Twenty-five years after its release, hindsight reveals one now-dated aspect of Guru’s Jazzmatazz, Volume 1: The front cover refers to its fusion of hip-hop and jazz as “experimental.” In 1993, the legendary MC was between two classic Gang Starr albums — 1992’s Daily Operation and 1994’s Hard To Earn, both of which were relatively slept-on at the time (3.5 and 4 out of 5 mics from The Source, respectively) but have since become essential entries in late Golden Age East Coast hip-hop.

But while his work with DJ Premier both made and immortalized his rep, Guru had other ideas in his back pocket, too — and the creation of a full-length album featuring a mix of hip-hop production and live instrumentation from a previous generation’s jazz icons must have felt like an odd endeavor. Even with hip-hop’s openness to incorporating elements of jazz, a trend that had taken hold a few years earlier with the soul jazz-sampling work of artists like A Tribe Called Quest and Stetsasonic, the act of foregrounding live players during the peak of sample-based hip-hop might have come across as something of a risk.

Bill Adler’s essay in the liner notes to Jazzmatazz suggest as much. The journalist and historian smartly outlines the lineage of the album’s main thrust, from ’70s Grandmaster Flash DJ sets’ incorporation of Bob James to the Easy Mo Bee-produced 1992 Miles Davis swan song Doo-Bop — not only to give Jazzmatazz a precedent, but to justify its existence in the first place.

The concept felt like it was pushing against an opposition, and Adler found one: “A neo-conservative jazz musician like trombonist Delfeayo Marsalis will sail straight on ahead and beat up on rap for its ‘vulgarity,’ insist that ‘every element in rap is derived from jazz,’ unfavorably compare rap’s greatest practitioners to Shakespeare, Mozart, Louis Armstrong, and Charlie Parker… and rhetorically wonder: ‘What rap has the emotional fortitude to draw any American to tears through its honesty?'” (A quarter-century later, and we still get assorted Marsalises pulling the same rhetorical complaints, so some things are slower to change than others, at least.) Using jazz as a sample component was nothing new to hip-hop, but what would it mean if the two worlds met each other more directly on shared terms?

With that kind of mindset at his back, Guru went into Jazzmatazz, Volume 1 as an artist with something to prove. And after all these years, it feels like one of many Q.E.D.s of the time — a deeper connection to finding the core feelings and vibes of music that had become part of hip-hop’s vocabulary. Hip-hop’s ’70s evolution might have passed largely through the grooves of James Brown and Kool & The Gang records, but the era would prove just as fertile for the radio-friendly soul-jazz crossover work of vibraphonist Roy Ayers, trumpeter Donald Byrd, and keyboardist Lonnie Liston Smith.

All three of those iconic artists appeared on Jazzmatazz at the same time their music was becoming re-popularized through hip-hop samples, while the rest of the personnel came from younger ranks — including singers N’dea Davenport (of the Brand New Heavies) and Carleen Anderson (the daughter of James Brown Revue stars Bobby Byrd and Vicki Anderson), French rapper MC Solaar, guitarist Ronny Jordan, and saxophonists Courtney Pine and Branford Marsalis. (Adler’s liner notes find an amusing irony in the latter musician’s presence.) If anything, Jazzmatazz wasn’t just a referendum on jazz’s place in hip-hop and vice-versa — it was a deliberate effort to maintain a generational bridge between genres, eras, and traditions that acknowledged preservation and growth as partners rather than opposites.

The resulting music was something of a revelation. It made perfect sense in a way that didn’t take a lot of getting used to: hearing a self-overdubbed Byrd juxtapose lively runs over more melancholy solos on “Loungin'” or Lonnie Liston Smith complementing the beat with sharp piano-chord stabs before stretching out on his own solo on “Down The Backstreets” was savvily integrated into the more sample-based production elements, standing out on their own merits without distracting from either the MCing or the beats.

