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

The Recording Academy has announced 10 recordings to be newly inducted to the distinguished GRAMMY Hall Of Fame as part of its 2024 inductee class and in celebration of its 50th anniversary this year. This year's GRAMMY Hall of Fame additions, the first inductions since 2021, include four albums and six singles that exhibit qualitative or historical significance and are at least 25 years old. The inducted recordings, which will be added to the iconic catalog residing at the GRAMMY Museum, will be honored at GRAMMY Museum's inaugural GRAMMY Hall Of Fame Gala and concert, presented by City National Bank, taking place Tuesday, May 21, at the NOVO Theater in Los Angeles. Tickets for and performers at the Gala will be announced at a later date. 

The 2024 GRAMMY Hall Of Fame inducted recordings range from Lauryn Hill's The Miseducation of Lauryn Hill to Guns N' Roses' Appetite For Destruction. Others include recordings by De La Soul, Buena Vista Social Club, Donna Summer, Charley Pride, Wanda Jackson, Kid Ory's Creole Orchestra, the Doobie Brothers, and William Bell. Eligible recipients will receive an official certificate from the Recording Academy. With these 10 newly inducted titles, the GRAMMY Hall Of Fame currently totals 1,152 inducted recordings.

See below for a full list of the 2024 recordings inducted into the GRAMMY Hall Of Fame, and see the full list of all past GRAMMY Hall Of Fame inducted recordings.

Full list of 2024 GRAMMY Hall Of Fame Inducted Recordings:

3 FEET HIGH AND RISING
De La Soul
Tommy Boy (1989)
(Album)
Inducted: 2024

APPETITE FOR DESTRUCTION
Guns N' Roses
Geffen (1987)
(Album)
Inducted: 2024

BUENA VISTA SOCIAL CLUB
Buena Vista Social Club
World Circuit/Nonesuch (1997)
(Album)
Inducted: 2024

“I FEEL LOVE”
Donna Summer
Casablanca (1977)
(Single)
Inducted: 2024

“KISS AN ANGEL GOOD MORNIN'“
Charley Pride
RCA Victor (1971)
(Single)
Inducted: 2024

“LET'S HAVE A PARTY”
Wanda Jackson
Capitol (1960)
(Single)
Inducted: 2024

THE MISEDUCATION OF LAURYN HILL
Lauryn Hill
Ruffhouse/Columbia (1998)
(Album)
Inducted: 2024

“ORY'S CREOLE TROMBONE”
Kid Ory's Creole Orchestra (As Spike's Seven Pods of Pepper Orchestra)
Nordskog (1922)
(Single)
2024

“WHAT A FOOL BELIEVES”
The Doobie Brothers
Warner Bros. (1978)
(Single)
Inducted: 2024

“YOU DON'T MISS YOUR WATER”
William Bell
Stax (1961)
(Single)
Inducted: 2024

"We're proud to unveil the diverse mix of recordings entering the GRAMMY Hall Of Fame in its 50th year," Recording Academy CEO Harvey Mason jr. said in a statement. "The music showcased here has played a pivotal role in shaping our cultural landscape, and it's a true honor to recognize these albums and recordings, along with the profound influence each has had on music and beyond."

"The artists, songwriters, producers, and engineers who composed this year's inducted recordings are a reflection of the sheer talent and hard work that goes into creating such seminal music," GRAMMY Museum President/CEO Michael Sticka said in a statement. "It's a privilege to be able to welcome these new additions into our distinguished catalog and celebrate the recordings at our inaugural gala on May 21."

The GRAMMY Hall Of Fame was established by the Recording Academy's National Trustees in 1973. The inducted recordings are selected annually by a special member committee of eminent and knowledgeable professionals from all branches of the recording arts with final ratification by the Recording Academy's National Board of Trustees.

This year, the GRAMMY Hall Of Fame Gala will be the first of what will become an annual event and includes a red carpet and VIP reception on the newly opened Ray Charles Terrace at the GRAMMY Museum, followed by a one-of-a-kind concert at the NOVO Theater in downtown Los Angeles. 

The inaugural gala and concert is produced by longtime executive producer of the GRAMMY Awards, Ken Ehrlich, along with Chantel Sausedo and Ron Basile and will feature musical direction by globally renowned producer and keyboardist Greg Phillinganes. For sponsorship opportunities, reach out to halloffame@grammymuseum.org.

