On Sunday, Feb. 12 news broke that hip-hop lost another legend. David Jolicoeur — who rapped as Trugoy the Dove, Plug Two, Dove, and recently, Dave, as part of the hip-hop trio De La Soul — passed away at age 54. 

Born on Sept. 21, 1968, in Brooklyn and raised on Long Island in Amityville, New York, Jolicoeur was a founding member of the groundbreaking East Coast group. Renowned for dropping frank and satirical statements covering heavy topics on upbeat, dialogue-driven, sample-heavy tracks, De La Soul were innovative outliers on a late '80s and early '90s hip-hop scene flourishing with tough-tongued gangster rap. 

Last month Jolicoeur told Billboard, "I think the element of that time of what was taking place in music, hip-hop, and our culture,I think [De La Soul] welcomed that and opened up minds and spirits to see and try new different things." 

Distinctly true to themselves, an up-tempo, bright and playful form reverberated through their sound and style. This is apparent from their very beginnings in everything from the funky floral album art that covers their debut album Three Feet High and Rising, to the music video for "Me, Myself, and I" where the group is seen side-eyed by fellow classmates in gold chains and dark shades. An accompanying bonus track titled "Ain’t Hip To Be Labeled A Hippie"on the single features a sample from "Hard Times" by Dr. Buzzard's Original Savannah Band and a lyrical breakdown of an acronym for D.A.I.S.Y. which rejects any notions of their assumed status as hippies.

Nominated for six GRAMMY Awards through their career, De La Soul became GRAMMY-winners in 2006 for best pop collaboration with the Gorillaz for "Feel Good Inc."  Their indelible mark on hip-hop was most recently celebrated at the 2023 GRAMMYs where Jolicoeur’s fellow group-mates Vincent Mason a.k.a Maseo and Kelvin Mercer a.k.a Plug One and Posdnuos appeared without him as part of the Recording Academy’s massive tribute to celebrate 50 years of hip-hop. 

De La Soul is part of the soul of hip-hop, pushing storytelling, dialogue and music sampling ahead in the genre (the latter was ultimately responsible for the group’s difficulty reaching mainstream audiences on digital streaming platforms). Recently the group reportedly cleared samples after a protracted two-year battle over sample rights and was gearing up to re-release a body of their work to streaming services on March 3 including 3 Feet High and Rising, De La Soul Is Dead, Buhloone Mindstate, Stakes Is High, Art Official Intelligence: Mosaic Thump, and AOI: Bionix.

Jolicouer will be deeply missed by his fans, the music communities he inspired and his fellow artists, including Pharell who shared his sentiments on Twitter, stating, "Trugoy Dave from De La Soul has gone up to be with the day of the stars with the Master. Sending love, light and positive vibrations to his family, The Soul and everyone whose lives have been touched by his existence. Oodles and Oodles and Oodles of O’s." Rapper and producer Erik Sermon also posted a heartfelt statement in a post on Instagram that starts simply, "This one hurts."

Enjoy a sampling of just a few of De la Soul’s essential tracks, below. 

"Me, Myself and I" (1989)

Released as a single from the group’s debut album 3 Feet High and Rising, the track begins with Jolicouer asking “mirror, mirror on the Tell me, mirror, what is wrong? Can it be my de la clothes? Or is it just my de la song?” It was the group’s only track to make it to number one on Billboard’s U.S. R&B charts. An undeniable bopper, it ranked number 46 on VH1's 100 Greatest Songs of Hip Hop and still instantly gets crowds going today.

The song is also great evidence of their smatter-sampling capabilities, with samples taken from five other artists: "(Not Just) Knee Deep" by Funkadelic (1979); "Rapper Dapper Snapper" by Edwin Birdsong (1980); "Funky Worm" by the Ohio Players (1973); "The Original Human Beatbox" by Doug E. Fresh (1985) and "Gonna Make You Mine" by Loose Ends (1986). 

"Breakadawn" (1993)

A soulful groove that serves as a soundtrack for sweltering summers in New York City, "Breakadawn" was released in 1993 as a single from De la Soul’s third album, Buhloone Mindstate. It samples "Quiet Storm" by Smokey Robinson, the intro to Michael Jackson's "I Can't Help It" from his Off the Wall album. The song also samples "Sang and Dance" by the Bar-Kays.

