How do you listen to jazz for the most enjoyment? 
There are a variety of approaches, depending on the setting, the particular style of jazz, the listener's knowledge of jazz, and other factors.
In general, for beginners or advanced listeners, the best way to take in jazz, or any kind of music, is to listen in an open way, without much judgement or analysis, and experience the expression the performers are conveying. Feel the mood, happiness or sadness, lightness or darkness, no need to put into words or overthink what you're hearing and experiencing.
That being said, I'm going to attempt to “put into words” what can add to your knowledge and enjoyment in listening to jazz. There is a time and place for some analyzing, and I'm going to share some of my thoughts here without going too deep.
If you're listening in a live setting, what is the instrumentation? How many players? What instruments are more prominent, and what is the sound balance between instruments? Are the musicians looking at each other, and what are they trying to convey to each other? What is the main element of the music that catches your attention: loudness softness, or the contrasts? The beat: fast, slow, simple, complex? The song's opening melody: smooth, jagged, simple and catchy, or non-existent? What instrument or instruments give character to the performance: piano, guitar, horn, or a blend? What is the general harmonic, rhythmic, and melodic flow, and what does the performer's body language show? How does this all compare to live jazz you've heard in the past?
While listening to live jazz is best, there is a time-honored tradition in listening to recorded jazz. The Original Dixieland Jass Band first recorded in 1916! Until relatively recently, the only way to listen to a jazz recording was to play vinyl records on a turntable through a home stereo system. Now we have CDs, MP3 players, and streaming services such as Pandora and Spotify. We play music on YouTube through our iPhones. If we're lucky, we have quality speakers in our home or car. We may have voice-activated speakers such as Alexa that can instantly play almost any song or artist by voice command. Most of us would benefit by updating our music playback options, and I am doing research on this for my own upgrades. I will have more information on a future blog post!
If you're listening to recorded jazz, some of these same live-jazz issues apply, particularly instrumentation, rhythm, and melody. You can get deeply into analysis of the music or you may not analyze at all. You may recognize the song the musicians are playing, or it may be the first time you've heard it. You may be alone, or you may be with friends with the same intent of listening closely to the music. Or you may be in a random group while live or recorded music is playing in the background. Having jazz as background music is fine. However, I'm going to get into more specifics about what you can notice and enjoy by listening attentively to the music; specifically, what to listen for in jazz.
In preparing this article, I spent a lot of alone time listening to jazz which has given me the luxury of more detailed, attentive listening and reflection. I have to say that listening to great jazz recordings, spending more time at it than I usually do, has enhanced my awareness, heightened my mood, and raised my enthusiasm for great jazz and even for going to my gigs! I especially recommend this kind of listening or re-listening to jazz recordings you have loved in the past, and using YouTube and Google to discover new and old jazz recordings that you haven't heard before. What I'm presenting here, with this collection of links to great jazz recordings, is entirely subjective and reflects my personal tastes; but it is a list that includes recognized great artists and performances. I recommend that you return to this article as you listen piece by piece and eventually enjoy all these great recordings.
What is the starting point in listening to jazz? It may be helpful to state the basics. I've known even long-time jazz listeners who were unaware of the basic structure of a jazz performance.
In a typical performance of a jazz piece, the players will choose a song or composition with a melody and a harmonic structure or form. When the performance starts, you'll hear the melody the first time through the composition, then the form is continually repeated as the musicians take turns playing solos. The soloists improvise using the same form and harmonies. For instance, the song “Summertime” is a 16-bar (measure) song with four 4-bar phrases, a shortened ABAC song form. (The letters ABAC represent the form of the song only, not specific chords or keys.) After the song melody is played or sung, and possibly repeated, one musician will solo using the same form and the same harmonies but will improvise his own “melody.” Other instrumentalists (or a “scatting” vocalist—more on that later) will follow, each playing their own solos using the same 16-measure format, while the rest of the musicians accompany with the rhythm and harmonies according to the template defined by the opening melody.
You can hear an example of this with Miles Davis' 1958 recording of Summertime. He plays the 16-bar melody one time through and then improvises several times through. If you've already heard this recording in the past, it is worth re-listening. Beautiful accompaniment with horn arrangements by Gil Evans! If you're familiar with the song “Summertime,” you can follow Miles' improvisation more closely by inwardly (or outwardly) humming the melody along with his playing.
Miles Davis' - Summertime
One of the most popular jazz recordings of all time is Take Five by the Dave Brubeck Quartet from 1959. This piece, though very popular, is an anomaly, since it is in 5/4 time, an odd time signature for jazz. The song's composer, Paul Desmond, plays the melody line in a cool, natural, compelling way, and Dave Brubeck's rhythm section accompanies with a nice lilt. The song has a traditional 32-bar AABA form, and normally, a jazz performance would stay with that form for the improvisations. However, on this recording, Brubeck's quartet goes into a 2-chord “vamp” after stating the first chorus, essentially staying on the A section for the improvisations. Other performers since then have sometimes used the full 32-bar format for their improvisations.