Explore the history of the GRAMMY Hall Of Fame

For Baby Keem and Kendrick Lamar, The Melodic Blue was a family affair. The two cousins collaborated on three tracks from Keem's 2021 debut LP, "Range Brothers," "Vent," and "Family Ties." And in 2022, the latter helped the pair celebrate a GRAMMY victory.

In this episode of GRAMMY Rewind, turn the clock back to the night Baby Keem accepted Best Rap Performance for "Family Ties," marking the first GRAMMY win of his career.

"Wow, nothing could prepare me for this moment," Baby Keem said at the start of his speech.

He began listing praise for his "supporting system," including his family and "the women that raised me and shaped me to become the man I am."

Before heading off the stage, he acknowledged his team, who "helped shape everything we have going on behind the scenes," including Lamar. "Thank you everybody. This is a dream."

Baby Keem received four nominations in total at the 2022 GRAMMYs. He was also up for Best New Artist, Best Rap Song, and Album Of The Year as a featured artist on Kanye West's Donda.

Press play on the video above to watch Baby Keem's complete acceptance speech for Best Rap Performance at the 2022 GRAMMYs, and check back to GRAMMY.com for more new episodes of GRAMMY Rewind.

How The 2024 GRAMMYs Saw The Return Of Music Heroes & Birthed New Icons

When people fondly refer back to hip-hop’s golden age, they are talking about hip-hop’s adolescence — an experimental era when no idea was too risky, no innovation too bold, no boundary too established to be broken. This period between the mid 1980s and mid '90s saw hip-hop’s elders transported into new directions as the culture transitioned into the capitalist mainstream.

It is impossible to document this golden era without acknowledging the contributions of the Native Tongues. The New York-based collective — whose core members included now household names such as the Jungle Brothers, A Tribe Called Quest, Queen Latifah, De La Soul and Monie Love — played a pivotal role in reshaping the cultural landscape of both hip-hop and jazz in the mainstream. As a whole, the Native Tongues opted for a more introspective and bohemian approach to their lyricism and melodies.

The Jungle Brothers’ Mike Gee, DJ Sammy B and Baby Bam led the wave with an Afrocentric philosophy. Their 1988 debut album Straight Out the Jungle, set the vanguard of fusing hip-hop with jazz elements. "Black is Black" is perfectly representative of the first tendrils of what would become the canonical Native Tongues sound: an almost whimsical approach to with race relations and social commentary in America, structured with a boom-bap drums and an impressive array of samples (Gil-Scott Heron, Prince, Kool & The Gang). At the opening beats, Q-Tip introduces himself, going "I’m from A Tribe Called Quest" — a harbinger of the yearslong future association as part of the most influential young collectives of the '90s.

Q-Tip and Ali Shaheed Muhammad of Tribe were classmates of the Jungle Brothers in the lower Manhattan high school Murray Bergtraum, and began collaborating as classmates. With additional members Jarobi White and the since departed Phife Dawg, the quartet — and occasional trio — had an impressive five album run: People's Instinctive Travels and the Paths of Rhythm (1989), The Low End Theory (1991), Midnight Marauders (1993), Beats, Rhymes and Life (1996), and The Love Movement (1998). Each release featured a panoply of inspired and progressive approaches to hip-hop, with lyrics and intricate rhyme schemes that ranged from pensive to cheekily adolescent; production drew influence from jazz, bossa nova, rock, and everything in between.

"Check the Rhime" of the classic Low End Theory is exemplary of their dexterity and appeal. Couplets that are deceptively laid back yet remarkably complex — seamlessly veering from discussing capitalism to general braggadocious flair — while the beat integrates everyone from Minnie Ripperton to a Scottish funk & R&B.

De La Soul rounded out the core groups at the heart of Native Tongues. The Long Island-based trio — Kelvin "Posdnuos" Mercer, Vincent "Maseo" Mason Jr, and the late Dave "Trugoy The Dove" Joliceur — played with a colorful and eclectic approach to their jazz tinged sound and visuals (their debut album declared it the age of the DA.I.S.Y. (Da Inner Sound, Y'all) ). De La Soul were unafraid to lean into a sense of whimsy with songs like "Transmitting Live  from Mars," which sampled the Turtles while integrating a looped French lesson. Unfortunately the result would be precarious: the Turtles sued and won for using their sample, setting a dangerous precedent for the industry.

It would not be the end of De La Soul's legal troubles in the industry. Due to negotiations and disputes with Tommy Boy Records, most of De La Soul’s discography was not available on streaming and younger generations. That is, until March 2023, when De La Soul regained the rights to their releases under the label.

