The band was founded in 1999 in Villa Allemana, a small town in central Chile , by members of the band „Lafloripondio“ , as they returned home from a tour through Germany , Holland , and Austria . Upon his return , Macha , alias Aldo Asenjo , began meeting often with his friend Antonio Orellana , just to play guitar and try out ideas . Gradually , in these sessions , tunes began to take shape 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 Jaunito 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 ability to interpret traditional chilean songs in a new and powerful way. These songs opened new horizons for the band and the mixture of acoustic guitar , vocals , and strong emotion led quickly to a growing circle of fans .
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 filtered and renewed with inspired texts, emotion, and energy .
Chico Trujillo perfomed 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 counrty . They also organized free open air 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 . This happened in part due to a collaboraion with the chilean visual artist Rafael Insunza who was invited to show his works at an exhibition at the „Kunsthaus Tacheles“ in Berlin , an important cultural center symbolic of the reunification of Germany . this idea came forth much earlier in Santiago during evening conversations between Macha and Rafael and in may 2002 Chico Trujillo made their first concerts for a german audience . 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 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 yearsend to play at the closing cerimonies of the „Carnival of the Cultures“ in Valparaiso, together with "Blue Splendor", a band well known in the harbour town. In Feburary 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 and their most beloved newcomer, „Chico Trujullio“.
At the end of this year in Germany they released the album "Fiesta de Reyes", a live album made up of excerpts from four concerts in July. Visiting one of these concerts was Rodrigo Gonzales, better known as „Rod“, the bass player from the famous german punk band, "Die Ärtze". Together with Macha he mixed the live album. Chico Trujillo ended the year in Chile with concerts at the " Carnival of the Cultures " in Valparaiso and, for the fourth year in a row , new years eve at „La Batuta“, the most famous club for rock acts in Chile .
Their numerous concerts in Berlin awoke the interest of concert promoters and club owners all over germany. This enabled them, through the help of their independant label „Hachazo“, to book concerts from May through October. Particularly noteworthy amongst these were the already well known concerts in „Cafe Zapata“, the 1st of May celebrations at the „Treibsands Festival“ in Lübeck , at the „Karnival der Kulturen“ in Berlin , at the „Latin American Festival“ in Hamburg, the "Zytanien Festival" in Lehrte , as well as three concerts opening for „Die Ärtze“ in Oldenburg , Minden , and Darmstadt, each before approximately 20, 000 people. They also performed at the theater ensemble Panoptikum's spectacle "il Corso" 16 nights in a row . As their final concert for the season in Germany on they performed at "Popkomm" at the „Kultur Brauerei“ in Berlin. As they returned to Chile they performed once again at the „Carnival of the Cultures“ in Valparaiso in "Stadion Playa Ancha". The year ended in the south of Chile, in Concepcion, at the newyears eve party "Sur Activo".
To begin the academic year 2006 , which in Chile begins in March , they played at different universities. They also worked on additional material for the new CD. In May they returned to Germany to play in Berlin . Memorable concerts included three shows at the 2006 FIFA World Cup of soccer , at the "Fan Fest" before the Brandenburger gate , as well as countless concerts at „Cafe Zapata“.