“Rock Co.Kane Flow ft. MF DOOM” (2004)

From De La Soul’s seventh album, Jake One produces the MF DOOM feature track "Rock Co.Kane Flow" while Posdnuos lays it down: "So systematically inclined to pen lines, without saying the producer’s name all over the track. Yeah I said it! What you need to do is get back to reading credits." The track represented a masterful mashup of minds that ultimately helped Jake One raise his profile. 

In an interview with Passion of the Weiss, Jake One told David Ma, "I don’t even think [De La Soul] knew who I was, but they ended up picking like five different beats and ‘Rock Co.’ was one of them. It was the one that surprised me out of what they picked. And what they do is, [Posdnuos] grabs a bunch of stuff he thinks is dope and Dave listens and has to agree on it. They make sure they’re on the same wavelength but they’re not always on the same wavelength [laughs]." 

"Feel Good Inc." - Gorillaz (2005) 

Released as a single from the Gorillaz second studio album, Demon Days, "Feel Good Inc." featuring De La Soul, secured the group’s GRAMMY-winner status in 2006. 

The song climbed the charts, with the single topping the US Billboard) Modern Rock Tracks chart for eight consecutive weeks and appearing on the Billboard Hot 100 year-end rankings for both 2005 and 2006. The song peaked at No. 14 in the U.S. and within the top 10 in 15 countries, reaching No. 1 in Spain and Greece, No. 2 in the United Kingdom and has been certified five times platinum in Canada and double-platinum in the United Kingdom. 

"The Magic Number" (1989)

Originally released in 1989 on their debut album 3 Feet High and Rising, "The Magic Number" was also featured as the end-credit song in "Spiderman: No Way Home” in 2021 and was re-released in January 2023 to streaming platforms. The Spiderman feature sparked a renewed interest in the group among a new audience of fans, but remained unavailable on streaming platforms due to continuing legal battles over sample rights with the group’s former label, Tommy Boy Records.

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The handful of rap songs released in the 1970s opened doors for the onslaught of creative variation that marked rap albums of the 1980s. Diss tracks, party anthems, socially minded material and gangsta rap all had a place in this era, defined by groups and solo efforts that strove to differentiate themselves from one another. Debuts from the likes of MC Lyte, De La Soul, Slick Rick and others kickstarted not only legendary careers, but a wave of innovations that undeniably led to rap’s commercial takeover in the ‘90s. 

Hip-hop’s four elements (rap, DJjing, breakdancing and graffiti) grew independently and exponentially in form and acknowledgment in the ‘80s. Seldom was it deemed legitimate in the ‘70s but the ‘80s came with it a realization: that big business and big money could be squeezed from the culture. For better or worse, hip-hop began to lodge itself into the mainstream during this decade.  

MTV placements, such as RUN-D.M.C.’s bloated collab with Aerosmith, brought posters into teenagers’ bedrooms and cross promotional ideas to the forefront. Films like as Breakin’ and Beat Street used hip-hop as a dramatic vehicle. And while there was a sense of underlying exploitation, it catapulted hip-hop culture nationally and worldwide. Graffiti was once viewed as vandalism was now on walls and podiums at art galleries, praised as “street art.” Sugar Hill Gang's "Rapper's Delight" seemed light years ago, and there was a palpable sense of maturation and explosion of ideas in the music. 

A colorful cast of new artists pushed boundaries of the time. For one, Marley Marl, of the Juice Crew, was an innovator who preceded Wu-Tang as a super producer who surrounded himself with a motley crew of MCs, each with distinct approaches and personalities. He pioneered methods of drum programming and sampling, all of which began as early as 1983 when he was slowly piecing together the collective. Artists at his helm include Biz Markie, Roxanne Shanté, Kool G Rap, and Big Daddy Kane — all of which were innovators in their own right. 

We’d be remiss not to cite just a handful of the many adventurous artists whose careers began in the '80s:  EPMD, LL Cool J, Ultramagnetic MCs, Ice-T, Jungle Brothers and more. Their work and that of many others ushered in the beginning of hip-hop's golden age, as seen by numerous breakthrough albums in the later part of the decade; 1988 in particular, was a historically fruitful year. 

