The Legendary Riverside Albums / Chet Baker Sings – It Could Happen to You / In New York / Chet / Chet Baker Plays the Best of Lerner and Loewe / Outtakes and Alternates

Chet Baker had two careers. Through the mid-1950s, he was one of the biggest stars in jazz, a strikingly beautiful man who played trumpet and also sang in a strange and androgynous voice that seemed too fragile for this world. He won both critics’ and readers’ polls in DownBeat magazine, and his recordings, particularly his early work with baritone sax player Gerry Mulligan, were essential documents of West Coast jazz. But in the years following Baker’s descent into heroin addiction, he became a cult artist, a figure whose musical output was often eclipsed by the tragic narrative of his life. His gaunt and caved-in face told the story of a promising young talent gone to seed.

In the late ’50s, after his first run of legal problems connected to his accelerating drug use, Baker spent a year cutting albums for the Riverside label. It was a transitional period, a moment when Baker hovered between one career and the next. He still sounds young—he would turn 30 just after recording these LPs—and he’s surrounded by top-shelf supporting musicians, the kinds of bands that would be difficult for Baker to assemble once he became an industry pariah.

Baker began his year on Riverside with It Could Happen to You, a vocal album aimed at a pop-leaning audience. His singing—unsteady in pitch, frail and delicate, with a disorienting mix of sexiness and naiveté—has always been an acquired taste, but there’s a context for it now that didn’t exist then. Its damaged innocence and dreamy loveliness carry a hint of irony that, 60 years on, brings to mind sounds we might hear in the unlit corners in David Lynch’s universe. You can hear that quality all over It Could Happen to You—take “My Heart Stood Still,” where Baker sings at the higher end of his natural range for an effect both chill-inducing and slightly creepy. Outtakes and Alternates is heavy on vocal numbers from the It Can Happen to You sessions. Some songs are even more haunting (“While My Lady Sleeps” is downright gothic, with Baker close to the microphone and singing way behind the beat), while others were shelved for a reason (he sounds especially high on this alternate take of “Everything Happens to Me” and struggles to articulate some words). If you can tune into Baker’s unsteady frequency, the voice showcased here is like nothing in jazz.

Baker was obsessed with Miles Davis’ cerebral Birth of the Cool and one can trace a significant portion of his trumpet style to those sessions. Like Davis, Baker mostly avoided the extremes of his horn’s range and focused on its middle, the frequency band where his melody lines could evoke a human voice. He had a natural ear for phrasing, and would alter the melodies of familiar tunes to wring a maximum amount of feeling from a minimum number of notes. Chet Baker in New York pairs Baker with two veterans of Davis’ rhythm section, bassist Paul Chambers and drummer Philly Joe Jones, along with Al Haig (who played with Charlie Parker) and saxophonist Johnny Griffin. Continuing the homage, the group even tackles Davis’ tune “Solar.” Baker was strung out and in rough shape around the time In New York was cut, and the idea, according to Riverside label owner Orrin Keepnews (who also produced the session), was to “cover him over cosmetically with the best supporting cast, try to bury him.” To an extent, the approach worked. “Polka Dots and Moonbeams” is lush and romantic—a little vacant, maybe, but easy to get lost in—while “Hotel 49” is a satisfying 10-minute blues on which Griffin shines.

Much better is Chet, a set of pure floating atmosphere cut directly after In New York. Most of the tunes were recorded with pianist Bill Evans, who was at a peak moment of his career, and his style fit perfectly with Baker’s. “It Never Entered My Mind” is a poignant showcase for Baker’s horn, his judicious use of vibrato elevating the sadness as the rest of the ensemble falls in the mix to allow his phrases to linger. On some tunes Baker plays eloquently with other soloists: A duet with baritone saxophonist Pepper Adams on “’Tis Autumn” allows their horns to entwine as if in an embrace. On “Alone Together,” Evans improvises a haunting opening refrain that sounds like a trial run for “Blue in Green,” the piece he would record with Davis on Kind of Blue a few months later. Mature and beautiful, with a great selection of songs rendered in slow motion, Chet is one of Baker’s best albums.

Plays the Best of Lerner & Loewe, another instrumental LP cut later in 1959, finds Baker paying homage to the composers of My Fair Lady. It’s the weakest of these records, though it has its charms. Ballad-heavy and recorded with heavier reverb, there’s something almost crass about it, a sickly glamour that sounds good in the right mood. Baker completed it after serving several months at Rikers Island, and the rest of the 1960s were disastrous for him: an endless series of busts and jail time, mostly in Europe, that led to his expulsion from several countries. In 1966, he was injured in an assault likely related to a drug deal; he lost some teeth, impairing his ability to play, and his music career ground to a halt. Eventually he returned, first to make novelty records that ought to count as some of the worst music ever made—try “Sugar, Sugar,” from Blood, Chet and Tears—and then for the decades-long cult period, in which he recorded and gigged constantly and once in a while made something great. The Riverside period, flawed but occasionally brilliant, is the last, missed exit before he got on that road.

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