Steely Dan’s ‘Complicated’ Relationship With Rap Samples – Rolling Stone

Quantum Criminals, the upcoming book by journalist/critic Alex Pappademas and illustrator Joan LeMay, is a comprehensive Steely Dan biography that doubles as a wild trip through the extended Steely Dan universe — the dazzling, seedy, romantically unromantic world Donald Fagen and Walter Becker created together.

For the most part, the chapters use characters from Steely Dan’s songs as windows into the band’s history, legacy, and lore  — from the jilted outlaw gambler Jack on “Do It Again” to the titular Gaucho in his spangled leather poncho, wreaking havoc in the Custerdome. But there are also chapters devoted to real life figures (“Rikki,” of “Rikki Don’t Lose That Number,” for instance), musicians they played with, and artists they admired (Charlie Parker) or lightly feuded with (the Eagles). There’s even a whole chapter about an inanimate object, “Dan” — the “Steely Dan” dildo from William S. Burroughs’ Naked Lunch that gave the band its name (it turns into a really thoughtful essay on cock rock machismo). 

“Peter/Tariq/Daniel” — excerpted below — is ostensibly about Aja opener “Black Cow,” but delves deep into the group’s complicated relationship with hip-hop and sampling. Peter and Tariq are Peter Gunz and Lord Tariq, who forked over 100 percent of their publishing to Becker and Fagen to sample “Black Cow” on their lone 1997 hit “Deja Vu”; and Daniel is Daniel Dumile, better known as MF Doom, who rapped over an uncleared sample of “Black Cow” on “Gas Drawls.”

Fagen and Becker are notorious for snatching the “Deja Vu” publishing, and could even be impudent about it, as evidenced by a famous scene in their episode of Classic Albums, which Pappademas describes at the start of the chapter. But they’re also “one of the most widely sampled white rock bands of all time,” writes Pappademas, who later places his finger on a higher artistic connection between Steely Dan and hip-hop: “But even if nothing about Steely Dan was hip-hop, everything about them was hip-hop… They also wrote with name-brand specificity about decadent luxury lifestyles and sang in the voices of criminals and sociopaths, withholding moral judgment to get at colder truths about human nature.”

Classic Albums again, another shot of Donald and Walter at the console. Donald cues up the intro to “Black Cow” — a drumbeat under a loping clavinet part played by Joe Sample, founding keyboardist for the Crusaders. He bobs his head a little, then starts rapping: “Uptown, baby / We gets down, baby / Upon the crown, baby.” Walter laughs, doubling over at the control board. Scenes from a marriage: Donald and Walter at the board, exchanging inside jokes. In this case, the joke goes unexplained; either you get it or you don’t.

A few years later, the rapper Peter Gunz sat for an on-camera interview with VladTV, in which the whole story of his life — and his history with “Black Cow” — seemed to come out as one long sigh. In 1997, Gunz and his then-partner, another Bronx MC who went by Lord Tariq, put out their first single, “Deja Vu (Uptown Baby).” The song layered a borough-boosting club chant — “If it wasn’t for the Bronx, this rap shit probably never would be goin’ on”— over a slightly speeded-up loop of the intro to Steely Dan’s “Black Cow.” Released independently, it became a hit, and Tariq and Gunz signed a million-dollar record deal with Sony. But to rerelease “Deja Vu” as a Sony single, Tariq and Gunz were obligated to clear the “Black Cow” sample with Donald and Walter, who as it turned out were willing to authorize their use of it — in exchange for 100 percent of the publishing royalties, sole writing credit, and $115,000 in cash.

“People are under the impression that we put the record out and got sued,” Gunz said. “We didn’t get sued. We got stuck up.” Gunz alleged that around the time “Uptown Baby” broke, Steely Dan had just approved the use of a “Black Cow” sample in a forthcoming song produced by Sean “Puffy” Combs. Combs was riding high in those years with a series of hit singles built around big sloppy bites from ultra-familiar Top 40 hits like the Police’s “Every Breath You Take,” flaunting his ability to pay bank-breaking sample-clearance fees in a way that mirrored the diamonds-and-Bentleys lifestyle-porn subject matter of the music. By beating Puffy to the “Black Cow” sample and mooting whatever plans he had for the song, Gunz said, he and Lord Tariq had inadvertently scotched an undoubtedly lucrative P. Diddy payday for Donald and Walter, and Donald and Walter had seemingly chosen to take it out on Gunz and Tariq in trade. Figuring this was a mere bump at the beginning of a long career, Tariq and Gunz agreed to Donald and Walter’s terms, and 20 years later there was Gunz on VladTV, clearly wishing he had another story to tell aside from the one about how he and his old partner forked over all the rights to what would end up being the only hit song from their one and only album.

