Kassa Overall is tired of talking about the connections between jazz and rap. He had to do it when he released his last two albums, and he has to do it again regarding his latest one.

"They go together naturally," he once said. "They're from the same tree as far as where they come from, which is Black music in America. You don't have to over-mix them. It goes together already."

Expand this outward, and it applies to all Black American musics; it's not a stretch to connect gospel and blues, nor soul and R&B. Accordingly, jazz and rap contain much of the same DNA — from their rhythmic complexity to its improvisational component to its emphasis on the performer's personality.

Whether in sampling, the rhythmic backbone, or any number of other facets, jazz and rap have always been simpatico; just watch this video of the ‘40s and ‘50s vocal group the Jubilaries, which is billed as the “first rap song” and is currently circling TikTok. And as Overall points out to GRAMMY.com, even jazz greats like Louis Armstrong or Dizzy Gillespie had “Lil B and Danny Brown energy.”

From A Tribe Called Quest to the Roots to Kendrick Lamar, rap history is rife with classics that intertwine the languages of two Black American artforms. Here are 10 of them.

De La Soul — 3 Feet High and Rising (1989)

GRAMMY-winning Long Island legends De La Soul's catalog is finally on streaming; now's the perfect time to revisit these pivotal jazz-rap intersecters. 

Featuring samples by everyone from Johnny Cash to Hall and Oates to the Turtles, their playful, iridescent, psychedelic 1989 debut, 3 Feet High and Rising, is the perfect portal to who Robert Christgau called "radically unlike any rap you or anybody else has ever heard,"

3 Feet High and Rising consistently ranks on lists of the greatest hip-hop albums of all time. In 2010, the Library of Congress added it to the National Recording Registry.

A Tribe Called Quest — The Low End Theory (1991)

If one were to itemize the most prodigious jazz-rap acts, four-time GRAMMY nominees A Tribe Called Quest belong near the top of the list. Their unforgettable tunes; intricate, genre-blending approach; and Afrocentric POV, put them at the forefront of jazz-rap.

There are several worthy gateways to the legendary discography of Q-Tip, Phife Dawg, Ali Shaheed Muhammad, and Jarobi White,, like 1993's Midnight Marauders and 1996's Beats, Rhymes and Life. 

But their 1991 album The Low End Theory, was a consolidation and a watershed. From "Buggin' Out" to "Check the "Rhime" to "Scenario" — featuring Busta Rhymes, Charlie Brown and Dinco D — The Low End Theory contains the essence of Tribe’s vibrant, inventive personality.

Plus, it's not for nothing that they enlisted three-time GRAMMY winner Ron Carter to play on The Low End Theory; he's the most recorded jazz bassist in history.

Dream Warriors — And Now the Legacy Begins (1991)

Representing Canada are Dream Warriors, whose And Now the Legacy Begins was a landmark for alternative hip-hop. 

King Lou and Capital Q's 1991 debut eschewed tough-guy posturing in favor of potent imagination and playful wit. Christgau nailed it once again with his characterization: "West Indian daisy age from boogie-down Toronto."

Its single "My Definition of a Boombastic Jazz Style" samples "Soul Bossa Nova" by 28-time GRAMMY winner Quincy Jones — who, among all the other components of his legacy, is one of jazz's finest arrangers. The tune would go on to become the Austin Powers theme song; in that regard, too, Dream Warriors were ahead of their time.

The Pharcyde — Bizarre Ride II the Pharcyde (1992)

All of Black American music was fair game to producer J-Swift; on the Pharcyde's classic debut Bizarre Ride II the Pharcyde, he sampled jazzers like Donald Byrd and Roy Ayers alongside Marvin Gaye, Jimi Hendrix, Sly and the Family Stone, and more. Over these beds of music, Fatlip, SlimKid 3, Imani, and Bootie Brown spit comedic bars with blue humor aplenty.

"I'm so slick that they need to call me, "Grease"/ 'Cause I slips and I slides When I rides on the beast" Imani raps in "Oh S—," in a representative moment. "Imani and your mom, sittin' in a tree/ K-I-S-S (I-N-G)."

All in all, the madcap, infectious Bizarre Ride II the Pharcyde is a pivotal entry in the jazz-rap pantheon. One reviewer put it best: "[It] reaffirms every positive stereotype you've ever heard about hip-hop while simultaneously exploding every negative myth."

Digable Planets — Reachin' (A New Refutation of Time and Space) (1993)

Digable Planets' Ishmael Butler once chalked up the prevalent jazz samples on their debut as such: "I just went and got the records that I had around me," he said. "And a lot of those were my dad's s—. which was lots of jazz." It fits Digable Planets like a glove.