Rounding out the Native Tongues are Newark's Queen Latifah and London’s Monie Love (the only non-New Yorkers in the core crew). Each artist is a pioneer  in not just hip-hop’s consciousness space, but leaders for women in the industry. Latifah and Love’s "Ladies First" is an example of their dual function in the collective as chroniclers of both women's and Black issues. The hit record confronted feminist themes and women’s liberation with punch, verve, and dizzying rhyme patterns; the music video addressed trans-continental Black struggles including the plight of South African racial apartheid. The song was an embodiment of the Native Tongues spirit.

There was never an official dissolution to the Native Tongues; rather, fractures, regroupings and  internal conflicts that stopped the collective's momentum in the mid-'90s. Combined with the rise of Bad Boy Records and a new style of hip-hop star.

Yet as the years progressed, there would be multiple extended members that would be affiliated with the Native Tongues movement — Black Sheep, Black Star, Brand Nubian, the Beatnuts, Leaders of the New School, the incomparable J Dilla — showcasing the impact the Native Tongues’ craft and approach had on '90s hip hop. That influence extends to present day, with popular artists such as Tyler, the Creator and Pharrell  crediting the Tongues’ renegade spirit in their own journeys as individuals, rappers, and producers.

The Native Tongues shifted the myopic perspectives of what people believed hip-hop could, would and should be; their influence encouraged hip-hop to expand, shift and impact the mainstream pop world. The collective's legacy remains as a reminder to ignore narrow-minded criticisms of hip-hop culture (and sound) as a single narrative.

6 Highlights From "A GRAMMY Salute To 50 Years Of Hip-Hop": Performances From DJ Jazzy Jeff & The Fresh Prince, Queen Latifah, Common & More

Today, Public Enemy's 1988 album It Takes a Nation of Millions to Hold Us Back is correctly viewed as a watershed not just for hip-hop, but all of music. But when Questlove's father overheard him playing it, it didn't even sound like music to him.

"He happened to pass my room while 'Night of the Living Baseheads' came on and he had a look of disgust and dismay, like he caught me watching porn," the artist born Ahmir Thompson tells GRAMMY.com. "He literally was like, 'Dude, when you were three, I was playing you Charlie Parker records, and I was playing you real singers and real arrangers, and this is what you call music? All those years I wasted on private school and jazz classes. This is what you like?'

"I couldn't explain to him: 'Dad, you don't understand. Your entire boring-ass record collection downstairs is now being redefined in this very album. Everything you've ever played is in this record,'" he says. "If my dad — who was relatively cool and hip, but just getting older — couldn't understand it, then I know there's a world of people out there that are really just like, whatever."

That nagging reality has powered him ever since — whether he's co-leading three-time GRAMMY winners the Roots, authoring books and liner notes, or directing Oscar-winning films.

And that path led straight to Questlove's role as a executive producer for "A GRAMMY Salute To 50 Years Of Hip-Hop," which will air Sunday, Dec. 10, from 8:30 to 10:30 p.m. ET and 8:00 to 10:00 p.m. PT on the CBS Television Network, and stream live and on demand on Paramount+.

Questlove makes no bones about it: working on that 12-minute Hip-Hop 50 revue at the 2023 GRAMMYs was taxing. So taxing, in fact, that he lost two teeth due to the psychological pressure. But he soldiered on, and the result is an inspiring rush of a two-hour special.

"The thing that really motivated me — Look, man, roll up your sleeves and run through this mud — was like, if there ever was going to be a hip-hop time capsule, a lot of the participants in this show are somewhere between the ages of 20 and 60, and everybody's still kind of in their prime," he says.

"So that way,” Questlove continues, “in 2030, 2040, 2050, when our great, great, great, great grandkids are born and they want to look up someone, this'll probably be one of the top five things they look up. And I wanted to be a part of that."

Read on for a rangey interview with Questlove about his role in "A GRAMMY Salute To 50 Years of Hip-Hop," in all its dimensions.

This interview has been edited for clarity.

What can you tell me about your involvement in "A GRAMMY Salute To 50 Years Of Hip-Hop"?

I could be the guy that complains and complains and complains and complains: Man, I wish somebody would dah, dah, dah. Man, somebody needs to dah, dah, dah. And then the universe the whole time is poking you in the stomach like a dog. You think you're going to be drumming for life — like, that's your job.

So I went through this period where I just hated the lay of the land. And now people are like, "Well, the door is open if you want to come and see if you could change it." And for me, it was just important to.

