How does jazz work?

Rather than attempting the impossible task of explaining how everything in jazz works, I’m going to pick a specific tune and talk you through it: “Someday My Prince Will Come” by Miles Davis, off the 1961 album by the same name.

First, here’s the original version of the tune from Snow White.

Once you’ve got the melody in your head, listen to the Miles Davis recording.

The tune begins with an extended intro section. Bassist Paul Chambers plays the same note over and over, a technique known as pedal point. The pedal point creates a feeling of floating suspense. Drummer Jimmy Cobb plays gentle waltz time with his brushes: “one two three, one two three.” (Most jazz tunes are in four-four time, meaning you’d count “one two three four, one two three four.”) Pianist Wynton Kelly plays some improvised figures based on broken-up chords.

At 0:40, Miles Davis enters, playing the melody on muted trumpet. He interprets the tune’s timing loosely, and he adds plenty of his own ornaments. Still, you should have no trouble singing the words along with him. This statement of the melody is called the head. Here’s a chart, if you’re a music reader. The head is thirty-two bars long, meaning it lasts as long as it takes for you to count “one two three” thirty-two times. This is typical; most jazz heads are thirty-two bars long.

At 1:17, Miles begins his solo. Over the same thirty-two bar form of the head, he improvises a new melody. He chooses his notes spontaneously, but not randomly because his solo has to make sense against the song’s chords as they go by. You can keep track of the form by continuing to sing the words. As you do, hear how Miles’ solo interacts with the original melody.

Miles is famous for his dark and moody style, and for his unhurried pacing. He plays fewer notes than his virtuosic sidemen, and he inserts long silences. You can hear him going back and forth between two styles different improvisational styles. Sometimes he plays tunefully, referring back to the song’s original melody. Sometimes he plays abstractly, creating note patterns with their own internal logic, even if they rub tensely against the chords. Miles is a perfect entry point for jazz — his lines are simple enough to follow and memorize, but they’re rich with emotional and intellectual nuance.

Each pass through the thirty-two bar form of the song is called a chorus. Miles plays three choruses — you can sing the words three times over his solo. At 2:26, Miles ends his second chorus with a funky repetitive riff, one note over and over. At 3:05, the end of the third chorus, he reiterates this one-note riff and extends it, allowing it to spill over past the end of the form. This kind of casual disregard for convention is classic Miles.

At 3:11, there’s a more energetic feeling in the drums as Jimmy Cobb switches from the soft-sounding brushes to the louder and more percussive sticks. This is where Hank Mobley begins his tenor saxophone solo. Hank is a world-class saxophonist, but “Someday My Prince Will Come” isn’t one of his strongest recordings. He was new to Miles’ band at the time of the session, and he didn’t yet have his feet under him. Also, his lyrical style sounds a little schmaltzy compared to Miles’ acidic tone. If you want to hear Hank at his best, check out his classic album Soul Station.

After two choruses, you can hear Hank pause awkwardly at around 4:18, not deliberately like Miles, but out of uncertainty as to what to play next. He finishes his solo a little lamely too. These moments are a reminder that improvisation is an intrinsically risky undertaking. Any jazz soloist has to face to possibility of an unsatisfying improvisation, or even a complete trainwreck. The risk of failure (or incomplete success) is what makes jazz the exciting art form that it is.

Next comes Wynton Kelly’s piano solo, at 4:26. As in his intro, Wynton plays a lot of arpeggios, short chord fragments that call and respond to each other. Wynton was a veteran Miles Davis sideman by this point, and he sounds more relaxed and on his game than Hank Mobley. Wynton gets a chorus and a half, and at 5:24, Miles takes over, restating the second half of the melody. Next, there’s a short interlude, using the same pedal point as the intro. This reiteration of the head and intro in the middle of a recording is unusual. Miles is setting the stage for the tune’s dramatic climax, the entrance of John Coltrane.