And its headliner was the perfect MC for the job. Guru’s laidback demeanor on the mic, whether he was rapping about street crime, romance, his own mic skills, or just watching the world go by, was half of a unique equation that DJ Premier complemented and completed with a finely tuned ear for jazz-inflected beats. But it was also a mode that Guru was raised in, a familial connection that his godfather put him on a path towards with educational listening sessions heavy on Mingus, Monk, and Miles. By the time he was cutting “Jazz Thing” with Primo and Bradford for Spike Lee’s Mo’ Better Blues in 1990, he’d found his lane as one of the best MCs to sound like an authoritative, expressively observant figure without necessarily projecting any more aggressively than a deadpan coolness.

Though he had his audience of hardcore hip-hop heads in mind when making the record, he found it easiest to write his lyrics with the jazz musician playing live to the rhythm track, the same as he might with a Premier beat providing inspiration. The result was one of the apotheoses of hip-hop as a sort of neo-bohemian continuation of Afrocentric expression, though it was still straightforward and (in Guru’s words) “Jeep-ready” to work as straight-up party music, too.

It turns out that the story of Jazzmatazz is also the story of hip-hop in 1993, or at least a significant crest of its connection to jazz as an ancestral force. The jazz-rap crossover movement had already felt like a growing force in hip-hop at the beginning of the ’90s, and by ’91 A Tribe Called Quest would kick off The Low End Theory with a Q-Tip verse that served as a mission statement for the whole movement: “You could find The Abstract listenin’ to hip-hop/ My pops used to say it reminded him of bebop.” (They then put their money where their mouths were by actually featuring Miles Davis Quintet alum Ron Carter playing double bass on “Verses From The Abstract.”)

And 1992, particularly the second half of the year, was laced by remarkable releases by Pete Rock & C.L. Smooth (Mecca And The Soul Brother), Showbiz & A.G. (Runaway Slave), and the Pharcyde (Bizarre Ride II The Pharcyde) that made classic tracks from the influence of artists like Tom Scott, Eric Dolphy, and Quincy Jones. And Blue Note themselves began putting out compilations under the Blue Break Beats banner in ’92 as well, pointing out a direct lineage from their funkier late ’60s and early ’70s offerings to the crates of the day’s biggest producers. As the first three volume’s LP versions stated on the cover, You Gotta Hear Blue Note To Dig Def Jam!!!

But it all came to a head the following year. ATCQ’s Midnight Marauders, Souls Of Mischief’s 93 ‘Til Infinity, and Freestyle Fellowship’s Innercity Griots all rode on beats that built from likeminded if individually and regionally distinct versions of jazz-rap. Digable Planets hit #15 on the Hot 100, went Gold, and earned a Grammy win with the Art Blakey-sampling “Rebirth Of Slick (Cool Like Dat)” — the video for which was a black-and-white nod to old-school New York jazz-club and Beat culture — while their album Reachin’ (A New Refutation Of Time And Space) built a family tree of jazz-rap from the records Ishmael “Butterfly” Butler’s father gave him.

Even the more hardcore, distinctly no-chill likes of Black Moon (the Beatminerz-produced underground favorite Enta Da Stage) and Lords Of The Underground (the Marley Marl and K-Def co-produced cult classic Here Come The Lords) found those classic Blue Note sounds to be a good place to dig in their heels and bust out some of the rowdiest, grimiest tracks to come out of the East Coast that year. And while it didn’t come out until April ’94, Nas’ Illmatic, aside from being a lyrical masterpiece and perennial candidate for Greatest Hip-Hop Album Of All Time, was steeped in the studios in ’93, with the contributions of Q-Tip, Pete Rock, Large Professor, and DJ Premier forming an all-star team of jazz-hop’s greatest producers, with Nas’ own father Olu Dara playing cornet on the outro of “Life’s A Bitch.”

