The band was founded in 1999 in Villa Alemana, a small town in central Chile, by members of the band "Lafloripondio", as they returned home from a tour through Germany, The Netherlands, and Austria. Upon his return, Aldo Asenjo aka Macha, began meeting often with his friend Antonio Orellana, just to play guitar and try out ideas. Gradually, in these sessions, they began to compose songs such as, "Cabildo", "Me convertiste en santo" and "Dejame decirte algo" and later, at the beginning of 2000, "Tongoy" and "Maria, ria" .

Later, Tuto Vargas and Juanito Gronemeyer, the bass player and percussionist from "Lafloripondio" respectively, also joined the sessions. This formation developed the foundation for further compositions. Eventually they invited Chapa, on the percussion, and Tio Rodi, on drums . This was the formation and it remained unchanged until 2001 when they added a horn section, and Michael Magliocchetti on guitar. They recorded their first album "Chico Trujillo y la Señora Imaginacion", released in Germany as "Arriba las Nalgas". With this album the band showed its interpretation of traditional Chilean songs and rhythms blending acoustic guitars, vocals, with the rest of the instruments.

In live concerts, the mixture of traditional cumbias like "El Tren", and "Pedacito de mi vida", was expanded. The band performed primarily cumbias, boleros and ska with renewed texts.

Chico Trujillo performed concerts in the Chilean festival Huachaca, for the "Comite de Liberacion de los Presos Politicos Mapuches", as well as live television performances as part of the "Festival del Huaso de Olmue", the most important folk music festival in the country. They also organized free open concerts and self promoted shows in clubs and bars all over Chile, including the legendary concerts at "La Batuta" in Santiago. In 2002 they made their first tour in Germany in collaboration with the Chilean visual artist Rafael Insunza who was invited to exhibit his pieces at the "Kunsthaus Tacheles" in Berlin. They performed in "Tacheles" in "Cafe Zapata", in the presentation "No al Plan Colombia" at "Humboldt University", in "Kunsthaus Köpi" at the "Festival Liberacion de los Presos Politicos de Chile" as well as in numerous "fiestas latinas".

It was at this time that the band gave their first performances in Spain, la Coruna, Ferrol and Oliera. As they returned to Chile they were invited at the end of the year to play at the closing ceremonies of the "Culture Carnival" in Valparaiso, with "Blue Splendor", a band well known in the harbor area. In February 2003 they played once again at the "Festival del Huaso de Olmue", a program followed by more than 4 million television viewers in Chile alone. There they performed with "Tommy Rey" and "Gioloto y su Combo" at "Cumbre de los Sonoras", a meeting of Chile's best known bands.

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