Before copyright law caught up with digital-sampling technology and the uses hip-hop found for it, the whole history of recorded sound was a playground and a candy store for any young rap producer with an open ear and access to cheap used vinyl. In 1989, on De La Soul’s “Eye Know,” the Amityville-bred producer Prince Paul set the keys from Steely Dan’s “Peg” against Otis Redding’s whistling from “Sittin’ On the Dock of the Bay” and hooked the chorus around Donald’s voice singing I know I’ll love you better. This was on De La Soul’s debut LP Three Feet High and Rising, an album that marked one pinnacle of hip-hop’s golden age of uncleared sampling and also the beginning of the end of that age. Paul and the group took the creative freedom of their moment further than anyone had before, throwing everything at hand into the album’s porridge: Hall & Oates, Liberace’s version of “Chopsticks,” Bob Dorough’s Schoolhouse Rock standard “Three Is a Magic Number,” Eddie Murphy soundbites, the living-coal-mine voice of Johnny Cash, Fiorello LaGuardia reading Dick Tracy comics over the radio during a newspaper strike — What does it all mean? — and, most infamously, 12 seconds of “You Showed Me,” the Turtles’ 1969 recording of a song by Gene Clark and Jim McGuinn of the Byrds. 

“You Showed Me” was the Turtles’ last top-10 hit. They broke up in 1970. Billed as Flo and Eddie, the group’s founders, Mark Volman and Howard Kaylan, then passed through Frank Zappa’s Mothers of Invention circa 200 Motels and sang backup on a few pre–Can’t Buy a Thrill–era Steely Dan demos, including a very early version of “Everyone’s Gone to the Movies.” In Kaylan’s memoir he says that when Steely Dan first got together, Donald offered him the job of lead singer, a position Kaylan turned down out of loyalty to Volman.

Twenty years after the initial release of “You Showed Me,” De La Soul layered snippets from a French-language instructional record — Il y a saucisse, sans doute — over a four-bar loop of the song’s intro and put it on Three Feet High and Rising as a one-minute interlude called “Transmitting Live From Mars.” Before Three Feet High and Rising was released, De La Soul’s label Tommy Boy Music brokered deals with some of the artists sampled prominently on the record, including Steely Dan, but neglected to reach out to the Turtles. When the album came out and the Turtles complained, the label offered them a flat fee of $1,000, and Kaylan and Volman responded by suing the group and the label for $1.7 million in damages, describing themselves as “genuinely upset with the way De La Soul chopped up and mutilated their song.” 

The case was settled out of court, but two years later rapper Biz Markie was found guilty of criminal copyright infringement over an uncleared sample of the Irish singer-songwriter Gilbert O’Sullivan’s “Alone Again, Naturally.” The case set a precedent, requiring artists to “clear” any reuse of copyrighted music with the owners of the relevant copyrights before releasing it. Since only the most well-heeled artists could afford to pay sample-clearance fees, the decision changed the sound of hip-hop. Sampling didn’t die, but a chilling effect hampered the craft, since anyone who lifted from a recognizable song and failed to clear it risked being taken to the cleaners.

The Turtles (the rest of their legacy aside) would go down in hip-hop history as a scourge on creativity — the greedheads who narced on De La Soul (whose back catalog remained unavailable on streaming services until March 2023, due in part to sample-clearance-related headaches.) 