Dave Brubeck Quartet – Take Five
Another very popular jazz piece is So What from Miles Davis' 1959 best-selling jazz album Kind of Blue. This piece is also an anomaly in that the “melody” is only a repetitive phrase played by the bass and answered each time by a horn riff. It is an AABA form, and the B section is the same as the A section only transposed up 1/2 step. Also, Miles Davis' use of atypical scales called “modes” was unusual for jazz at the time, but this has since come into wide acceptance. This recording includes a beautiful, haunting introduction written by pianist Bill Evans. There was a much faster-tempo 1964 version from the Steve Allen TV show with Miles, Herbie Hancock on piano, Wayne Shorter on sax. I watched this on live TV as a 15-year-old! (But can't find this version on YouTube anymore...)
Miles Davis - So What (from "Kind of Blue")
Miles Davis - So What (live)
Tenor saxophonist Ben Webster's 1944 recording of Irving Berlin's Blue Skies is less known but makes for delightful listening. This is an example of how jazz musicians take a pop tune of the day and use it as a vehicle for a jazz performance. The song is a familiar 32-bar AABA format. Ben Webster states the melody then takes one chorus (one time through the song) improvisation. The next chorus starts with a piano solo, with bass taking a short solo on the B section (B section is often called the “bridge.”) Ben improvises on the final chorus; the melody is not re-stated. The trio of piano, bass and drums provides a subtle, swinging accompaniment, and Ben propels the swing groove with his exuberant playing. 78 RPM limitations necessitates the shortness of this recording.
Ben Webster - Blues Skies
The 12-bar blues form is often used in jazz, and in some ways this is a blend of the categories of blues and jazz. The 1958 live video of the Dizzy Gillespie Quintet playing Blues After Dark, to me, falls squarely into the jazz category, though the “blues element” is in full force. (See my article The Difference Between Blues and Jazz.) The blues form can be used at a wide range of tempos, and this example is medium-slow, with bassist Ray Brown supporting an excellent groove. (For more on this swing groove, see my article Getting Into the Swing of Things.)
Dizzy Gillespie Quintet - Blues After Dark
The Gerald Wilson Big Band uses the blues form at a fast tempo in Nancy Jo from a 1962 recording. This is a recording I have enjoyed since my high school days, and I honestly hadn't analyzed it until now, which supports my theory that sometimes less analysis is better. I wasn't even consciously aware that this composition used a 12-bar blues form, partially because there is a 16-bar bridge or interlude injected later into the form of the piece. With Mel Lewis on drums this band really swings! Mel has said, “There isn't a better feeling in the world than swinging,” and Gerald Wilson's arrangements provide a great vehicle for these excellent, swinging musicians. A stellar moment in this recording is the tenor sax solo at 0:47. I'm not sure who he is, but he takes a short, soaring, solo on the fast-moving chord changes on the 16-bar bridge and makes it sound easy!
The Gerald Wilson Big Band - Nancy Jo
Other Jazz Recordings Using the 12-bar Blues Form:
Blues in C – Count Basie Trio (plus other guests)
That's All Right – Mose Allison Trio (with vocal)
Blues Monk - Thelonious Monk (solo piano)
Night Train – Oscar Peterson Trio
Vocal Jazz is in some ways its own category, or sub-category, of jazz. Sometimes (but not always) the jazz singer will sing a “scat chorus” after singing the words and melody, improvising as an instrumentalist would and using syllables that imitate a horn player.
In this recording of It Don't Mean a Thing If It Ain't Got That Swing, Louis Armstrong provides some scat singing after first stating the melody, including an opening “verse.” Duke Ellington is accompanying him on piano along with a rhythm section, plus trombone and clarinet. If I had to name my favorite male jazz singer (and there are a lot of good ones) it would be this guy.
It Don't Mean a Thing If It Ain't Got That Swing - Louis Armstrong
Ella Fitzgerald was known for her excellent scat singing, and her recording of Blue Skies, with big band accompaniment, is a classic. No wonder she is one of the most emulated female jazz singers.
Blues Skies – Ella Fitzgerald
Another approach to jazz singing, without “scatting,” is to alter the notes and the phrasing of the melody in an artistic way. Lorez Alexandria takes the familiar song Over the Rainbow and does her thing accompanied by the Wynton Kelly Trio. This approach is not to be entered into carelessly. For me, it's not normally pleasant to listen to singers who do not “honor the melody” at some point in a song's performance. In this recording, Lorez does not sing the octave jump on the first two notes of the chorus (“Some-where...”) which would normally be blasphemous! In spite of this, I love this recording and give her a pass because her control and artistry show that she could easily sing the straight melody if she wanted to.
Over the Rainbow - Lorez Alexandria
Here's a couple more random instrumental recordings that follow the same principles of a jazz performance, and they are fun to listen to:
Doxy - Miles Davis
Relaxed, swinging 1954 recording of this 16-bar trippy jazz melody based on the harmonic structure of the 1918 pop song Ja-da
Dickie's Dream - Count Basie Orchestra
Swinging, fast tempo, opening chorus uses simple riffs; all-star soloists include Lester Young, Gerry Mulligan, Roy Eldridge, and many others.
I hope that this information and playlist will give you a start in understanding, enjoying, and listening to jazz, or re-kindle a long-time interest. If you follow your attraction to particular artists and/or the types of pieces that you like, I have no doubt that you will find new territories and new joys!
Also, I hope listening to this list of mostly classic jazz recordings inspires you the same way it inspired me, and that spending time with this music will put you in a better place, a happier place, as it did for me!