Five Chet Baker albums you should actually own, in the order you should own them. Not My Funny Valentine. Not yet. Probably not ever as a starting point.
What is the best Chet Baker album to start with?
Chet Baker Sings (Pacific Jazz, 1956). Not because it is the most interesting album he made — it isn't — but because it is the most approachable, and approachable matters when you are handing someone a record and asking them to trust you. The voice is the entry point. The trumpet comes after. Most people who become serious Baker listeners started with the voice and arrived at the trumpet six months later, a little stunned to realize they'd been missing half the catalogue.
The album was recorded when Baker was twenty-six, already famous on the West Coast after the Gerry Mulligan Quartet recordings, and already in the early stages of the self-destruction that would define the rest of his life. None of that is audible on Chet Baker Sings. What is audible is a young man singing as if the only person in the room is you.
Why should I not start with My Funny Valentine?
Because My Funny Valentine (Pacific Jazz, 1954) is a live recording, and live Baker is not where you start. The sound is thin — this was a Los Angeles club in 1954, not a studio with Richard Bock producing — and the album is twenty-six minutes long, which is not enough time to fall in love with anything. It became the symbolic Chet Baker title because the song became the symbolic Chet Baker song, and because a record with that title on the cover is a satisfying thing to own as an object. It is not a satisfying thing to listen to if you have never heard him before.
The people who recommend My Funny Valentine as the starting point are the same people who recommend Kind of Blue as the only Miles Davis album a person needs. They are not wrong about the quality. They are wrong about the pedagogy. Start with the thing that pulls you in, not the thing that confirms what you already thought you knew.
I have watched people buy My Funny Valentine at a record fair, play it twice, and conclude that Chet Baker was overrated. He is not overrated. They picked the wrong door.
The five albums you should actually own
1. Chet Baker Sings (Pacific Jazz, 1956) — start here
The opening track is "That Old Feeling." Baker's voice enters, and there is an immediate question: is this a man or a recording of a ghost? The voice is light, high for a man, and positioned as though he is not so much projecting as simply present. It has no armor. That lack of armor is the whole thing.
The Penguin Guide to Jazz (Cook and Morton) rates Chet Baker Sings as a core collection item — the designation they give records you should own, not merely hear. The critical consensus and the popular consensus align here, which is rare enough to be significant. This is the album where Baker is most available to a new listener.
The tracks to pay attention to first: "The Thrill Is Gone," "But Not for Me," "Time After Time." By the third one, you will either be completely under or politely interested. Both are legitimate responses. The former means you will spend the next several years tracking down Pacific Jazz pressings.
2. It Could Happen to You (Riverside, 1958) — the trumpet
By 1958, Baker had moved to Riverside Records and was recording primarily as a trumpeter. It Could Happen to You is the album where the two sides of his artistry — voice and instrument — feel equally weighted. He sings on roughly half the tracks; on the others, the trumpet carries the melody with the same absence of force, the same interior quality.
This is the record where people who started as Baker Sings fans discover that the trumpet is not a concession and not a detour. The trumpet is the real thing. The voice was just the door.
Producer Orrin Keepnews, who recorded Baker for Riverside during this period, was also the producer behind the canonical Thelonious Monk records of the same era. The production is clean, intimate, and never tries to make Baker sound larger than he is. That is the correct instinct. The entire appeal depends on the smallness.
3. Chet (Riverside, 1959) — strings done right
Chet (Riverside, 1959) is the strings album, which ought to be a warning but isn't. Most jazz-with-strings projects use the strings as decoration, a layer of warmth-for-warmth's-sake that softens whatever made the artist interesting in the first place. Arranger Johnny Mandel did something different. The strings on Chet are sparse, precisely placed, and never compete with the trumpet. They provide a frame. Baker provides everything inside it.
This is the album I put on when someone comes to the house who is skeptical of jazz. Not hostile — skeptical. The person who likes music but has never found a reason to sit still for a trumpet solo. Chet gives them that reason. The strings make it permissible to be moved before you've developed the vocabulary to explain why.