Steely Dan’s legacy in this department is more complicated. They’re infamous for putting an end to Lord Tariq and Peter Gunz, but they’re also one of the most widely sampled white rock bands of all time. On The Predator, in 1992, Ice Cube and coproducers Rashad and DJ Pooh looped Bernard Purdie’s drums and Donald’s AM-radio-newsbreak keyboards from “Green Earrings” to create “Don’t Trust ’Em,” updating a Steely Dan song about a jewel thief robbing his own paramour — “Sorry, angel, I must take what I see” — into an Ice Cube song warning gentlemen of the Nineties that “the dating game ain’t what it used to be” because today’s independent women are as capable of gaffling as any man. New York rappers Organized Konfusion had already flipped “Green Earrings” one year earlier, braiding it with Verdine White’s bass line from Earth, Wind & Fire’s “Runnin’” to build the backing track for the hectic, pretty “Walk Into the Sun.” 

A few years later, Naughty by Nature and Master P’s “Live or Die” bounced Percy Miller’s signature unnnngh off Donald’s Rhodes piano from “Third World Man,” dialing into the original’s tone of smoked-out, hazy foreboding. In 2004, on the mixtape deep cut “Ride Up,” Freeway and Joe Budden spit screw-faced bluster over a sample of “The Royal Scam”; on his first mixtape, a sixteen-year-old Kendrick Lamar would add his own voice to the track, proclaiming himself the Black Clark Kent, vowing to “chaperone you to a casket,” and rhyming “God’s children, what can you do to us?” with “This rap shit ain’t new to us / Been real since Mama was stroller scootin’ us” like the rap messiah he was about to be. On Sleepy Brown’s “Dress Up,” Brown and fellow Dungeon Family forefathers Ray Murray and Rico Wade fold “Midnite Cruiser” into erotic origami, with Brown’s voice chasing a snippet of the old song’s intro up and down the scale.

And of course there’s Kanye, whose 2007 hit “Champion” digitally fattens a sample from “Kid Charlemagne” into a bloghouse anthem for Day-Glo freaks in shutter shades. “Walter and I listened to [‘Champion’], and although we’d love some of the income, neither of us particularly liked what he had done with [‘Kid Charlemagne’],” Donald said in 2012. “We said ’No,’ at first, and then he wrote us a handwritten letter that was kind of touching, about how the song was about his father, and he said, ‘I love your stuff, and I really want to use it because it’s a very personal thing for me.’ . . . It was such a good letter that we said, ‘All right, go ahead,’ and we made a deal with him.”

The existence, in the world, of “Champion” is proof that Donald and Walter were capable of mercy; they were also capable of mercilessness. “They would not even give us writing credit,” Gunz lamented. “So if you look at . . . the information on the CD, it’s ‘Written by Donald Fagen and Walter Becker.’ Two old, white men. They not from the streets, they not from the hood, they not from Brooklyn, Queens or none of the boroughs. But it was ‘written by’ them.” “So Donald Fagen,” Gunz said with a rueful laugh, “wrote ‘I’m quick to slide off and slide this dick up in your wife.’”

It’s not really that hard to imagine Donald writing a line like that, or at least admiring someone else for having done so. And although his formative years probably didn’t resemble those of 50 Cent or Kool G. Rap, Walter actually was from Queens. That said, if you were an aging rapper who’d been more or less robbed of all right to profit from your only hit song by a couple of guys who looked like seedy trigonometry teachers, you’d probably impugn their street cred, too.

But even if nothing about Steely Dan was hip-hop, everything about them was hip-hop. If the sad tale of Peter Gunz proves anything, it’s that they were about that cash. And they relished taunting their enemies in public — Donald joked about l’affaire Gunz in the Classic Albums doc, but there’s also footage on YouTube of Walter hanging out in his home studio, grinning and showing off a plaque he was awarded for the impressive sales of “his” song “Deja Vu (Uptown Baby.)” They also wrote with name-brand specificity about decadent luxury lifestyles and sang in the voices of criminals and sociopaths, withholding moral judgment to get at colder truths about human nature. In the studio, they sought to combine the metronome thwack of disco records and the irreplaceable sound and feel of live musicians, so their engineer Roger Nichols devised a computer system that would allow them to program drums, snipping the perfect bar and looping it endlessly — years before digital sampling became a commonplace technology and a building block of hip-hop production.

And like so many of the best rappers, Donald and Walter dwelled comfortably in contradiction. For guys who were quick to call their lawyers when sampled nonconsensually, they could be pretty sticky-fingered in their own songwriting. “Rikki Don’t Lose That Number” might not exist without Horace Silver’s “Song for My Father,” after all, and while Silver reportedly took the quotation as a compliment, the same cannot be said for Keith Jarrett, who took successful legal action after Donald and Walter acknowledged how much “Gaucho” owed to his composition “Long as You Know You’re Living Yours.”

