I don’t think you have to (or even should) start with the canon, but here are ten albums that cover it without asking you to swallow a giant pill. They are in chronological order and (mostly) excluding the last 25 years, not because they aren’t full of wonders but because this is the canon.
Louis Armstrong – The Best of the Hot 5 & Hot 7 Recordings (late 1920s-early 1930s)
Louis Armstrong was the first and most important individual jazz star. He created a vocabulary for improvising on blues and other forms that remains essential. He also created a way of singing that may be the most vital influence in American music. This stuff sounds, 100 years later, old. But if you can hear beyond the recording quality and listen, it is all joy. Listen, at the same time, to the pre-jazz pop music of the 1920s and ‘30s and you will see that Armstrong was a revolution and a joy.
Duke Ellington – Never No Lament, The Blanton-Webster Band (late 1930s-1941)
Like Armstrong, Duke Ellington is a titanic figure in American music. His band and style of composing/arranging was one template for the “big bands” that became the popular music of that era. Here are some of his greatest compositions played by one of his finest bands.
Billie Holiday – The Essential Billie Holiday, The Columbia Years (late 1930s-1940s)
Billie Holiday took what she loved about the singing of Bessie Smith and Louis Armstrong, who preceded her. But she created an idiosyncratic style that was entirely her own – and much copied by all who came after her. She worked with many of the best swing-era musicians, and pianist Teddy Wilson and saxophonist Lester Young are stars on these sides as much as Holiday.
Charlie Parker – The Best of Savoy and Dial Studio Recordings (late 1940s)
Along with Dizzy Gillespie and Thelonious Monk, Charlie Parker expanded the sound of jazz by developing a new harmonic and rhythmic vocabulary that came to be called “bebop”. It doesn’t sound forbidding or weird today, but it is a dramatic expansion of what improvisers and composers could do with standard forms. The lines become more intricate and virtuosic. But “Bird” was always a brilliant blues player (“Parker’s Mood”), and his playing can take your breath away in a few different ways.
Miles Davis – Kind of Blue (1959)
This is famously the most popular jazz album of all time. Maybe it sounds today like some cliche of “jazz”, but it is a beautiful and profound document. Davis had a declarative style on trumpet, and most of these performances are so wonderful because they allow these distinctive musical personalities to play over “modes” instead of chords, encouraging a melodic but open style. The band includes all-stars John Coltrane (tenor sax), Cannonball Adderley (alto sax), Bill Evans (piano), Paul Chambers (bass), and Jimmy Cobb (drums).
Ornette Coleman – The Shape of Jazz to Come (1959)
This was called “free jazz” when it emerged at the tail end of the 1950s and into the 1960s because the playing was not as hemmed in by convention (a specific chord sequence or form, a defined tonal sound, unwavering 4/4 time) and, just like bebop 20 years earlier, it caught hell from traditionalists. Ornette Coleman plays the saxophone with a warm, vocal style and his songs are very melodic. “Lonely Woman” and “Peace” are appealing tunes. No piano or guitar so, yeah, the music sounds “free”.
John Coltrane – A Love Supreme (1964)
John Coltrane’s quartet played in the new “free” style at times, but they also showed how grounded that style was in truths of this music: blues, bebop, and jazz’s roots in older forms. This suite of four tunes is an incantation and an attempt to reach higher, spiritually, and in every other respect.
Wayne Shorter – Speak No Evil (1964)
Wayne Shorter was the tenor saxophonist for Miles Davis for most of this decade, and he wrote for that band. His records as a leader are just as good, and this one doesn’t have a single composition that is not formally daring yet appealing to the ear.
Herbie Hancock – Head Hunters (1973)
In the late 1960s, the next revolution in American music had fully arrived, and jazz players had no trouble finding ways to blend their art with the rock and soul music that was popular at the time. Miles Davis was at the forefront of this trend but he was hardly alone. This recording by Davis’s former pianist is a sophisticated blend of groove music and jazz. “Fusion,” like every jazz style, had many incarnations. This one still sounds like magic.
Mary Halvorson Octet – Away with You (2016)
Choosing a single recording to represent the New Jazz in the canon is nearly impossible, but this session represents almost everything that has mattered in recent decades: women are recognized as the equal of men in the art form, the electric guitar has become as creative and established as the saxophone or trumpet, “free” improvising is now effortlessly combined with intricate composition in the art, and the music continues to be thrilling. Is there pedal steel on this date? Is Mary Halvorson’s guitar shot through with wildly creative effects? Is the writing for brass riveting? Yes and yes and yes.