Chet Baker and Miles Davis are the two trumpet players most closely associated with the cool jazz movement, though for Davis that is but one of the many subgenres in which he was a major influence.
Both of these artists recorded My Funny Valentine" on numerous occasions with moving and influential results. Baker recorded the tune several times instrumentally, but it is his first vocal version (My Funny Valentine) that proved to be a landmark moment both for him and for the song. Davis, meanwhile, first recorded the song with his classic group of the 1950s (Cookin' With the Miles Davis Quintet), a performance that stands out as one of his most significant ballad performances. His 1964 Carnegie Hall performance (My Funny Valentine) was also noteworthy, helping to signal the new sound of his groundbreaking 1960s unit.
Although Chet Baker's vocal version is one of the best known renditions of this tune, Chet's version with Gerry Mulligan, from 1952 is one of his first recording sessions and is a haunting version of the tune, no doubt helped along by the acoustics of the empty San Francisco Blackhawk nightclub. Baker's approach on this track is strangely reminiscent of Clifford Brown.
Yet another version by Baker/Mulligan, a live date from 1953 (complete with clinking glasses, no less), is two minutes longer than the '52 version and features Baker in a more expansive and looser mode.
You haven't heard 'My Funny Valentine' if you've missed this classic version with Miles on muted trumpet, backed by one of his most famous quintets...- Jon Luthro
Miles Davis My Funny Valentine Original recording 1964
By 1964 Davis was going in an increasingly modern direction and was demanding greater flexibility and interaction from his band. The rhythm section of Herbie Hancock, Ron Carter and Tony Williams was very much up to the task, as evidenced by their epic version of one of Miles' signature tunes.