This late ‘80s era encapsulates the genre's most consequential releases, ones that paved the way for rap to be where it is now. The following  albums took the genre into warp speed, pushing its creative limitations to where it is today.

RUN-D.M.C - Raising Hell (1986)

RUN D.M.C.’s third studio album, produced by Russell Simmons and Rick Rubin, is arguably their greatest — not only in terms of commercial success, but also influence. Their distinct fashion and sound catapulted hip-hop culture (which was still foreign to many at the time) into the commercial realm. 

In addition to juggernaut singles "My Adidas," "It’s Tricky," and "You Be Illin," this album featured "Walk This Way," a wildly ambitious crossover single in collaboration with none other than Aerosmith. It was rap’s first leap into another genre, garnering MTV plays and placing the album all over various music charts. It also was the first rap album to go platinum. Their popularity propelled rap albums that followed later in the decade, and also helped hip-hop gain unprecedented attention in the mainstream.     

Boogie Down Productions - Criminal Minded (1987)

KRS-One’s solo career had many highpoints but his early era with BDP is what cements his legacy. While one of the first albums to have true elements of street edge, its approach vastly differed from that of Schoolly D or NWA. KRS lectured more than rap, he was spiritual and scholarly, weaving more stray observations and warnings of street life rather than glamorizing the violence. 

Scott LA Rock and Ced Gee’s production was also progressive, opening up the sample palette to rock and obscure soul even further. This was not only their first album but also the only one that featured LA Rock, who was murdered about six months after the album’s release. "9mm Goes Bang" and "The Bridge Is Over" are classics that gave the country a peek into the worldview of  New York natives. 

Eric B & Rakim - Paid In Full (1987)

It's hard to think of a greater gamechanger in the art of rap than Rakim, a phenom who rightly went as Kid Wizard on tapes before releasing 1986's "My Melody" with Eric B. At a time when MCs were innocently basic, both structurally and lyrically, Rakim added internal rhymes schemes and multi-syllabic rhymes into his sentences. His voice was a calm monotone. His rhymes were writerly, filled with metaphors and a complexity unseen prior. His many one-liners would be referenced and repeated by generations of rappers including Wu-Tang and Jay-Z. 

Paid In Full was a debut brimming with bonafide classics, "I Ain't No Joke," "Eric B. Is President," and "I Know You Got Soul." On Paid In Full, Rakim moved the needle miles forward for lyricism, altering every rapper that followed.  

Beastie Boys - Licensed To Ill (1987)

Just behind RUN-D.M.C.’s Raising Hell, this rap debut from the brothers Beastie was the second to go platinum in the genre. It was also the only rap album by a Jewish hip-hop group to receive the coveted "5 Mic" rating from The Source, a magazine that was the hip-hop bible of its time. 

The album was unquestionably hip-hop but was also multi-faceted. The track "No Sleep Til Brooklyn" featured a guitar solo from Slayer’s Kerry King, a call-back to the Beasties original rock roots. Songs like "Brass Monkey," "Paul Revere," "Girls," and "Fight For Your Right" were party anthems that kept his-hop’s positive party ethos afloat during a time when the music was shifting towards more serious directions. 

The Beasties were fun, earnest, and distinct — beloved by both purveyors of the culture and fans of it, proving that hip-hop, if done right, is such an inclusionary artform. 

Public Enemy - It Takes A Nation of Millions To Hold Us Back (1988) 

Public Enemy's second album saw the group vastly mature from their debut, Yo! Bumrush The Show. The Bomb Squad's surgical studio techniques raised the bar for production and what was possible in terms of sample layering. 

Chuck D, whose voice is one of the most powerful in all of recorded music, deepened his lyrical content even further, speaking on race, politics, class, power structures, and overall, more socially focused material. Songs like "Black Steel In The Hour Of Chaos," "Don't Believe The Hype" and "Rebel Without A Pause" were a gut punch, a jolt of seriousness and bombast unheard prior and unmatched in its era. It Takes A Nation... charted for 47 straight weeks on the Billboard 200 and many of its profound themes arguably are still relevant today. 

