Jazz has always had an undeniable impact on culture, yet a tumultuous relationship with popular music. At one point in the middle of the 20th century, the genre was at the forefront. It had pop stars. Miles Davis, with his constant, sometimes puzzling musical innovation and penchant for performing with his back to the crowd, was the genre’s Kanye West. Wynton Marsalis, with his cocksure commitment to “pure music,” was an analogue to Dave Grohl. John Coltrane’s religious dabbling brings up Madonna.

Then, through the ’80s and ’90s, jazz seemed to lose direction, thanks in part to Kenny G, who let “jazz” mean music that’s more like bastardized adult contemporary pop-rock. Today, millennials are rediscovering the jams of jazz’s founding fathers, while contemporary artists are having their own small victories. The jazz star of today cannot compete with the likes of the modern pop star, but they still have their place. As a means of examining jazz’s rollercoaster trajectory — and calling out the names that solidified jazz’s importance in musical history — we’ve narrowed things down to one song at a time, demonstrative of the decade and the climate of jazz at the time.

1930s

“In the Mood” by the Glenn Miller Band

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Swing music bubbled up from the still-simmering Depression in the ’30s and skewed jazz closer than ever before to popular music. “In The Mood” is its enduring song. The Glen Miller Band had some modicum of success before “Mood,” but their breakthrough came in 1939 during a three-month stint at Glen Island Casino in New Rochelle, New York. Performances at the casino were broadcast to many via the radio, making Glen Island a springboard for numerous groups in the decade, though arguably none more than Miller. “The most important thing for Glenn’s success was that he recorded ‘In the Mood’ while he was at the casino,” biographer George T. Simon told The New York Times. “That made him the Michael Jackson of his day.”

The song is buoyed by its unmistakable opening sax riff, meant to beckon jitterbuggers to the dance floor, and highlighted by a mid-song decrescendo fake-out (think “Shout” by the Isley Brothers).

Bonus Fact: Jazz saxophonist Joe Garland, not Glenn Miller, actually composed the song, and the iconic opening lick may have been lifted from Wingy Manone’s 1930’s tune “Tar Paper Stomp.” Musicians played fast and loose with copyright laws in those days.

Perfectly Good Alternative: “Sing, Sing, Sing” by Bennie Goodman (1937)

1940s

“Round Midnight” by Thelonius Monk

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Bebop — musically complex and pioneered by players like Monk, Charlie Parker and Clifford Brown — was a swing on the pendulum from the simple music of the ’30s. Improvisation took flight, time signatures shifted, chords were voiced differently. Monk’s crawling, brooding “Round Midnight” embodies the shift well.

The song, with its plodding hi-hats, angular piano stabs and floating trumpet/sax harmonies is effortlessly complex and remains the most recorded jazz standard of all time. On listen, it brilliantly paints a picture of a dusky, stale bar at last call, and fittingly lasts a fleeting three minutes before screeching to a stop.

Bonus Fact: The standard is often credited with rebirthing Miles Davis’ career after the trumpet player’s struggles with drugs. Davis caught the ear of a Columbia Records scout while playing the tune alongside Monk at the 1955 Newport Jazz Festival.

Perfectly Good Alternative: “Yardbird Suite” by Charlie Parker (1946)

1950s

“Take Five” by Dave Brubeck

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Brubeck’s breezy, structured West Coast jazz came into vogue in the 1950s as an antidote to the abstractions of bebop. “Take Five,” the best-selling jazz single of all time, was an unlikely hit spurred by Brubeck’s visit to Turkey, where he heard street musicians experimenting with unorthodox time signatures. The final version of the song, with its signature 5/4 time and repeated piano vamp, was recorded in two takes and originally thought to be a throwaway.

Alto saxophonist Paul Desmond turns in a subtly great performance, but it’s rock solid drummer Joe Morello who showcases his mastery on the tune. His unwavering backbeat eventually cedes to a drum solo that is equal parts spacious and grooving, playfully gliding over the top of Brubeck’s piano line before kicking Desmond back in. The quartet would often close concerts with the song, leaving the stage one by one, until only Morello remained shredding the drums.

Bonus Fact: Jazz musicians fight with their record labels, too. Brubeck’s 1959 LP Time Out made Columbia nervous, with its original songs and abnormal time signatures. Label executives at Columbia, who preferred safe reworkings of old jazz standards, only agreed to release Time Out after the quartet recorded a more conventional album called Gone With The Wind to hedge their bet. Time Out went on to become the first jazz record to sell over a million copies.

Perfectly Good Alternative: “So What” by Miles Davis (1959)

1960s

“A Love Supreme, Part I (‘Acknowledgement’)” by John Coltrane

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Many songs are on this list because they’re the best embodiment of a decade’s sound — “A Love Supreme” makes it because it gleefully flew in the face of everything that was trending. In the ’60s, jazz was ceding its popularity to rock music and smooth, coasting bossa nova. Coltrane’s postbop epic “A Love Supreme” is abrasive and heady, full of avant-garde sensibilities and hinting at his free jazz future. The playing on the album is emotional and ponderous, born from the saxophonist’s recent Ahmadiyya Islam conversion and freshly sober outlook. In the liner notes, Coltrane wrote, “In the year of 1957, I experienced, by the grace of God, a spiritual awakening, which was to lead me to a richer, fuller, more productive life. Through the merciful hand of God, I do perceive and have been fully reinformed of his omnipotence. It is truly a love supreme.”

