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.

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