In December of 1965, having just finished their first full-length studio album together, E.S.P., Miles Davis’s second great quintet—including Wayne Shorter, Herbie Hancock, bassist Ron Carter, and a young drumming firebrand named Tony Williams—prepped for a gig at Chicago’s Plugged Nickel. Oddly, the sets they played over the course of their two-night engagement contained none of the original music the group had just recorded, and instead consisted entirely of standards that had been in Davis’s live repertoire for many years.
 
The eccentric treatments the group committed to tape over those seven sets were apparently the results of a dare: Prior to the gig, according to Shorter’s biographer Michelle Mercer, Williams challenged his bandmates to “break free of their accustomed musical ideas and techniques” and try instead to play “anti-music.” Thus did the quintet arrive at a frenzied double-time version of “So What”—which first appeared as the lead-off track for Kind of Blue, Davis’s inescapable quintuple-platinum hit record.
 
“So What” as Davis’s sextet recorded it in 1959 is perhaps the most immediately recognizable jazz tune. From the melodic theme, delivered not by the horn players as one would expect but instead by bassist Paul Chambers, to pianist Bill Evans’s chord voicings—so distinctive that some critics have taken to calling them the “So What chords”—the song in its original form seduces the listener despite the bandleader's eccentric arranging choices.
 
The second great quintet’s version, by contrast, is hilariously irreverent: The band races headlong through the changes, slurring the melodic theme, crashing from solo to solo, and playing with a ferocity that likely pleased their leader given that within a year or two he would begin referring to his immortal ‘50s outing as “warmed-over turkey.”
 
Heading into the second half of the ‘60s, Miles was ready to discard all of his previous notions of jazz and occupy new sonic territory—and he’d clearly found the group of young musicians to take him there.

In 1959, at the age of 26, Wayne Shorter joined Art Blakey’s Jazz Messengers. Over the next four years, the young tenor sax player became indispensable as the band’s musical director and primary composer. Shorter would go on to write a number of enduring standards and help change the direction of jazz not once but twice—first with Miles Davis’s Second Great Quintet, which came to define post-bop and presaged the shift to fusion; then with keyboard player Joe Zawinul in the band Weather Report through the ‘70s, taking elements of funk, world music, and electronically processed sounds into rock arenas worldwide.
 
Here, in a stripped-down quartet, with sympathetic backing on piano from frequent collaborator Herbie Hancock, Shorter demonstrates how simple or familiar structures—in this case, a 12-bar blues, albeit one mostly set in elliptical-sounding 6/8 time—could offer space for players to develop brooding abstract moods and textures. Shorter and Hancock would go on to record this composition again a year later on an album with Davis, who arguably opened the door for these types of sounds in 1958 with his pioneering modal jazz album Kind of Blue.

Tenor sax player Joe Henderson is often thought of as a gifted journeyman musician, fitting himself to a variety of settings and projects. From 1963 to 1968, Henderson appeared on a whopping 30 albums for Blue Note records—from pianist and founding Jazz Messenger Horace Silver’s classic bossa nova-tinged hard bop album, Song for My Father (1965), to composer Andrew Hill’s intense, eccentric, thoroughly modern debut, Black Fire (1964).
 
But Henderson was an important modern jazz voice in his own right, both for his compositions—many of which became standards—and for his distinctive approach to soloing. In his songs, Henderson relied on traditional forms like the 12-bar blues, but always included unusual chord changes and harmonic surprises. His playing was similarly rooted in bebop traditions, but full of idiosyncratic expressive choices, particularly in his instrument’s upper altissimo register.
 
Mode for Joe was Henderson’s last date as a bandleader for Blue Note records in this decade, and it highlights both the saxophonist’s distinctive yet malleable voice and his position hovering between hard- and post-bop, old music and new. Pianist Cedar Walton composed this title track, and it serves as a showcase for fine extended playing from vibraphonist Bobby Hutcherson and trumpeter Lee Morgan, but it’s Henderson’s schizophrenic opening solo—at turns melodic, bluesy, honking with overtones, and atonally sideways—that commands attention.

​Producer Bob Thiele really, really, really did not want tenor sax player Archie Shepp on Impulse Records—but Impulse superstar John Coltrane insisted that he deserved a shot. Thus did Thiele eventually arrive at a compromise: Shepp could record an album for his label, but all of the tunes would have to be Coltrane’s, and the marketing would emphasize the star connection.
 
The resulting album, Four for Trane, effectively linked the old guard to the new—and offered unusual takes on three Coltrane compositions from Giant Steps (1960) and one from Coltrane Plays the Blues (1962). Part of the credit for the album’s excellence goes to trombonist and arranger Roswell Rudd; part to a rhythm section featuring former Coltrane and Ornette Coleman collaborators. But the star, of course, is Shepp, whose playing here feels fluid and unforced—despite his angular lines, growling tone, and frequent squealing forays past the upper reaches of his instrument’s natural range.
 