NWA - Straight Outta Compton (1988)

 Eazy-E and company were having a breakthrough moment when this song furthered their ascent into stardom and public infamy. A cacophonous origin story, it gave listeners a worldview most hadn’t heard and a taste of individual talent that was to come. Ice Cube and Dr. Dre soon became huge solo artists thereafter once the group disbanded. As posterboys of the gangsta rap, they had politicians, police, and the FBI all shook. 

By 2015, when N.W.A.’s biopic film cemented their place in popular culture, they had long made history as one of the most consequential groups ever, both musically and culturally. Straight Outta Compton was their unflinching first step that had suburbia clutching its pearls en masse.   

Slick Rick - The Greatest Adventures of Slick Rick (1988)

The ability to tell a succinct story with engaging detail is what makes an MC truly well rounded. Masters of this, Ghostface, Nas, and Black Thought, all have all cited Slick Rick as highly influential. 

This was Rick's solo debut with production from RUN-D.M.C.'s Jam Master Jay as well as the Bomb Squad (of Public Enemy). Greatest Adventures... is forever colorful, anchored by Rick's charisma and ability to spin visual tales. Strikingly imaginative, he raps in different voices and cadences, able to be hilarious and vulgar, making his songs feel like comic strips. "Children's Story" remains a watershed moment of which all future storytelling raps would be measured by.

MC Lyte - Lyte As A Rock (1988)

The involvement of women in hip-hop culture cannot be overstated, despite  being historically marginalized. Case in point:  MC Lyte’s debut was commercially overlooked but its ripples are still felt today. 

With production from Prince Paul, Audio Two and other innovative giants of the time, Lyte’s lyrics addressed drug use, racism, and womanhood. The album’s lead single, "10% Dis," is not only one of the greatest did tracks ever, but was also subsequently sampled and referenced years after, notably by the likes of A Tribe Called Quest, Common, Mobb Deep, and Biggie. Here, at prodigious 18 years old, Lyte solidified herself as not just a formidable female artist, but one the all-time greatest MCs.

Too Short - Life Is Too Short (1989)

In 1989, the West Coast certainly didn’t see the same attention or action as the East Coast, but one Todd Shaw a.k.a. Short Dogg a.k.a. Too Short had been around since 1983, selling homemade cassettes from the trunk of his car in Oakland. Life Is was his fifth album, independently released in 1988 but officially re-released on a major label, Jive, with major distribution a year later.

Short's  presentation was uniquely his own — part street stories, part party music, part pimp fiction. The production eschewed samples for more keyboard and drum machines. It utilized replayed funk riffs and Short’s lyrics were almost cartoonishly misogynistic and obscene. This album in particular exposed him to a national audience, placing  Oakland— and the West Coast — on the map as a new region for rap music. 

 De La Soul - 3 Feet High & Rising (1989)

Prince Paul opened up a new galaxy of innovations on De La Soul's debut. His sampling of kids' records, doo-wop, and left-field sounds coupled with unconventional son structure made 3 Feet High & Rising kaleidoscopic and sunny. 

Paul’s use and insertion of skits became his trademark, adding a movie-like feel to this children’s book of an album. Singles like "Plug Tunin'," "Potholes In My Lawn," and "Me Myself and I" lampooned the gangsta image, making De La's flowery reputation as hip-hop’s hippies even more pronounced. 

Their attempt to shed this persona is why their follow-up was called De La Soul Is Dead. The foundational creativity that informs their brilliant career not only forever altered hip-hop, but it started here. 

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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.

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Among serious music fans, it's a common rite of passage to realize there's a lot more to Steely Dan than meets the eye. And a lot of that is biting, sardonic wit.

If you think Donald Fagen and Walter Becker's three-time GRAMMY-winning partnership is just the stuff of smoothed-over yacht rock, you could have a change of heart: Dan bangers from "Deacon Blues" to "Don't Take Me Alive" to "Hey Nineteen" are full of pitch-black character studies, acidic turns of phrase, and one-liners that may singe your eyebrows.

Sure, this component of the group is key to their conceptual essence. But in your dance with the Dan, take the next step: If you took away all the sarcasm, all the seediness, all the salt, Steely Dan would still be one of the greatest rock bands of all time. Because their musical sophistication was second to none.