A few years before “Uptown Baby” happened, another rapper and producer had also built a song from a piece of “Black Cow,” but didn’t make the mistake of asking for permission. One night in December 1994, while broadcasting live to a narrow band of underground hip-hop fanatics on Columbia University’s student-run WKCR-FM, DJs Stretch Armstrong and Bobbito Garcia stopped busting each other’s balls and futzing with faulty equipment (“Yo, hittin’ it ain’t gonna help”) long enough to press play on a demo no audience had ever heard before. “Coming up right now is my man that’s down with KMD,” Bobbito said. “His name is Doom. Solo joint. Check it out.”

That intro collapsed a whole lifetime into a few words and prefigured years of elusion and half-truth that lay ahead. Daniel Dumile was born in London in 1971 and raised in Long Island, New York; KMD was the rap group he founded in the Eighties with his brother Dingilizwe, known as Subroc. Doom went by Zev Love X. The two KMD albums map a journey from innocence to experience. Mr. Hood is bright and goofy, the sound of young devouts spreading street knowledge like good news; Black Bastards, inspired by former Last Poet Gylan Kain’s proto-rap opus The Blue Guerilla (liner note: “No land, no god, no language, we have nothing of substance other than ourselves. We are the existential reality; philosophers forced to become court jesters to amuse and modify the dickless aristocrats”) sounded crowded, conflicted, and like it was made by people coming down off something. It was still unreleased in April 1993 when Subroc was struck by a car while trying to cross the Long Island Expressway. He died in the hospital that same night; friends remember Dumile playing Black Bastards on a loop at his funeral. Then Elektra Records dropped KMD in a dispute over cover art, and after that people didn’t see Dumile for years.

Later in interviews he’d allude to periods of near homelessness; in his songs he alluded to jail time. Meanwhile he built a myth around his disappearance and reappearance. After he resurfaced, he was never seen in public without a metal mask inspired by the Fantastic Four’s nemesis, Doctor Doom, who in comics canon had been scarred in a laboratory accident while mixing science and black magic. A cult formed almost immediately, superseding KMD’s original fan base, and Doom became one of the most acclaimed rappers of his generation without losing his capacity to bewilder. Like Donald and Walter, he was an artist whose work drew on memories of formative schlock, referencing the Marvel canon, movie monsters like Gheedorah, and pro wrestling; the song “Hey!” lifted horn stabs and haunted-amusement-park atmosphere from the opening credits of Scooby-Doo.

Doom would send masked accomplices out on the road to perform live shows on his behalf, so that each tour generated a new trail of conspiracy theories. He died on Halloween in 2020, of still-undisclosed causes, in England, where he’d been living since being refused reentry to the United States after a tour in 2010 — it turned out he’d never been an American citizen — but news of his death didn’t break until December of that year. One last mysterious lapse of communication, one more mystery to ponder.

When Bobbito Garcia plays the demo version of Doom’s “Gas Drawls” on the radio in 1994, all this is ahead of him. The vocals are double-tracked, as if two Dooms are crowding the mic, packing the margins of the verse with parentheticals and buried asides, rhyming the title phrase with “Breaking glass and plastic jaw like federal drastic law,” the words coming out like trauma-jumbled memories rattling in his armored skull. (Hittin’ it ain’t gonna help.) He gets worked up, but the backing track remains implacable: a loop of the five-second moment in the middle of Victor Feldman’s otherwise busy Rhodes solo where the whole band pauses to let five or six descending notes breathe, plus the voice of Donald Fagen saying, “You were very high,” compressed the way a scratched-in sample always sounds, a record inside a record, a transmission from Mars. Lord Tariq and Peter Gunz sampled the first sound you hear when you drop the needle on Aja, and got caught before they could run; Doom finds a trap door inside “Black Cow,” slips through it, and builds a world inside a crawlspace.

“Excerpted from Quantum Criminals: Ramblers, Wild Gamblers, and Other Sole Survivors from the Songs of Steely Dan, by Alex Pappademas and Joan LeMay. Used with permission from the University of Texas Press, © 2023”