Bonus Fact: Before the unprecedented verbal chant in “Acknowledgement,” Coltrane plays the “Love Supreme” motif in all 12 keys on saxophone. “To me, he’s giving you a message here,” Lewis Porter, the head of jazz history at Rutgers University-Newark, told NPR. “First of all, he’s introduced the idea. He’s experimented with it. He’s improvised with it with great intensity. Now he’s saying it’s everywhere. It’s in all 12 keys. Anywhere you look, you’re going to find this ‘Love Supreme.’ He’s showing you that in a very conscious way on his saxophone.”

Perfectly Good Alternative: “Girl From Ipanema” by Stan Getz (1964)

1970s

“Chameleon” by Herbie Hancock

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That riff: 15 minutes, built on two chords, completely undeniable. “At a certain point I felt the need to play music that was more tethered, something that was more earthy,” Hancock told Uncut Magazine. “It was certainly a new approach for me. I didn’t realize that I was carving out new territory.”

Hancock, feeling inspired by contemporaries like Sly Stone and James Brown, fired his preexisting jazz sextet and gathered a backing band of funk musicians for the 1973 album that contained “Chameleon.” In an era where jazz was often muddled by electronics, rock ‘n’ roll and, to some extent, disco, this Hancock tune is remarkably pure and timeless. It manages to be a pop jazz hit while avoiding many of the trappings of that label.

Bonus Fact: That fat bass lick that anchors “Chameleon” was played by Hancock on an ARP Odyssey synthesizer.

Perfectly Good Alternative: “Pharaoh’s Dance” by Miles Davis (1970)

1980s

“Black Codes” by Wynton Marsalis

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The ’80s were the scene of the crime for smooth jazz, with Kenny G rising to popularity and his oft-lampooned downtempo, saxophone-driven songs gaining significant radio play. Simultaneously, wunderkind trumpet player and modern jazz’s prodigal son Wynton Marsalis aimed to regain respectability to the genre, trading the synth pads and programmed drum loops of Kenny G for the gliding polyrhythms and subtle swing that dominated 20 years before. Marsalis brashly criticized contemporary jazz, and when he earned a Grammy in 1984 he thanked “Charlie Parker, Thelonious Monk, Louis Armstrong — all the guys who gave an art form to the American people that cannot be limited by enforced trends or bad taste.”

On “Black Codes,” Marsalis was a purist playing neo-classics, expanding upon the bop style of ’60s-era Miles Davis. The tune is brimming with virtuosity and showcases the immense talent of each player in the quintet of jazz revivalists who called themselves “The Young Lions.” Some criticized Marsalis for merely recycling old styles, while others knocked him for perceived elitism. Jared Pauley, on Jazz.com, places this rebuttal: “Say what you want about Wynton Marsalis the person but Wynton Marsalis the trumpeter, especially during the 1980s, played with an assurance that I’ve hardly ever heard from any player since.”

Marsalis also found undying devotion from enigmatic jazz critic and poet Stanley Crouch, who would fill the liner notes of the trumpeter’s albums. “We are all lucky that such young musicians are playing jazz and handling its greatest demands with such an emotive sense of order,” Crouch wrote in Black Codes.

Bonus Fact: Pianist Kenny Kirkland and saxophonist Branford Marsalis (Wynton’s brother) quit the quintet shortly after the release of Black Codes from the Underground to join Sting’s band. Rumors of a feud trail the Marsalis brothers to this day.

Perfectly Good Alternative: “Quartet No. 1” by Chick Corea (1981)

1990s

“Let’s Fall In Love” by Diana Krall

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On “Let’s Fall In Love,” Diana Krall successfully negotiates the fine line between contemporary and jazz, proving to be a worthy descendant of Ella Fitzgerald and Billie Holiday. Yes, there is clean, legato guitar on this update of a classic that Fitzgerald once sang, but it’s vocal jazz more than smooth, pop jazz, and Krall proves to be a serious piano player, too. Some fans of the genre might challenge Krall as vanilla, but The New York Times‘ Ben Ratliff clarifies: “It’s gentle but firm,” he says. “Ready to negotiate with popular culture to be accepted through any possible doorway — as jazz, pop, cabaret, whatever.”

Bonus Fact: Krall’s 1999 album When I Look In Your Eyes, anchored by “Let’s Fall In Love,” was the first jazz album in 25 years to receive a Grammy nomination for Album of the Year.

Perfectly Good Alternative: “Jazz Thing” by Gang Starr (1990)

2000s

“Flim” by The Bad Plus

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There’s something really fascinating about a jazz trio energetically, effortlessly, and flawlessly covering an Aphex Twin song. The drums are the most notable challenge on “Flim,” with Bad Plus’s Dave King smacking out a live replication of the inhuman, flanged-out electronic beat, and the result is spritely and glitchy, like an unplugged take on The Postal Service, but as jazz. “The fact that most everybody in the stratified jazz world was talking about this record circa 2003 is evidence enough of its importance,” wrote Patrick Jarrenwattananon for NPR. “The fact that it got people outside ‘jazz’ to listen was the real coup, though.”

Bonus Fact: The trio garnered much notoriety for their cover of Nirvana’s “Smells Like Teen Spirit,” a tune which pianist Ethan Iverson claimed to have never heard before.

Perfectly Good Alternative: “Paranoid Android” by Brad Meldhau (2002)

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