Best Rap Songs that Sample Jazz

What are the best rap songs that sample jazz?

Okay, we know the holy trinity of A Tribe Called Quest, Gang Starr, and Digable Planets laid the groundwork for the best rap songs that sample jazz.

But guess what? The jazz-rap revolution is still in full swing!

This list is your treasure map to the newest gems – where dusty samples meet razor-sharp beats.

Expect the unexpected, and be prepared to update your playlists.

We’ll keep digging, you keep grooving.

Read Our ‘Marvin Gaye’s 18 Most Popular Songs’ Article!

9. Ski Beatz ft. Nesby Phips – “Blue and Green” (2010)

Stream “Blue and Green”: Bandcamp

Jazz Sample: Miles Davis – “Blue in Green” (1959)
Stream: Spotify, Apple Music, Tidal

Buy Miles Davis’ Kind of Blue on Vinyl

Back in 2010, Creative Control announced that superstar producer Ski Beatz had acquired the rights to the Miles Davis catalog and was working on a remix album drawing from the legendary trumpeter’s recordings.

A video clip for the first single, a remix of “Blue in Green” from the 1959 masterpiece Kind of Blue, was released on Youtube, and much to our chagrin that was the last we ever heard of the project.

Rechristened “Blue and Green” and featuring New Orleans rapper Nesby Phips, who was riding high at the time from the rise to fame of Curren$y and the whole Jet Life crew, the track sees the original sped up with extended samples of John Coltrane and Miles’ horns flowing freely over 808s and the backing of The Senseis’ rhythm section.

Altogether cool and suave just like Miles would have wanted it, “Blue and Green” marvelously blends the best aspects of rap and jazz for a song that is the epitome of chill.

Definitely a shame that the record never came to fruition.

8. Westside Gunn ft. Mach-Hommy – “Margiela Split Toes” (2021)

Stream “Margiela Split Toes”: Spotify, Apple Music, Tidal

Jazz Sample: Jackie Trent with The Tony Hatch Orchestra – “The Shadow of Your Smile” (1969)

Westside Gunn has brought a breath of fresh air into rap music since his arrival on the scene in 2005.

A visionary iconoclast and a master in contrast, Gunn revels in melding dichotomies, from intermixing the Buffalo drug-dealing culture with the excesses and luxuries of the 1% to juxtaposing infantile hollers with samples of some of jazz music’s deepest cuts.

His style is an acquired taste the way Basquiat paintings probably were in the late 1970s, yet Gunn’s genius is undeniable and his impact on rap music’s cognoscenti has already been profound.

Case in point, his music inspired Tyler the Creator to “wanna just rap again” and was a catalyst for Tyler’s most recent Grammy-winning album Call Me If You Get Lost.

Although Gunn makes extensive use of jazz samples and a number of tracks could’ve been featured here (including “Ritz Barlton” and its Art Pepper sample) our choice landed on “Margiela Split Toes” from 2021’s Hitler Wears Hermes 8: Sincerely Adolf.

The song’s sample is from an obscure 1969 rendition of the jazz standard “The Shadow of You Smile” by vocalist Jackie Trent and the Tony Hatch Orchestra.

Produced by Camoflauge Monk and featuring Mach-Hommy, “Margiela Split Toes” loops a trumpet riff from “The Shadow of You Smile”‘s opening vamp, and everything else is just as textbook Westside Gunn as can be.

7. Joey Bada$$ ft. Westside Gunn – “Brand New 911” (2022)

Stream “Brand New 911”: Spotify, Apple Music, Tidal

Jazz Sample: Brief Encounter – “Total Satisfaction” (1977)
Stream: Spotify, Apple Music, Tidal

Buy Joey Bada$$’ 2000 on Vinyl

Joey Bada$$ came back from a five-year hiatus in 2022 and dropped a knockout punch and one of the year’s best and most astute rap albums with the long-anticipated 2000.

