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The legendary jazz trumpeter Chet Baker was one of the most iconic jazz figures of the second half of the 20th century. Being one of the greatest exponents of the cool style, he captivated a whole generation of artists, not going unnoticed on the film scene. This artist was a source of inspiration for famed photographer Bruce Weber, who accompanied him during his last year on tour for his documentary Let’s Get Lost. Likewise, the life of this legend has also been brought into the realm of fiction with the biopic of Robert Budreau. This work aims to carry out a comparative analysis between the films Let’s Get Lost (Bruce Weber, 1988) and Born to be Blue (Robert Budreau, 2015). Although both works focus on the life of the acclaimed trumpeter, the approach chosen by the directors is quite different. Thus, the object of study focuses on examining their stylistic and thematic differences, also delving into the profile of each of the directors in order to analyze the control they exercise in their respective films to endow them with a great sensitive and narrative power. In the same way, the use of music in both films will be examined to determine the role that music plays in each of the works and which compositions have decided to be included in one and the other.