A little back story: Coltrane had played tenor sax in Miles’ regular group on and off through the second half of the 1950s. Together, the two of them created some of the best and most famous recordings in jazz history, including Round About Midnight, Milestones, and Kind Of Blue. (Go buy them! You won’t regret it.) At the time of the “Prince” recording session, Coltrane had recently left Miles to lead his own staggeringly great band. But he happened to be visiting the studio that day, so Miles invited him to sit in.

What you’re hearing at 5:52 is Coltrane improvising with zero preparation, just sight-reading the chord chart. That may sound impressive, but it’s common for jazz musicians to enter a recording session unrehearsed. What you should be impressed by is the effortless intensity and power of Coltrane’s improvisation. His solo builds gradually, until by the start of the second chorus, he’s playing doubletime, cramming twice as many notes into each measure as the pulse of the tune would suggest. Coltrane’s lines twist and spiral with a complexity unmatched by anyone else in jazz at that time, and by few people since.

Coltrane had spectacular technique, but that isn’t the reason he’s so widely revered. What makes Coltrane so great is that his note choices all make emotional sense. Even when he’s playing fast, his lines have a rock-solid melodic structure to them. If you slow any Coltrane solo down, it becomes tuneful and even catchy. Any kid coming out of music school can play a lot of notes fast, but it’s rare to have those notes tell an emotionally compelling story. Nobody tells emotional stories like Coltrane. The “Prince” solo is just a taste of his firehose-like stream of ideas. Sadly, he died just six years after this recording was made.

After a short interlude, Miles plays the head out, the final statement of the melody. Usually the head out is identical to the head, but in this case, Miles just plays the first half of the form. Then there’s an outtro, much the same as the intro, a piano groove over the pedal point in the bass. Wynton Kelly plays more freely than he did on the intro, using darker and crunchier harmonies to match the intensity of Coltrane’s solo. Finally, the tune winds to a spontaneous close, by a hand signal or eye contact among the players. You can hear that Jimmy Cobb doesn’t quite land in the same spot as everyone else, he carries over a few extra beats. Then someone in the room makes a mysterious “pop” sound with their mouth, and the tune is over.

Most mainstream jazz recordings follow this same basic sequence of events, called the head-solos-head form. The band plays the melody, with or without an intro. Then different musicians play solos on the melody’s form. Finally, the whole band plays the melody again, and the tune ends. There are infinite variations on this basic structure. You can get a taste for them by listening to different versions of “Someday My Prince Will Come,” which has been recorded many times by jazz musicians over the years. Miles himself was inspired by Dave Brubeck’s 1957 recording, which is faster and doesn’t have the moody pedal-point interludes.

I chose this example because you’re likely to be at least somewhat familiar with the song. Jazz was easier to understand back in its heyday because it was based on well-known pop songs. If you went to hear Miles’ band perform in the 1950s, you would have recognized almost every tune they played. You would have been able to enjoy the difference between the conventional arrangement of a given tune and the intellectual abstractions that Miles applied. Now, unless you’re a showtune buff, you’re not likely to be familiar with most of the raw material that the jazz musicians are working with. No wonder people find jazz difficult or tedious.

Jazz musicians and fans can be snobbish toward pop music listeners, who are supposedly too unsophisticated to keep up with them. But we need to remember that in its prime, jazz was commercial music. Miles Davis had some legitimate jukebox hits with recordings that we now venerate as high art. When midcentury jazz musicians wrote their own tunes, they usually tried to make them as melodic and catchy as showtunes and popular standards. Miles’ own compositions of the late 50s and early 60s, like “So What” and “All Blues,” are as catchy and hooky as music gets.

If you want to listen to jazz now, and you don’t know a lot of pop standards and showtunes, the improvisation based on them will mostly just sound like random strings of notes. I had an easier time getting into the music through jazz originals like “So What” than through standards. Contemporary musicians are playing abstractions of abstractions of songs that were popular sixty, seventy or even eighty years ago. It’s left to the listener to supply all the historical context. The best way to approach the music now is to start on familiar territory. Find a tune you know and like, and check out how different artists approach it. Miles and Coltrane are great for this purpose, because they liked playing corny pop songs that are still in wide circulation, and because their interpretations are revelatory. Happy listening!