The record features a slew of samples in addition to various piano melodies (including one by none other than Diddy on the opener “The Baddest”) plus star-studded cameos by Westside Gunn, JID, Chris Brown, and Capella Grey.

Although other songs from the album fit the bill for this list, “Brand New 911”, which sees Bada$$ and Gunn reunited for the first time since 2020’s “327”, stands out with its heavy use of a saxophone loop from Brief Encounter‘s 1977 “Total Satisfaction” (found at the 1:37 mark on the original).

With its trademark Griselda sound effects, stellar verses by two of rap’s biggest names, and an instrumental built around a deep bass line and a hypnotic saxophone riff, “Brand New 911” is just as good as it gets when it comes to rap songs that sample jazz.

6. Trademark Da Skydiver – “Dead Fool” (2010)

Stream “Dead Fool”: Spotify, Apple Music, Tidal

Jazz Sample: Frank Sinatra – “A Day in the Life of a Fool” (1969)
Stream: Spotify, Apple Music, Tidal

Trademark Da Skydiver hails from NOLA and came to prominence as one of Curren$y’s close co-conspirators.

His 2010 mixtape Super Villain Issue #2 is a solid album in its own right and filled to the brim with jazz samples, but rising to the top is the lead single “Dead Fool” sampling the Chairman of the Board Frank Sinatra’s “A Day in the Life of a Fool” from his 1968 classic album My Way.

Although the Sinatra version gives us a particularly gut-wrenching depiction of loneliness, Trademark’s “Dead Fool”, featuring a sped-up sample, shifts the original tone of melancholy into nonchalant confidence.

With its effortless flow, crafty verses, and cinematic Creative Control video clip, “Dead Fool” is a throwback well worth revisiting.

5. Kassa Overall ft. Eric Wyatt, Stas THEE Boss and Nappy Nina – “I’M A KING” (2021)

Stream “I’M A KING”: Bandcamp, Spotify, Apple Music, Tidal

Not quite a sample in the purest sense of the word, “I’m a King” was the lead single off polymath drummer, rapper, and producer Kassa Overall‘s 2021 COVID-era mixtape Shades of Flu 2.

An ode to Madlib’s 2003 Blue Note remix album Shades of Blue, the EP rehashes a wide range of jazz music from classics by Wayne Shorter and Chick Corea to newer repertoire by the likes of Roy Hargrove, ARTEMIS, and Kris Davis.

Of particular interest to us is “I’m a King” which features a disjointed mashup of verses by Overall, Stas THEE Boss and Nappy Nina intertwined with some truly soul-cleansing free-ish trad jazz courtesy of saxophonist Eric Wyatt, bassist Stephan Crump, and keyboardists Sullivan Fortner and Mike King.

Thoroughly satisfying on so many levels, the track is even accompanied by one of the dopest jazz music videos ever released complete with a Van Gelder Studio cameo!

4. Jalen Santoy – “Foreplay” (2016)

Stream “Foreplay”: Spotify, Apple Music, Tidal

Jazz Sample: Stanley Turrentine – “Sunny” (1966)
Stream: Spotify, Apple Music, Tidal

Jalen Santoy first made waves at the tender age of 15 with the release of his debut album God, which caught the eye of rapper Big Pooh.

The two would go on to collaborate and draw attention from several major publications, including XXL and The Source.

Two years later, Santoy would release his Charlie Eastern EP with the lead single “Foreplay” featuring a prominent jazz sample of Stanley Turrentine‘s cover of Bobby Hebb’s “Sunny” off the 1966 Blue Note masterpiece The Spoiler (woah that was a mouthful).

Looping Turrentine’s sultry tenor melody over breakbeats with Santoy’s syncopated flow bobbing and weaving in and out of tempo, “Foreplay”‘s just a killer track that we’ve had stuck on repeat for a minute and a half now.