"Rebirth of Slick (Cool Like Dat)" contains multiple elements of Art Blakey and the Jazz Messengers' "Stretching"; "Escapism (Gettin' Free" incorporates the hook from Herbie Hancock's "Watermelon Man"; and "It's Good to Be Here" samples Grant Green's "Samba de Orpheus. Throughout Reachin', Butler, Craig Irving and Mary Ann Viera proselytize Black liberation in a multiplicity of forms.

Pitchfork nailed it when it declared, "​​Reachin' is an album about freedom — from convention, from oppression, from the limits imposed by the space-time continuum."

Gang Starr — Daily Operation (1992)

In the realm of Gang Starr, spiritual consciousness and street poetry coalesce. Given that jazz trucks in both concepts, it's a natural ingredient for DJ Premier and Guru's finest work.

One of their first masterpieces, Daily Operation, contains some of jazz's greatest minds within its grooves. "The Place Where We Dwell" samples the Cannonball Adderley Quintet's "Fun"; Charles Mingus' "II B.S" is on "I'm the Man"; the late piano magician Ahmad Jamal's "Ghetto Child" pops up on "The Illest Brother." 

Throughout their career, DJ Premier and Guru only honed their relaxed chemistry; jazz elements help give their music a natural swing and sway. (Their musical partnership continues to this day; Gang Starr is releasing music this very week.)

The Roots — Things Fall Apart (1999)

Three-time GRAMMY winners The Roots' genius blend of live instrumentation and conscious bars launched them far past any "jazz-rap" conversation and into mainstream culture, via their role as the house band on "The Tonight Show Starring Jimmy Fallon."

Elements of limbic, angular jazz can be found throughout their discography, but their major label debut Do You Want More?!!!??! might be the most effective entryway into their blend of jazz and rap. ("Silent Treatment" features a bona fide jazz singer as a guest, Cassandra Wilson.)

Whether it’s the burbling "Distortion to Static," or the jazz-fusion-y "I Remain Calm," or the knockabout "Essaywhuman?!!!??!", venture forth into the Roots' discography; they're a hub of so many spokes of Black American music.

Madlib — Shades of Blue (2003)

As jazz-rap connections go, Madlib's Shades of Blue is one of the most pointed and direct.

Therein, he raids the Blue Note Records vault and remixes luminaries from Wayne Shorter ("Footprints") to Bobby Hutcherson ("Montara") to Ronnie Foster ("Mystic Brew," flipped into "Mystic Bounce"). In the medley "Peace/Dolphin Dance," Horace Silver and Herbie Hencock's titular works meet in the ether.

Elsewhere, Shades of Blue offers new interpretations of Blue Note classics by Madlib's fictional ensembles Yesterday's New Quintet, Morgan Adams Quartet Plus Two, Sound Direction, and the Joe McDuphrey Experience — all of whom are just Madlib playing every instrument.

In recent years, Blue Note has been hurtling forward with a slew of inspired new signings — some veterans, some newcomers. Through that lens, Shades of Blue provides a kaleidoscopic view of the storied jazz repository's past while paving the way for its future.

Kendrick Lamar — To Pimp a Butterfly (2015)

Lamar's game-changing third album featured a mighty cross-section of the most cutting-edge jazz musicians of its day, from Robert Glasper to Kamasi Washington.

While hip-hop has had a direct line to jazz for decades — as evidenced by previous entries on this list — Lamar solidified and codified it for the 21st century in this sequence of teeming, ambitious songs about Black culture, mental health and institutional racism.

"Kendrick reached a certain level with his rap that allowed him to move like a horn player," Overall told Tidal in 2020. And regarding Lamar’s present and future jazz-rap comminglings, Overall adds, "He opened up the floodgates of creative possibilities."

Kassa Overall — Animals (2023)

The pieces of Overall's brilliance have been there from the beginning, but never had he combined them to more thrilling effect than on Animals — where jazz musicians like pianists Kris Davis and Vijay Iyer commingle with rappers like Danny Brown and Lil B.

"I would rather people hear my music and not think it's a jazz-rap collage," Overall once told GRAMMY.com. "What if you don't relate it to anything else? What does it sound like to you?"

When it comes to the gonzo Danny Brown and Wiki collaboration "Clock Ticking," the Theo Croker-assisted "The Lava is Calm," and the inspired meltdown of "Going Up," featuring Lil B, Shabazz Palaces and Francis & the Lights — this music sounds like nothing else.

Over the decades, Black American musicians have swirled together jazz and rap into a cyclone of innovation, heart and brilliance — and there’s seemingly no limit to the iterations it can take on.

Kassa Overall Breaks The Mold And Embraces Absurdity On New Album Animals