For decades, connotations of soft-rock yuppiedom have calcified around Steely Dan; The Onion once summed it up with an article headlined "Donald Fagen Defends Steely Dan To Friends." But not only do they barely resemble yacht rock on any level; their compositions and playing were of a stunning level of sophistication. It's no accident that unquestionable musical godheads Wayne Shorter, Bernard Purdie and the Brecker brothers played with them.

Steely Dan is a tangled web indeed, and a new book illuminates every nook and cranny of their legend. Journalist Alex Pappademas and visual artist Joan LeMay's Quantum Criminals, arrived in May and  pulls apart the Steely Dan myth like Russian nesting dolls.

"We're all looking out at the world with a Donald and Walter-ish kind of dismay. So they make a lot more sense now," Pappademas recently told Rolling Stone. What seemed cold and remote and jerky about them back in the day — now, that's just the way people talk. They're also also writing apocalyptically about their time, and our time now seems so unavoidably apocalyptic.

In the same interview, Pappademas cited the final album of their original run, 1980's Gaucho. "Gaucho is the ultimate one because it's the slickest," he said, mentioning an ultra-complex drum machine they built to remove any vestige of humanity. "Eventually, the solution is, 'We're going to invent sampling so that we can reduce the amount of human error.'"

Of course, Steely Dan didn't literally invent sampling. But the comment at least tacitly bridges two worlds few know are bridged: Steely Dan and hip-hop. As Pappademas put it in the book — albeit in the context of a contentious royalties agreement — “Even if nothing about Steely Dan was hip-hop, everything about them was hip-hop… they were about that cash.”

According to WhoSampled, the Dan have been sampled 152 times; in a number of cases, those samples were in rap songs. Pappademas acknowledges this component of the Dan's legacy in the chapter "Peter/Tariq/Daniel" in Quantum Criminals.

In tandem with Quantum Criminals, let the following list of Dan-sampling rap songs elucidate this misunderstood band for neophytes: they were not only gritty lyrically, but conducive to musical grit.

De La Soul - "Eye Know" (1989)

Smack in the middle of De La Soul's debut album, 1989's 3 Feet High and Rising, is "Eye Know," which samples the Mad Lads' "Make This Young Lady Mine," Otis Redding's "(Sittin' On) the Dock of the Bay," and Lee Dorsey's "Get Out of My Life, Woman."

Underpinning it all is the clavinet from key Steely Dan hit "Peg," a single from their 1977  masterpiece, Aja.

"Hip-hop love this is and don't mind when I quiz your involvements before the sun," Pos raps over the burbling chords. "But clear your court 'cause this is a one-man sport." Between verses, a sampled Fagen bleats, "I know I'll love you better!"

Ice Cube - "Don't Trust 'Em" (1992)

Get past the… er, interesting cover art, and 1976's The Royal Scam is a jewel in Steely Dan's crown — a revisitation of their rock roots as they hurtled into ironic smoothness.

"Green Earrings," about a remorseless jewel thief, is a highlight, and Ice Cube incorporated a sped-up sample of its keyboard part in "Don't Trust 'Em," from his 1992 album The Predator. 

The crystalline-toned hook is woven into brutal storytelling, as the former N.W.A. MC details how a sexual encounter can get you hogtied in a trunk: "You can't trust a big butt and a smile," Cube sagely warns.

Lord Tariq & Peter Gunz - "Deja Vu (Uptown Baby)" (1997)

Aja's opener, "Black Cow," remains of one Steely Dan's all-time funkiest cuts, and it provides the engine for East Coast rap duo Lord Tariq and Peter Gunz's debut single, "Deja Vu (Uptown Baby)".

As Pappademas lays out in Quantum Criminals, Fagen and Becker would only clear the sample if they received 100 percent of the royalties. "People are under the impression that we put the record out and got sued," Gunz said, according to the book. "We didn't get sued. We got stuck up." "Deja Vu (Uptown Baby)" turned out to be Tarique and Gunz's one and only hit song, from their one and only album.

MF DOOM - "Gas Drawls" (1999)

Other MCs clearly got the memo on "Black Cow": it shows up early on the late MF DOOM's "Gas Drawls," from his 1999 debut album Operation: Doomsday, and pops up repeatedly throughout the song.

