudio Narea (ex-guitarist of Los Prisioneros), Amaro Labra (Sol y Lluvia vocalist), Ana Tijoux (MC of Makiza) and Francisco Villa. The quality of the album was recognized by the specialized press and firmly established Legua York as one of the most important influences Chilean hip hop at the turn of the 21st century.
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