And at first, I was really skeptical about this because even when I was an artist, my peers all the time would — I say in air quotes jokingly, but it's like, man, I know they're serious — they would just call me a suit. Whenever someone's called a suit in a sitcom or it is like, that's always the bad guy. Or especially for me that's known for all this artistry.

But for me, it's like, I can either just sit on the sidelines and watch this thing slowly kind of go in a direction that I don't want it to go. And often with the history of Black music in America, we're innovating this stuff, but we're really not behind the scenes in power positions to control it or to decide what direction it is. And it's a lot of heartbreaking and hard work.

After the success of the thing that we did in March — that 12-minute revue thing — I'll be honest with you. For 12 minutes that was like going through damn near, and I'm not even using hyperbolic statements by saying, coming out within an inch of my life.

When that moment was literally over and I was on the airplane landing back in New York, two of my teeth fell out. That's the level of stress I was [under]. Imagine landing in JFK and I got to rush to "The Tonight Show," but then it's like, Oh, wait, what's happening? Oh God, no! My teeth are falling out! And going to emergency surgery. My whole takeaway was like: Never again.

So of course when they hit me in July, "Hey, remember that 12 minute thing you did? You want to do the two-hour version of it?" I was like, "Hell no." And of course I hell noed for three weeks and it's like, "All right, I'll do it, but I'll just be a name on it. I ain't doing nothing." And then it went from that to like, "All right, what do you need me to do?"

What I will say is it's a two-hour show in which you got to figure out how to tell [the story of] hip-hop's 50-year totality — its origins, its peak period, its first moments of breaking new ground, the moment it went global around the world. You got to figure out a way to tell this story in two-hour interstitials and be all-inclusive. 

It was just as stressful, even up until four hours ago. I'll just basically say that my teeth didn't fall out, thank God. And it was worth everything, because it's really a beautiful moment.

Sorry for that 12-hour answer, but that's just how my life rolls.

It was a great answer. What was your specific role behind the scenes?

Oh, I'm a producer. Jesse Collins called a group of us in to help facilitate: me, LL [Cool J], Fatima Robinson, Dionne Harmon, Brittany Brazil. There's a group of nine of us who were producers.

So, [part of] my actual division of labor thing was finding people to help facilitate music. This is a genre in which maybe the first six years of the art form, there was no such thing as an instrumental. "Or, "Hey, J.Period, can you recreate 'Check Out My Melody' by Eric B. & Rakim with no vocals in it?"

Finding the right people to do the music, sometimes I'd have to do it myself. And a lot of people in hip-hop have been super burnt. Super burnt. And I mean, that's putting it lightly.

And so you're giving these impassioned, Jerry Maguire, help-me-help-you speeches. The amount of times I was like, "Look, I really want you to reconsider your answer. This is our legacy we're talking about."

I'm using terms that a lot of these people, frankly, are hearing for the first time, Because like I've said in past interviews, hip-hop started as outlaw music. No one thought it was going to be a thing. So there's a whole generation that had to lay out the red carpet, just so that the next generation could benefit from it while we disposed of them.

But then that next generation gets disposed of, and then here comes my generation. And then the next thing, you wake up and it's like, "Oh, we're not relevant anymore," and dah, dah, dah.

And I'm trying to convince people, "Wait, you don't understand. Now we have a seat at the table. Now we get to control. All that we talked about, we need to control our destiny, and this is our culture." And there was a lot of that. And some people [were like], "All right, I'll do it for you." [To which I said,] "No, no, don't do it for me. Do it for the culture."

But then there were also people like, "Man, never again. F— all that." And there was also, "Hey, why wasn't I asked?" and all that stuff.  So in these two hours, you're going to see eight to nine segments in which we try to wisely cover every base.

This is the "Lyricist" section, and this is the "Down South" section. And ["Ladies First"] is all about the ladies. And this is for those that passed away. And this is for the club bangers. And this is for music outside of America. And this is for the left-of-center alternative hip-hop.

Yes, we wanted to include everybody, but this is network television. And at that, you only get eight to 12 minutes at a time. So that's even hard. "Hey, why can't I do my chorus and my verse?" "Look, man, you got 32 seconds." If you've ever seen those "Tom and Jerry" cartoons where they're juggling plates in a kitchen — like 30 at a time — I don't recommend that to anybody.

But we got through it. I want everyone to feel proud of where hip-hop has come, because to be nine years old and to get on punishment for hip-hop — you know what I mean? I come from that generation. You've got to pay a price to live this culture.