As far as that live-band “experiment” went, it felt a lot less like some crazy notion within a day: literally 24 hours after Jazzmatazz hit shelves, a Philadelphia-based rap group started independently selling their debut album Organix, the name of which was inspired by their emphasis on playing live instruments — a singular rarity since Stetsasonic had broken up the year before. But the Roots capitalized on that unique place in hip-hop with a Geffen contract and a classic major-label debut in Do You Want More?!!!??! in early ’95, and they haven’t slowed down since. A week after Midnight Marauders dropped, the UK-based jazz-rap fusion group Us3 released Hand On The Torch on Blue Note, combining samples pulled exclusively from the label’s back catalog with live instrumentation by jazz session players; the album subsequently became Blue Note’s first-ever million-selling album.

And by the end of 1994, all kinds of hybrid jazz-hop projects — from Branford Marsalis’ DJ Premier collab Buckshot LeFonque to Herbie Hancock’s breakbeat-heavy album Dis Is Da Drum — picked up where Jazzmatazz left off. Sometimes literally, as in the case of the Red Hot AIDS-benefit series’ Stolen Moments: Red Hot + Cool, which kicked off with the Donald Byrd/Guru/Ronny Jordan collab “Time Is Moving On” and included appearances from nearly every single artist previously mentioned in this article.

It’s easy to ask where it all went after that, even if some of the answers feel kind of obvious. As much as ’93 was a watershed for the fusion of hip-hop and jazz, one album released in the waning weeks of 1992, Dr. Dre’s The Chronic, was exponentially more influential to mainstream hip-hop on the whole, while the more classic New York-style sound was drastically upended by an album that famously dropped the same day as Midnight Marauders — namely Enter The Wu-Tang (36 Chambers), which made the RZA’s pitched-up fragments of melancholy, murky Southern soul an inescapable signature. Easy Mo Bee’s jazz-hop swan song for Miles Davis was critically shrugged at, but he’d find new purpose in the Bad Boy ranks contributing a legendary grip of beats to Notorious B.I.G.’s Ready To Die and throwing in Craig Mack’s “Flava In Ya Ear” for good measure.

Tribe and the Roots eventually went Soulquarian and shifted from jazz to a more malleable and holistic neo-soul sound, Digable Planets cut the beloved but less-successful Blowout Comb before breaking up, Us3 failed to capitalize on their early platinum status, and the coast wars smothered everything in joyless hostility. You could still get that vibe here and there in the late ’90s — whether it was a Ski Beatz production on Jay-Z’s Reasonable Doubt, Hi-Tek on the boards for Black Star, or Chief Xcel’s beats for Blackalicious — but the movement, like most other bright-burning flashes of inspiration, had been subsumed into the bigger whole and drowned out by newer trends.

But the older trends do come back if they’re resilient enough, and the forms they take once the bandwagon got lighter sometimes come around for something just as revolutionary. Blue Note might not have found another Us3 to sell a million for them, but when they handed the keys to the kingdom to Madlib for Shades Of Blue 10 years later, the jazz-reared, idiosyncratic producer was able to blur the lines between live and sampled music so thoroughly — several names in the credits are pseudonyms for himself, sampling his own played instruments — that it was hard to tell whether the songs counted as remixes or covers.

Digable Planets’ Butterfly reemerged as Palaceer Lazaro of Shabazz Palaces, whose experimental-minded hip-hop albums invoke a sort of jazz that might not have actually happened yet, Afrofuturism as speculative fiction. Canadian jazz group BadBadNotGood turned the equation around, turning productions like “Hard in Da Paint,” “Flashing Lights,” and “The World Is Yours”/”Brooklyn Zoo” into mutated standards en route to getting to work with Tyler The Creator, Ghostface Killah, and Denzel Curry. Oh, and Kendrick Lamar’s DAMN. won a Pulitzer with Kamasi Washington and Thundercat on board, so there’s that.

So maybe there’s this feeling, 25 years later, that Jazzmatazz isn’t nearly as outlandish an idea as its creators might have thought at the time. That seems to matter less than the fact it still bumps, though, and slotted between the two Gang Starr classics that bookend it, it captures one of the all-time greatest MCs at a creative peak. Maybe the more important takeaway is this: it’s always worth celebrating when hip-hop finds a way to do the job of preservation that the conservative purists never really could do alone. And the future belongs to those who know where to take the past.