Trumpet, Flugelhorn, Vocals | 1929-1988

Chesney Henry Baker Jr., nicknamed "Prince of Cool", was jazz's most romantically tragic figure, combining lyrical trumpet mastery with achingly vulnerable vocals. Rising to fame at 23 with Gerry Mulligan's pianoless quartet in 1952, his rendition of "My Funny Valentine" became his signature. Baker won 1953 and 1954 polls beating Miles Davis and Clifford Brown, whilst his vocal debut Chet Baker Sings (1954) showcased a light, vibratoless tenor that launched him to teen idol status. His matinee idol looks epitomised West Coast cool jazz, though heroin addiction led to arrests and inconsistency throughout the 1960s.

The 1959 album Chet, featuring Bill Evans, Paul Chambers, and Philly Joe Jones, captured his lyrical peak. After European deportations and jail time, Baker mounted a remarkable 1970s comeback, with critics praising his late-period playing as matching his 1950s work despite addiction's toll on his voice. His final decade proved prolific, the years 1977-1988 showing more forceful attack and intimate tone. He died falling from an Amsterdam hotel window in 1988 aged 58. His legacy grew posthumously through Bruce Weber's documentary Let's Get Lost and unfinished memoir As Though I Had Wings, cementing his status as cool jazz's most influential and tragic voice.