"You were very high!" Fagen crows just before Dumile punches in, in media res: "By the way, I re-up on bad dreams, bag up screams in 50s/ Be up on mad schemes that heat shop like jiffy."

Kanye West - "Champion" (2007)

Like Ye's cartoon-bear mascot on the cover of 2007's Graduation, "Champion," a cut from that album, blasts into the air — buoyed by a vocal sample from Steely Dan's "Kid Charlemagne."

"Did you realize/ That you were a champion in their eyes?" Fagen croons as the song's chorus, giving "Champion" its thrust as well as its title. At first, Fagen and Becker were reluctant to clear the sample; they relented after West sent Fagen a heartfelt, handwritten letter.

Today, the verse resonates in the rapper now called Ye's legacy — not only for this particular song, but because it seems to sum up his rise and fall. Clearly, Pappademas was right: Steely Dan has nothing to do with hip-hop. Steely Dan is hip-hop.

9 Revolutionary Rap Albums To Know: From Kendrick Lamar, Black Star, EarthGang & More

Music's Biggest Night, the 54th Annual GRAMMY Awards, will air live from Staples Center in Los Angeles on Sunday, Feb. 12 at 8 p.m. ET/PT on CBS.

 In the weeks leading up to the telecast, we will take a stroll down music memory lane with GRAMMY Rewind, highlighting the "big four" categories — Album Of The Year, Record Of The Year, Song Of The Year, and Best New Artist — from past awards shows. In the process, we'll examine the winners and the nominees who just missed taking home a GRAMMY, while also shining a light on the artists' careers and the eras in which the recordings were born.

 Join us as we take an abbreviated journey through the trajectory of pop music from the 1st Annual GRAMMY Awards in 1959 to last year's 53rd Annual GRAMMY Awards.

48th Annual GRAMMY Awards
Feb. 8, 2006

Album Of The Year
Winner: U2, How To Dismantle An Atomic Bomb
Mariah Carey, The Emancipation Of Mimi
Paul McCartney, Chaos And Creation In The Backyard
Gwen Stefani, Love. Angel. Music. Baby.
Kanye West, Late Registration

After trumping Michael Jackson's Bad for the Album Of The Year trophy in 1987, U2 cleared yet another hurdle by beating out one-fourth of the Beatles, 2012 MusiCares Person of the Year honoree Sir Paul McCartney [http://www.grammy.com/news/paul-mccartney-to-perform-at-2012-musicares-person-of-the-year-gala\]. How To Dismantle An Atomic Bomb, said to be the group's return to the big-anthem classics produced in the '80s, charted at No. 1 on the Billboard 200 and garnered seven additional GRAMMYs in 2004 and 2005, including Best Rock Song for "City Of Blinding Lights" and "Vertigo." Also making a comeback of sorts was Carey, whose 10th studio release, The Emancipation Of Mimi, won her three GRAMMY Awards, including Best R&B Song for the No. 1 hit "We Belong Together." In 1990 Carey won her first two GRAMMYs, including Best New Artist. For Chaos And Creation In The Backyard, produced by GRAMMY winner Nigel Godrich, McCartney returned to the one-man band style exhibited on his self-titled solo debut, playing nearly every instrument on the album from guitars and keyboards to bass and drums. Stefani earned a nomination for her solo debut effort, Love. Angel. Music. Baby. The album spawned four additional nods and featured her first No. 1 single as a solo artist, the infectious "Hollaback Girl." West's sophomore release, Late Registration, marked his second Album Of The Year nod (he also received recognition for production work on Carey's The Emancipation …). The album topped the Billboard 200 in 2005 and featured the No. 1 hit "Gold Digger."

node: video: U2 Win Album Of The Year

Record Of The Year
Winner: Green Day, "Boulevard Of Broken Dreams"
Mariah Carey, "We Belong Together"
Gorillaz Featuring De La Soul, "Feel Good Inc."
Gwen Stefani, "Hollaback Girl"
Kanye West, "Gold Digger"