The following year, Shepp would share a live album with his mentor and label-mate: New Thing at Newport, which documented Shepp and Coltrane playing separate sets at the Newport Jazz Festival on July 2, 1965. That same summer, he also appeared on Ascension (1965), Coltrane’s roaring big band free jazz experiment, featuring two bassists, seven horn players, and one single extended track, split across two album sides. “The ensemble passages were based on chords,” Shepp later recalled, “but the chords were optional…there is a definite tonal center, like a B-flat minor. But there are different roads to that center.”
 
Ascension divided jazz critics and made clear that Coltrane was allying himself with a new generation of players like Shepp; the session would mark the beginning of the end for Coltrane’s classic quartet.

​During the 1940s, Art Blakey played drums in a number of popular groups, including the Fletcher Henderson Orchestra and Billy Eckstine’s big band. Blakey was in demand as a hard-swinging timekeeper, favoring dance rhythms undergirded by hi-hat pedal stomping and locked-in, unwavering tempos.
 
His true importance, though, lay in his abilities as a bandleader. Beginning in 1955, he co-led a quintet that appeared on their Blue Note debut as Horace Silver and the Jazz Messengers; by the time the group recorded a pair of live albums at the Café Bohemia that November, the name at the top of the bill was Blakey’s. Silver left the following year, but Blakey would continue to record under that moniker as the sole original band member for more than three decades, serving as a mentor for generations of players.
 
By the time of Free for All, Blakey had already gone through three band lineups. This fresh bunch of Messengers included young lions Wayne Shorter on tenor saxophone and Freddie Hubbard on trumpet; their energy no doubt inspires Blakey’s aggressive attack and non-stop soloing here. Shorter wrote this tune; his composing and playing are the epitome of post-bop, a type of semi-traditional jazz that emphasizes original compositions, loose attitudes towards rhythm and song structure, and abstract-sounding approaches to soloing.

Nowadays vibraphonist Roy Ayers is indelibly linked with funk and disco: His group The Roy Ayers Ubiquity recorded the soundtrack for the blaxploitation movie Coffy and scored top ten Billboard hits with albums Everybody Loves the Sunshine (1976) and Lifeline (1977). In 1979, after three weeks of touring in Nigeria, Ayers even recorded an album with Afro-funk pioneer Fela Kuti and his Africa 70—delivering two extended, repetitive jams, each the full length of an LP side. On the record, both bandleaders sing futuristic messages imagining worldwide Black unity by the year 2000.
 
Yet Ayers began his career as a traditional jazz player. In the 1950s, the Los Angeles native studied with his soon-to-be-famous vibraphonist neighbor, prolific Blue Note recording artist Bobby Hutcherson; in the ‘60s, he played in flautist Herbie Mann’s group, recording a series of accessible albums that drew together soul jazz, middle eastern sounds, and covers of pop hits by the Beatles and Sonny Bono.
 
Ayers’s 1967 album as a post-bop bandleader, Virgo Vibes, showcased his ability to play with tempos, textures, and phrasing. Lead-off track “The Ringer” feels complex despite being built on only three chords—and allows a group including tenor sax player Joe Henderson and pianist “Ronnie Clark” (Herbie Hancock under an assumed name) to stretch out as they please.

​Like Grant Green, Hank Mobley was most firmly associated with hard bop and soul jazz. His 1960 album for Blue Note, Soul Station, is generally regarded as his high point as tenor saxophonist and bandleader—not a groundbreaking album, but nonetheless one of those hard-swinging, delectable records that everyone interested in jazz probably ought to own. It highlights Mobley’s signature “round” tone—warm and inviting yet free of stage-y affectations.
 
In the 1950s, Mobley made the rounds, playing with trumpeter Dizzy Gillespie, drummer Max Roach, and as a founding member of the Jazz Messengers with Art Blakey and Horace Silver. In 1961, he replaced John Coltrane in Miles Davis’s quintet, but left within a year, frustrated by a band in transition—and possibly unable to fill Coltrane’s outsized shoes. “When I left Miles,” he explained in a 1973 interview, “I was so tired of music, the whole world, man, I just went back to drugs.”
 
In 1964, Mobley was arrested for heroin possession; throughout the prison stint that followed, he refocused and wrote a slew of ambitious new tunes, many of which would be recorded in 1966 for A Slice of the Top. The album brings together a curious yet potent assortment of sounds: Mobley arranged it with pianist Duke Pearson for an octet, and it features parts for both tuba and euphonium. Players included trumpeter Lee Morgan, who had been a member of the third incarnation of Art Blakey’s Jazz Messengers in the late ‘50s; pianist McCoy Tyner, known for his pyrotechnics in Coltrane’s A Love Supreme-era classic quartet; and alto sax player and Sun Ra Arkestra veteran James Spaulding.
 