And now it's established. So that's why I got involved. So there was a lot I had to do. A lot of calls, a lot of begging, a lot of arrangements, a lot of talking to people about clearing their samples, to call up publishing companies: "Look, it's just a four-second segment. It's just one drum roll. Can you please overlook it just for the sake of it?"

The amount of times I had to give those speeches. So yeah, that's what I had to do.

Jesus.

And that's just me. It's nine of us. So there's lighting directions, and choreography, and wardrobe, and dealing with clearance — like FCC, and, "They can't say that." And, "All right, which one of us is going to try to call Snoop to ask him that sort of thing?"

And the amount of Zooms that we were on at five in the morning in the Maldives or halfway around the world.

There must be some component of this process where you recognize that there could never be a perfect two-hour special. There could never be a perfect 200-hour special. There must be something freeing about realizing that nothing can be comprehensive when you're dealing with a cultural ocean like this.

[At one point], I had to take a hip-hop break. And the first thing that I did a week later, after recuperating, was I went on YouTube and I just watched every award show I remember watching — like prime Soul Train Awards back in '87, '88, '89, the years that Michael Jackson was killing the GRAMMYs.

Award shows were so magical to me, when I was a kid. There was a period just between five to maybe 15 or 16 in which I religiously watched that stuff, and you just take it for granted.

When Herbie Hancock did Rockit back in 1983 with all those mechanical break dancers, I wonder the work and the headaches that it took to make that happen. The drummer from Guns N' Roses [was] missing while they had to do "Patience" at the American Music Awards — and Don Henley, of all people, was just on the sidelines like, "Does anyone know how to drum?"

I was in the audience during the whole Chris Brown-Rihanna controversy of [2009]. I was literally at the GRAMMYs. There were like 40 minutes left, and I watched the producer run up the aisles.

Because the thing was, that was the year they decided, "You know what? This is going to be the first year in which we're going to ask artists to double down on stuff. So we're going to have Rihanna sing three songs, and we're going to have Chris do two songs. We're going to have Justin Timberlake. And then, suddenly, their absence now means that there's five major gaps open.

And they had 40 minutes left before they went to go live and I'm watching the producer make an announcement: "Ladies and gentlemen, something just happened. We can't get into it."

The level of viralness now on Instagram or Twitter is expected, but back then it was like, Oh, I wonder what happened? And they're just running up the aisles to Stevie Wonder, "Yo, can you [mimics rapid-fire, inaudible chatter]?"

And I'm looking at him, pondering: What the hell are they asking him? And then Stevie's getting up and doing it, and then, "Jonas Brothers, can you duh, duh, duh? Boyz II Men. Where's Al Green? Is Al Green here?" So literally, I'm watching them solve a headache in real time. And with 20 minutes left, backstage rehearsing, and we were really none the wiser.

I've seen that a few times. My very first GRAMMYs was when Luciano Pavarotti got sick and someone just randomly asked, "Hey, does anyone out there know the lyrics to 'Ave Maria'?" Aretha Franklin raised her hand, and we were all like, 'Wait, we mean the Italian version, like that 'Ave Maria.'" And she's like, "I do know the version."

We underestimated if Aretha Franklin from Detroit, Michigan knew how to sing something in Italian. And within a half hour she was on that stage and she killed that s—.

So it made me literally recapitulate every award show I ever watched.Now I'm watching with the analytical eye: I wonder what headaches it took to put that together? So, it changed me as a spectator and a participant.

I have a friend who's been a dedicated hip-hop fan his entire life. We were talking about the 50th anniversary of hip-hop. He questioned the entire enterprise, arguing that it's an arbitrary number that doesn't mean much to true rap fans. What does the 50th anniversary of hip-hop mean to you, personally?

Well, to me, it's important. There's an interlude that I put on the Things Fall Apart record. The album starts with an argument from [the 1990 film] Mo' Better Blues in which Denzel Washington and Wesley Snipes' jazz musician characters are arguing about just the disposability of the art form.

And it ends with a quote from Harry Allen saying that the thing about hip-hop is that most people think that it's disposable: Let me get what I can out this thing, and I'll throw them out the window. And on top of that, people don't even see it as art. And that really hit me in the gut, because I see the beauty of it.

This is kind of why I got into the game of: first it was with liner notes, and then with social media doing these mammoth history posts. And then it's like, Alright, well, let me write some books, because I'm afraid that no one's doing this level of critical thinking about this particular thing.

