Reid Miles designed nearly 500 jazz album covers, establishing a unique aesthetic for the genre in the 1950s and '60s.

Miles Davis might be the most recognizable name in jazz history, renowned for his landmark albums "Kind of Blue" and "Bitches Brew," and his unceasing artistic experimentation. By the 1980s, however, Davis was a pariah in jazz circles, causing him to set his sights on the poster child for the genre's purists: the much younger Wynton Marsalis. This overview of the rivalry by journalist James Kaplan details the origins—and the apex—of this now legendary beef.

Davis was an adept bebop trumpet player, but he grew tired of the style. With 1959's "Kind of Blue," he pioneered a new style of jazz, called modal jazz, that focused less on improvising on chord progressions and more on open, tone-based expression.

The album is one of jazz's best-known recordings and is often listed among the greatest albums of all time, of any genre. Despite its monumental impact, it was recorded in two sessions for just a few thousand dollars.

The prolific artist loved music, obsessing over David Bowie, Aretha Franklin, and numerous jazz figures. Many of his favorites appeared in his paintings, creating a body of work that also acts as a glossary of influences. Below is a 1984 portrait of Max Roach, the jazz drummer.

The pianist and arranger was one of the genre's biggest names in the early 20th century, though very few believed him when he claimed he had invented the music in 1902. One of his biggest contributions to the genre was a 1938 session with ethnomusicologist Alan Lomax, who recorded nearly 8 hours of music and stories that have become an essential part of the music's history.

The Great Migration transformed New York City's Harlem neighborhood into the epicenter of Black American art, with artists such as Duke Ellington, Louis Armstrong, and Bessie Smith regularly performing. The music not only provided the backbeat to the cultural scene—it often influenced it, with Harlem Renaissance poets, in particular, inspired by jazz's approach to rhythm and improvisation.

Ornette Coleman's 1959 album "The Shape of Jazz to Come" abandoned traditional notions of melody and structure, inadvertently creating "free jazz," a subgenre that embraced absolute musical freedom and gained popularity in the countercultural 1960s.

Diving into the history of jazz can be intimidating, but this list is a helpful guide, highlighting the best of the best, with titanic recordings from Louis Armstrong, Billie Holiday, Miles Davis, Dave Brubeck, Alice Coltrane, Oscar Peterson, and more.

As jazz entered the '70s, it was at a crossroads. While the genre's figureheads explored fusion and free jazz, which intentionally flouted mainstream convention, other artists began veering towards pop. Eventually, that sound would be called "smooth jazz."

- Miles Davis (1926-1991)

Songs like Billie Holiday's "Strange Fruit," which portrayed the grim brutality of lynching, and John Coltrane's "Alabama," which was modeled on the rhythm of a speech by Martin Luther King Jr., were the backbeat of the movement.

The scale and reach of Picasso and cubism inspired artists and art movements throughout the early to mid-20th century. In fact, his influence can still be seen in artists today. One such artist, George Condo (known for painting the album cover of Kanye West’s “My Beautiful Dark Twisted Fantasy,” pictured below), heavily references Picasso’s visual language, transmuting the legendary artist’s geometric shapes and perspectives for a more contemporary audience.

First editions of Burroughs’s "The Naked Lunch," Kerouac’s "The Dharma Bums," and Ferlinghetti’s "A Coney Island of the Mind" were just as notable for their text as they were for their design, which anticipated the psychedelic imagery of 1960s countercultural touchstones like Ken Kesey, Andy Warhol, and R. Crumb.

Singer and bandleader Cab Calloway was a major figure in the Harlem Renaissance's music scene. He was also one of the biggest names in jazz's swing era and would go on to be the first Black American to have a nationally syndicated radio show and the first to sell a million copies of a record. In this 1934 short film, "Cab Calloway's Hi-De-Ho," he reenacts his upbeat performances at Harlem's Cotton Club.

Although jazz was once a popular art form, it has largely been confined to the margins of pop culture, with many of the genre's current bestselling albums from previous decades. Some critics argue that this is because the music betrayed its position as dance music and focused instead on musical proficiency.

The jazz style took off in the 1940s, mesmerizing listeners with its wild, improvised solos. It had a particular impact on the writers of the Beat Generation, including Jack Kerouac and Allen Ginsberg, who saw in bebop's freedom a model for what they could achieve through the written word. Beat writers like Lawrence Ferlighetti and Kenneth Rexroth even incorporated live jazz in their poetry readings.

Similar to blues, folk, and country music, jazz relies on a shared tradition of common songs that its artists learn, cover, and rework in their own unique ways. Jazz musicians are often able to easily improvise with other musicians because they share a knowledge of the songs and their languages.

Douglas learned about Harlem's cultural scene while teaching high school in Kansas City and was eventually recruited to New York by Charles S. Johnson, the editor of the National Urban League's periodical. Soon, Douglas was illustrating periodicals and books affiliated with the movement. In 1934, the Works Progress Administration commissioned him to paint the "Aspects of Negro Life" murals. One of those murals, "Song of the Towers," pictured below, portrays Black life during the Harlem Renaissance.

Poets like Walt Whitman and Claude McKay inspired Hughes, but he was also enamored with blues and jazz music. The styles informed the way he structured his verses, with Hughes employing repetition and rhythm in ways similar to the standard 12-bar blues form and playing with meter in a way that recalled the improvisation of jazz.

Like his graffiti, Basquiat’s drawings and paintings often featured words and phrases among images. Art historian Robert Farris Thompson said, “[i]t’s as if he were dripping letters.” Below is 1983’s Horn Players, which includes portraits of jazz greats Charlie Parker and Dizzy Gillespie, along with words Basquiat associated with them.