Mobley considered it his finest album—yet sadly it wasn’t released until more than a decade later, in 1979. As Mobley explained in the same interview: “I have about five records on the shelf—Blue Note had half the black musicians around New York City, and now the records are just lying around. What they do is just hold it and wait for you to die.”

​Grant Green was known as a traditional hard bop and soul jazz player; his records took a turn toward extra amplification at the end of the ‘60s, but he was otherwise remarkably consistent in his choices. Aside from the occasional detour into bossa nova (see The Latin Bit, recorded with Afro-Cuban Jazz drummer Willie Bobo and including the sounds of congas and chekere) his playing style throughout his career remained steeped in blues and R&B. He treated guitar as a lead instrument, eschewing chords and preferring single-note melodic lines—possibly because his main influences were not guitarists but horn players, including Charlie Parker, Miles Davis, and Joe Henderson.
 
Green was a mainstay for Blue Note records, recording more than 20 albums as a bandleader from 1961–65 and many more as a sideman, appearing in sessions with Hank Mobley, Herbie Hancock, and McCoy Tyner. Yet despite his prodigious output and distinctive phrasing, Green was largely underappreciated during his lifetime and generally regarded as a utility player, not a star.
 
"Grantstand" is the title track for an album recorded for Blue Note in 1961 and released the following year. It’s the earliest recording in this mix, and it demonstrates how players coming out of the 1950s hard bop scene brought other forms of dance-oriented music into jazz. Not only that: With the popularity of R&B organ trios in the late 1950s and early ‘60s, and the prolific recorded output of organists like Jimmy Smith and Shirley Scott, jazz sessions routinely included electrified instruments—in this case, “Brother” Jack McDuff’s Hammond B3—long before “going electric” became a cause for alarm among some music purists.

​This mix follows overlapping generations of musicians as they navigated divergent threads in jazz from 1962 to 1972—a decade of rapid stylistic change. During this time, players looked to their roots in traditional blues and R&B; to the hypnotic sounds of powerfully amplified funk and acid rock; and to non-western instruments, spiritual awakenings, and radical ideologies, pushing past the expectations of the record-buying public and forging new tools for reinvention and self-discovery.
 
By the end of this decade, “avant-garde” in jazz could mean either a populist embrace of the zeitgeist or a withdrawal to rarefied spheres in which most of the familiar elements of musical composition were discarded. For Miles Davis, it meant gathering an expanded percussive ensemble and recording droning, elliptical funk grooves; for John Coltrane, it meant recruiting younger players willing to abandon conventional tonality or timekeeping and follow him into the unknown.
 
This split mirrors attitudes toward audiences in other modernist circles. In his book The Rest Is Noise, critic Alex Ross describes how avant-garde classical musicians in early twentieth century Europe engaged in “an easy back-and-forth between occult esotericism and cabaret populism.” In Paris, he explains, composers moved “into the brightly-lit world of daily life;” in Vienna, meanwhile, musical iconoclasts were busy “illuminating the terrible depths with their holy torches.”
 
Traditionalists like critic Stanley Crouch have tended to regard this decade as the art form’s denouement. He essentially defines jazz as repertory music—the development of which begins with Louis Armstrong’s Hot 5 and Hot 7 recordings in the 1920s; continues through the varied career of Duke Ellington, the rise and fall of big bands, and bebop in the 1950s; and ends with John Coltrane’s mold-breaking 1964 album, A Love Supreme.
 
For Crouch, the music that came after—free jazz, fusion, and other avant-garde explorations—hardly merits consideration. "We should laugh at those who make artistic claims for fusion," he opined in a 2003 article for Jazz Times.
 
Crouch has championed a generation of neo-bop players determined to turn the cultural clock back to the mid-1950s—like, for example, the Marsalis family. In an interview for the 2001 Ken Burns PBS documentary series, Jazz, saxophonist and composer Branford Marsalis echoes Crouch, referring to the albums of avant-garde pianist Cecil Taylor as “self-indulgent bullshit,” and summing up the 1970s by saying “jazz just kind of died. It just kind of went away for awhile.”
 
While these ideas have metastasized in parts of the cultural establishment, the classicist redefinition of jazz as a closed system—a story with one central through-line, possessing a beginning, middle, and definite end—ignores the non-linear messiness of how musicians actually work together, trading ideas in real time and creating new music out of the ashes of the old, session-by-session, gig-by-gig. In fact, the divides between free jazz and fusion—or even rock, jazz, and classical music—are far from absolute: Coltrane embraced the sounds of both Igor Stravinsky and Babatunde Olatunji; Miles Davis studied Karlheinz Stockhausen and saw proto-punk band The Stooges play in concert. A simplified narrative that ignores social context and dismisses years of complex human creativity and expression should immediately make us suspicious—and, hopefully, curious to hear more.