3. Robert Glasper Experiment ft. Erykah Badu & Phonte – “Afro Blue” [9th Wonder’s Blue Light Basement Remix] (2012)

Stream “Afro Blue” [9th Wonder’s Blue Light Basement Remix]: Spotify, Apple Music, Tidal

Jazz Sample: Robert Glasper Experiment ft. Erykah Badu – “Afro Blue” (2012)
Stream: Spotify, Apple Music, Tidal

Buy Robert Glasper’s 10th Anniversary Deluxe Edition Black Radio 3-Vinyl Set

Originally composed in 1959 by Cal Tjader Sextet percussionist Mongo Santamaria with songwriter Oscar Brown later adding lyrics to the song, “Afro Blue” has since been covered by the likes of John Coltrane, Abbey Lincoln, Dee Dee Bridgewater, and many more.

In 2012, jazz superstar Robert Glasper tackled the composition on his R&B debut album Black Radio accompanied by none other than the legendary Ms. Erykah Badu.

The record received wide critical acclaim in addition to earning Glasper his first Grammy Award win for 2012’s Best R&B Album.

Although the original version is quite outstanding in its own right, Black Radio was also awarded a remix EP, Black Radio Recovered, which features a rehash of the song by producer 9th Wonder and a stellar verse by rapper Phonte.

With lyrics like “Tears of joy in the morning made our pillow wet / Then night fell and we turned into silhouettes / Your body next to mine dancing real close / Step left, step right, then a pirouette” and a solid arrangement by Glasper and Co., this one’s definitely deserving of a spot on this list.

2. Christian Scott aTunde Adjuah ft. Vic Mensa – “Freedom is a Word” (2018)

Stream “Freedom is a Word”: Spotify, Apple Music, Tidal

Bonus Song: Christian Scott aTunde Adjuah ft. A$AP Ferg, Wiki & Your Old Droog – “Complex City Cypher” (2016)

This one’s a bit of a PR stunt yet one of the finest examples of rap and jazz merging forces to create something greater than the sum of its parts.

In 2018, the Tequila brand 1800 commissioned New Orleans jazz trumpeter Christian Scott aTunde Adjuah and rapper Vic Mensa, who was still on the come-up at the time, to get together and create an original piece of music.

The result is the stellar “Freedom is a Word” with its trademark Christian Scott instrumental augmented by the flowing flute lines of Elena Pinderhughes.

Mensa’s verses are perceptive and mature, depicting the struggles of a young and ambitious man fighting to overcome the injustice and inequalities inherent in the “system”, for lack of a better term.

Most interesting is the dynamism, openness, and feeling of freedom that jazz provides as a backing instrumental in contrast to the more common short hooks looped ad infinitum of most rap songs.

This is one for the ages and if you like what you hear also check out the Complex City Cypher Scott recorded two years prior with rappers A$AP Ferg, Wiki, and Your Old Droog.

1. Talib Kweli – “Get By” (2002)

Stream “Get By”: Spotify, Apple Music, Tidal

Jazz Sample: Nina Simone – “Sinnerman” (1965)
Stream: Spotify, Apple Music, Tidal

Straight up one of the greatest singles in rap history, Talib Kweli‘s 2002 debut studio album Quality featured this absolute gem produced by none other than the jeen-yuhs himself Kanye West.

Backed by various samples from Nina Simone‘s 1965 masterpiece “Sinnerman”, from chopped-up piano riffs to impassioned vocals, “Get By” sees Kweli spitting endless bars lamenting the human condition within the inner cities with verses that are just as poetic as they are picturesque in true hommage to the High Priestess of Soul’s long-standing battle for social justice.

You’ve definitely heard this one before, but this is one you can never spin too many times, so just hit play.

Read Our ‘Marvin Gaye’s 18 Most Popular Songs’ Article!

Sebastien Helary

Written by Sebastien Helary

Sebastien Helary is the founder and principal writer for, a premier destination for contemporary jazz enthusiasts. His insightful contributions have also graced the pages of Time Out Montreal and Cult Montreal. Outside the realm of music and food journalism, Sebastien’s personal musings and artistry are showcased at

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