On vinyl, this record is extraordinary. The Riverside reissues are serviceable; the Analogue Productions 45 RPM reissue, if you encounter it, is a different experience entirely — the kind where you sit down with your Sancerre and do not move for forty minutes.
4. Embraceable You (Pacific Jazz, 1957) — the overlooked one
This album exists in the gap between the famous early records and the more seriously discussed later ones. It is almost never on the recommendation lists. It should be.
Embraceable You is quieter than Chet Baker Sings and more plainly about the trumpet than It Could Happen to You. Baker is working through a set of standards — the title track, "How High the Moon," "Moonlight in Vermont" — with the same economy he brings to everything, but there is a patience here that the earlier records don't quite have. He was twenty-seven or twenty-eight when these sessions were recorded. The voice of a very young man who was learning, slightly more slowly, to hold something back.
The reason it doesn't appear on recommendation lists is simply that it doesn't have a famous song on it, and recommendation lists are usually organized around songs people already know. Ignore that. Own this record.
5. Chet Baker in Tokyo (Electric Bird / Enja, 1987) — the late period
This one is not comfortable. I want to be clear about that before you decide whether to continue reading this section.
By 1987, Baker was fifty-eight years old, had been through a narcotics conviction, a period in Italian prison, the near-loss of his embouchure after a violent assault in San Francisco in 1966 that shattered his front teeth, and decades of use that had remade his face into something his younger self would not have recognized. The technique he had in 1956 was gone. What remained was an instinct for where the emotional center of a melody lives, and the willingness to go there even when the technical means were failing.
Chet Baker in Tokyo is the best document of that late period. Recorded live at Nemo Studio in Tokyo, it captures a trumpet player who no longer plays with facility and who plays anyway — who finds a phrase, holds onto it, and means every note in a way that the young prodigy in the Pacific Jazz sessions never needed to mean anything, because everything came easily. Easy and inevitable are not the same thing. Chet Baker in Tokyo is the proof.
This is not the fourth album you listen to. It is the tenth, or the twentieth. But once you've earned it, it is the album you come back to. I've played it at the end of dinner parties when the room has gone quiet and nobody wants to leave. Nobody does.
Where do most people go wrong with Baker?
Two places. First, they buy My Funny Valentine because the title is on every recommendation list that exists, play it once, find it too short and too thin-sounding, and conclude he is overrated. He is not. They heard the wrong record.
Second, they listen to the early Baker and then skip straight to Miles Davis, because the cultural narrative says Baker is the minor key and Davis is the major. This is wrong in an interesting way. Baker and Davis were contemporaries, both influenced by the same cool jazz currents coming out of the Claude Thornhill Orchestra and the Miles Davis Nonet recordings of 1949-1950. They were doing different things. Davis was building toward something larger. Baker was going further inside. Both directions are valid. The one that goes further inside requires more patience from the listener, which is probably why it's undersold.
Does the order of listening matter?
More than people admit. Chet Baker Sings first, because the voice establishes the emotional register. Then the trumpet records, because by then you understand what he is reaching for. Chet Baker in Tokyo last, because it only makes sense as a conclusion. Played out of order, it sounds like failure. Played in sequence, it sounds like honesty.
The sequence I've described is not the only way in. But it is the way that has the highest rate of making someone a serious Baker listener rather than a casual one. A serious Baker listener will, over time, track down the Gerry Mulligan Quartet recordings, the Italian period recordings, the Enja label sessions. A casual listener will have Chet Baker Sings and be satisfied with that. Being satisfied with that is perfectly fine. It just means you've stopped at the door.
I've been playing Baker on my Marantz since before your parents had heard of him. If you want to argue about whether the 1959 Chet is better than the 1956 Sings, or whether I'm wrong about the Tokyo record, come find me. Bring something worth drinking.