Rock reigned supreme in the Record Of The Year category as Green Day won for their hit "Boulevard Of Broken Dreams." The track appears on American Idiot, which won the group a GRAMMY for Best Rock Album the year prior and gained them presence on Broadway when it was later made into a musical in 2009. Carey's "We Belong Together" skyrocketed to the top of several pop charts in 2005 and earned her two GRAMMY wins, including Best Female R&B Vocal Performance. Adding variety to the field was virtual hip-hop group Gorillaz with the viral "Feel Good Inc." featuring De La Soul. The track earned them a GRAMMY for Best Pop Collaboration With Vocals and a virtual duet with Madonna on the GRAMMY telecast. Stefani's "Hollaback Girl" scored a nomination with the help of GRAMMY-winning producers the Neptunes. West's "Gold Digger," which features Jamie Foxx sampling pieces from Ray Charles' "I Got A Woman," garnered the 14-time GRAMMY winner a win for Best Rap Solo Performance.

node: video: Green Day Win Record Of The Year

Song Of The Year
Winner: U2, "Sometimes You Can't Make It On Your Own"
Mariah Carey, "We Belong Together"
John Legend, "Ordinary People"
Rascal Flatts, "Bless The Broken Road"
Bruce Springsteen, "Devils & Dust"

The second Song Of The Year win for U2, the emotional "Sometimes You Can't Make It On Your Own," was written by Bono and U2, and also garnered the self-proclaimed best band in the world a GRAMMY for Best Rock Performance By A Duo Or Group With Vocal that year, beating out Coldplay, Foo Fighters, Franz Ferdinand, and the Killers. Carey's third nomination in the General Field was co-written with an all-star cast that included Johnta Austin, Babyface and Jermaine Dupri. Making his GRAMMY debut this year was Legend, who co-wrote "Ordinary People" with Black Eyed Pea will.i.am. The singer/pianist's debut studio album, Get Lifted, won a GRAMMY for Best R&B Vocal Album, a trophy that was replaced [link to: http://www.grammy.com/news/legend-gets-a-do-over\] in 2010 by The Recording Academy after an incident involving Legend's nephew. One of the first country groups in recent memory to receive a Song Of The Year nomination was Rascal Flatts' "Bless The Broken Road," written by Bobby Boyd, Jeff Hanna and Marcus Hummon. The track, previously recorded by the Nitty Gritty Dirt Band, won for Best Country Song. The final entry, Springsteen's self-penned "Devils & Dust," which appears on the No. 1 album of the same name, earned the Boss five GRAMMY nominations this year, including a win for Best Solo Rock Vocal Performance.

node: video: "Sometimes You Can't Make It On Your Own" Wins Song Of The Year

Best New Artist
Winner: John Legend
Ciara
Fall Out Boy
Keane
Sugarland

Neo-soul artist Legend, who made two big debuts in 2005 with his first studio album and first appearance at the GRAMMY Awards, picked up Best New Artist honors. Get Lifted also broke the Top 5 on the Billboard 200. Texas-native Ciara, named the "First Lady of Crunk and B" by producer Lil Jon, scored a nod. She also took home a Best Short Form Music Video GRAMMY for "Lose Control." Pop/punk outfit Fall Out Boy received their only GRAMMY nomination to date. The group's 2005 album, From Under The Cork Tree, peaked at No. 9 on the Billboard 200. Piano-driven pop/rock group Keane added more variety to the diverse field, and picked up a second nomination the following year for "Is It Any Wonder?" The second country act to garner a nod in the General Field was the then-trio Sugarland, featuring Kristian Bush, Kristen Hall and Jennifer Nettles. The group won a GRAMMY two years later for Best Country Performance By A Duo Or Group With Vocal — minus Hall —for the tear-jerker "Stay."

node: video: Carrie Underwood Wins Best New Artist

Come back to GRAMMY.com tomorrow as we revisit the 49th Annual GRAMMY Awards.

Follow GRAMMY.com for our inside look at GRAMMY news, blogs, photos, videos, and of course nominees. Stay up to the minute with GRAMMY Live. Check out the GRAMMY legacy with GRAMMY Rewind. Keep track of this year's GRAMMY Week events, and explore this year's GRAMMY Fields. Or check out the collaborations at Re:Generation, presented by Hyundai Veloster. And join the conversation at Facebook, Twitter, and YouTube.