Since Chet Baker's death in 1988, the trumpeter and vocalist's legacy has been widely debated within the jazz world. Called the "Prince of Cool," Baker amassed significant career accomplishments that were too often overshadowed by the attention to his drug addiction. His drug problems were significant, but they don't dismiss his charismatic artistry and distinct phrasing.

Thankfully, the upcoming not-quite-biopic Born To Be Blue acts as an entry point for those looking to re-examine Chet Baker. In the film, which sees a limited theatrical release in the U.S. Friday, Baker is given commanding new life by actor Ethan Hawke and director Robert Budreau. Born To Be Blue takes artistic liberties with Baker's life story, but key details are there: his 1954 debut as a bandleader, his prison sentence in 1960s Italy, the mugging that destroyed his teeth and forced him to re-learn his instrument.

What does the film leave out? Chesney Henry "Chet" Baker Jr. was born in Yale, Okla., raised by a father who was a professional guitarist and a mother who was an amateur pianist. After high school, Baker would spend the next few years between Army jazz bands and formal musical education. He caught a significant break in 1952 when he joined bebop pioneer Charlie Parker for a string of West Coast dates, and reached a wider audience when he joined the piano-less quartet of baritone saxophonist Gerry Mulligan.

Baker made his official debut as a bandleader in 1953, after his time with Mulligan's quartet, and introduced himself as a vocalist in 1954. The spark of attraction that persisted throughout his career was twofold: the organic, conversational, fluid phrasing he employed as a trumpeter, and the cool attitude that pervaded both vocal and instrument. Listening to standards Baker recorded in the early '50s, you hear a man defiantly aloof, who almost rolls his eyes at the rosy romances constructed by Cole Porter, Lorenz Hart and other songwriters. But other recordings show the vulnerability concealed behind the mask of cool — the core of an emotional being that could quickly adapt the sound of his horn in whichever musical situation he found himself.

Here are five songs that exemplify the charms and chops of Chet Baker.

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