The 1962 album by Stan Getz and Charlie Byrd was an unexpected hit, reaching the top of the Billboard album chart and receiving a Grammy nomination for album of the year. Its lead single, "Desafinado," won the Grammy for best jazz performance and is now considered one of the genre's classic tracks.

When jazz exploded in the 1920s, some believed the music's sudden popularity was the sign of a rotten nation, with one 1920 address at the University of Wisconsin proclaiming, "We are in deadly fear of the Jazz Devil, the demon which is consuming the country." Often, the connections were racialized, with columnists and preachers suggesting that jazz's Black artists were attempting to degrade white America.

Hip-hop was born out of obscure samples, including many that were taken from the annals of jazz. That style was especially popular in rap's early eras, with the subgenre "jazz rap" becoming an accurate descriptor for New York groups like A Tribe Called Quest and Gangstarr.

The 1964 bossa nova classic won the Grammy for album of the year, a rare feat for a jazz record. According to jazz pianists Peter Martin and Adam Maness, that also makes it one of the last truly popular jazz albums. In this episode of their podcast "You'll Hear It," they break down the musicality of the songs in real time, offering technical insights into every quirk and nuance.

Released in the midst of the Civil Rights Movement, Charles’ records showed that country music, by then largely segregated, was an American music, no matter one’s background.

Glaser was famous for creating the "I Heart NY" logo, the DC Comics logo, and an iconic Bob Dylan poster for CBS Records, but he naturally transitioned to illustrating children's books like "The Smallest Elephant in the World" and "If Apples had Teeth." Carle, author of "The Very Hungry Caterpillar" and "Brown Bear, Brown Bear, What Do You See?," began his career in advertising. Scholars say mid-century modern's preference for clean lines and bold colors was a natural fit for kids' books.

The essay, delivered in 1956 at the Newport Jazz Festival, offers a poetic take on defining jazz, suggesting that it is the root of both literature and music. “Jazz is a great big sea,” he says. “It washes up all kinds of fish and shells and spume and waves with a steady old beat, or off-beat.”

Jazz began in 19th-century New Orleans, though its roots go back even further. This timeline situates the music's evolution alongside American and world history, offering an illuminating exploration of the genre.

Inspired by eclectic artists like Sly and the Family Stone, as well as lesser-known mentors and peers in the Twin Cities, Prince blended R&B, rock, pop, new wave, soul, funk, punk, and more, creating a sound that defied easy categorization.

The 20th-century movement sought to develop a universal language for the modern era by fusing form and function. Modern day viewers will recognize its bright colors and clean aesthetic, popular with retro-styled book and album covers.

Ragtime was a popular music genre that blended African-American spirituals, European folk songs, and military marches. Blues, brought to New Orleans by free Black people seeking opportunities, allowed musicians to play within basic standards. Jazz combined both forms by merging the syncopated, dance-friendly sounds of ragtime with the soulful, brass-instrumental style of the blues.

The 1917 song by the Original Dixieland Jass Band was the first jazz recording to be issued and put the New Orleans sound on the national stage, along with inspiring several soundalikes.

1958’s “The Weary Blues” features Hughes reciting poems over jazz. The back half of the album is accompanied by bassist Charles Mingus and his ensemble, just a year before Mingus would release his landmark record “Mingus Ah Um.”

In 1942, the publication introduced the Harlem Hit Parade chart, listing the top 10 records sold at select record stores in the majority-Black borough of New York. In 1945, it changed the chart’s name to Most Played Juke Box Race Records, using the music industry term (“race record”) that identified recordings by Black artists, even if they played music markedly similar to the white artists on the other charts.

The style is when a musician plays a rhythm on the opposite side of the beat. That means notes are played on the "upbeats," or the spaces between the main beats of a musical bar. The effect is music that can sound unpredictable, even if it's been carefully constructed.

The iconic artist had a short career, but he produced a massive body of work and changed the style of American art by bringing together pop art, graffiti, hip-hop, and punk. His work still hangs in galleries across the world. View scans of the most famous ones here.

The 1957 CBS special, part of its series "The Seven Lively Arts," was a landmark broadcast that brought some of jazz's biggest names—including Holiday, Thelonious Monk, and Count Basie—to a national audience. Watch Holiday offer a stirring rendition of "Fine and Mellow" below.

Both Picasso and Basquiat are major figures of 20th-century art, with distinctive styles that flew in the face of the formalized standards of their respective times. Below is one of Basquiat's portraits of Picasso, who influenced the younger artist’s approach to form, from 1984.

The large-scale migration of Black Americans looking to escape Jim Crow laws in the South began in 1915 and helped bring New Orleans music to other parts of the country, including Chicago, New York, Kansas City, Detroit, and Los Angeles.

While jazz musicians are known for their improvisational skills, they rely on years of training and a complex understanding of compositions to inform their improvised solos, using a song's structure and chords to make their in-the-moment choices. Although jazz artists could, in theory, play whatever they wanted, musicians often employ common melodic approaches—such as scalar improvisation and arpeggios—to generate solos.

The son of two Minneapolis jazz musicians, Prince was surrounded by music from a young age. His full name, Prince Rogers, was actually derived from his father's group, the Prince Rogers Trio. He eventually learned how to play his father's piano, teaching himself the themes to popular TV shows. Eventually, he learned other instruments and expanded his music tastes, indulging in records by Sly and the Family Stone, Jimi Hendrix, Joni Mitchell, and more. Below is his junior high school yearbook photo.