I know that the disdain and the dismissiveness that I got from some of hip-hop's participants does sort of stem from a place of ego being bruised. And it's righteous. It's righteous anger. But I also knew that if I sat on the sidelines, then it's like when I have grandkids and they Google this, and if it was a half-assed job, then that's my fault. And I definitely don't want to be the guy that talks, talks, complains, complains, without being a part of it.

So yeah, for the amount of people that prematurely died before the age of 30, and for the startling volume of people that have recently passed away in the last three years because of health issues, cardiac arrest, strokes, a lot of us are dying… You and I are talking right now, right when Norman Lear has passed away at the age of 101.

I just read that in The New York Times.

Dude, can you imagine "Tupac Shakur Dead at 103"? Can you imagine that for hip-hop?

It's a survival tool, because for a lot of us, that was the way out of poverty. It was vital for me. I couldn't just sit back and not watch one person behind the wheel. I have to be the designated driver. So, that's why it's important to celebrate that number.

And a big part of my convincing them was like when they were going to pass, like, "Nah, dog, I'm cool. I got a gig that night," I was like, "Dude, we're not going to do this for the 51st or the 52nd. And frankly, will we be here?" I will be 92 years old if it makes it to the 75th. You know what I mean?

The only person that got in my face was Latifah like, "Excuse me, I will be here for the 75th and I will be for the 100th. You don't know when I'm leaving." So I was like, "More power to you, Dana. All right, good. Queen Latifah will be here for the 100th."

What I'm gathering from what you're saying is that no matter what, it's important to have an organization of this prestige canonize this cultural force.

Oh, absolutely. And I know that oftentimes we play the game of public appearances for the gaze of the establishment. I don't want to get into that thing either: making performative celebrations just so that the mainstream can celebrate us.

I have to say that when you watch it, it really doesn't come off as compromised. This thing really looks good. That was the one thing that we laughed at in the group chat, like, "Man, we just went through Apocalypse Now, and are we all saying it was worth it?"

There are at least three people in my production thread that were sort of like, "Uh-huh, never again. I will never again subject myself." And one of them is dead serious. One of them started doing something the opposite, like, "Nah, I'm just doing classical music from now on. There's no stress there." But it was worth it. It was worth it to me.

*Questlove in 2023. Photo: Jamie McCarthy/Getty Images*

It looks to be a classy, expansive special. I'm excited for it to air.

The best part about it? So if you remember, to me, the star of the 12-minute version that we did at the GRAMMYs in March, was Jay-Z.

It was one of the things where it's like, "Hey, do we even ask Jay-Z?" And that's the one guy we decided ourselves, "Well, let's pass on him because number one, he's already performing with DJ Khaled, so we'll pass on him."

Jay-Z actually wound up being the star of that because he was a fan mouthing it in the audience, which to me was almost like better than us just doing a song with Jay-Z on stage. But the audience is the absolute star.

To see Chuck D smile — I've never seen Chuck D smile. As all these acts are coming out and Chuck D's like, singing [Sly and the Family Stone's] "Everyday People," like Boston fans sing "Sweet Caroline" at Red Sox games. Who knew that Chuck D was so jovial about things? But that's with everyone in the audience watching, supporting each other.

So that to me is also an important thing because as audience members on stage, they're ripping it, but as audience members, they're supporting each other. And that, I think is the most important part, because a lot of my take was like, "Wow, I didn't know that dah, dah, dah was so supportive." Or, "Man, Nelly actually knows every Public Enemy lyric. Who knew?" There are a lot of "Who knew?" moments that will shock people for this show.

I'm so glad you brought that up. That was one of my favorite moments during the Hip-Hop 50 performance at the 2022 GRAMMYs. Jay-Z is a billionaire twice over and a global cultural figure, but we see him in the audience, grinning ear-to-ear like a little boy, doing finger guns in the air.

He's getting his life back. And it's important. Especially now, I'm all about joy. And it's not even just like this particular hip-hop figure celebrating his music.

When Chance the Rapper comes out, again, I'm like, "Wow, [Cee] Knowledge from Digable Planets knows Chance?" And then I was like, "Well, they got kids, so of course I'm sure their kids play around the house." I'm doing all this analytical things like, "Wait, how do they know this song? And this is past their age range."

And that to me is the most telling part of this whole thing, to watch generational people get out of their actual zone and to find out that they're fans of — when GloRilla comes out, to watch [Digable Planets' Ladybug] Mecca mouth the lyrics. I was just like, "Oh, wow, OK."

That kind of puts to bed that stereotype that we only listen to the music in our realm. So, yeah, man — to me, that was the magic part of it all.

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