1. Lupe Flips “The Legend of Sleepy Hollow”Lupe’s riff on the Washington Irving story about the Headless Horseman ties in perfectly with the irony of the track’s title: “Dumb It Down.”And I’m brainless, which means I’m headless
Like Ichabod Crane is
Or foreplay-less sex is, which makes me sanelessCrane was the schoolteacher pursued by the headless Horseman, not the Horseman himself. Is Lupe “dumbing down” the tale or making fun of Crane, who “loses his head” in fright? (That irony’s part of the original story, too.) Fans of his barrage of wordplay know Lupe’s more likely to fly over our heads than lose his own. Ten bucks says he’s not too sexually frustrated, either.2. Black Thought Blasts the Censored Huck FinnYou best keep a weapon like a shirt tail, tucked in
Because I’m taking n***as out like Huck FinnIn 2011, NewSouth Books announced the release of an edition of Mark Twain’s The Adventures of Huckleberry Finn that replaced all the n-words with “slave.” (Apparently that was supposed to be less demeaning?) Their reason: even though Twain was writing against racists, the slurs made the book too awkward to teach.

In his “NY State of Mind” freestyle, Black Thought references the controversy with maximum political incorrectness, getting off a double entendre, a shot at his rivals, and a dig at white guilt in two quick lines. (As a bonus, he shouts out Ginsberg and Kerouac on the same track.)3. Black Star Rhymes The Bluest EyeThis one might be the deepest homage on the list. Underground pioneers Black Star took a lyrical passage on the black experience from Toni Morrison’s The Bluest Eye…And fantasy it was, for we were not strong, only aggressive; we were not free, merely licensed; we were not compassionate, we were polite; not good, but well behaved. We courted death in order to call ourselves brave, and hid like thieves from life.…and spun it into actual lyrics: the hook for their “Thieves in the Night.”Not strong (Only aggressive)
Not free (We only licensed)
Not compassionate, only polite (Now who the nicest?)
Not good but well behaved
(Chasing after death, so we can call ourselves brave?)
Still living like mental slaves
Hiding like thieves in the night from life
4. Jean Grae Serves It Up to the RighteousThe phoenix from the fire, hell mouth leviathan
I only get killed at the end of time so I’m buying someThis one’s all about context. Named after the unplayable level at the end of vintage video games, the track “Kill Screen” conjures up the afterlife or even the apocalypse. In these lines Jean poses as gamer, prophet, and mythical creature—foretelling her own phoenix-like death and resurrection and name-dropping Leviathan, the biblical sea-beast who’ll be “served up to the righteous at the end of time.”5. André 3000 Compares Himself to Hemingway, Looks ModestAndré 3000’s first verse on Frank Ocean’s “Pink Matter” is a poignant short story in rhyme. But he rhetorically cuts himself off midway through:Hopped into my car; drove far
Far’s too close and I remember
My memory’s no sharp
Butter knife, what a life, anyway
I’m building y’all a clock, stop
What am I, Hemingway?Don’t sell yourself short, Dré! Even Hemingway, who famously loved to shit on fellow writers, would’ve admired that poetic concision. And the dry, understated image of memory being “no sharp butter knife”…Papa approves.
6. All Natural Offers a Whole Courseload of SchoolingThis one’s less famous, but it could almost take up several spots on the list. In two lines from “It’s OK”—So dummies come simple like Langston Hughes
I watch 'em kneel like Zora, and Tom like Cruise—Chicago group All Natural gives a crash course in American lit, alluding to Langston Hughes' satirical alter ego “Simple,” punning on Zora Neale Hurston’s middle name, and throwing in a reference to Uncle Tomming as in Uncle Tom’s Cabin. (Tom Cruise doesn’t count as a literary reference, although he did star in that adaptation of Anne Rice’s Interview With the Vampire.) It all adds up to a devastating triple-edged attack on sellout rappers.7. MF DOOM Channels ShakespeareThey came to ask him for at least some new tracks
But only got confronted by the beast with two backs

–“Sofa King”“The beast with two backs” comes from Shakespeare’s Othello. (Pretty evocative way of describing two people doing it, right? Not bad, Shakespeare.) The villain, Iago, says it to piss off Desdemona’s father—who’s also Othello’s father-in-law:I am one, sir, that comes to tell you your daughter
And the Moor are now making the beast with two backs…In DOOM’s case, he’s mocking -- in the third person! -- the DOOM addicts who come to him for new tracks. He’s got other business to take care of, OK? (Say the track title fast...)
8. The Roots Give It Up For Chinua AchebePlus the Black Thought em-cey, professional-lay
Push pen to paper like Chinua AchebeFrom “100% Dundee” off The Roots' album Things Fall Apart, a title that’s also a shout to Achebe (and W. B. Yeats). Why does Black Thought get a second spot on this list? Because Achebe just died earlier this year, he was a great writer, and he didn’t get enough respect. End of story.9. Method Man Names His Manhood, Victorian-Style(Assume the position)
Stop look and listen
I spit on your grave then I grab my Charles Dickens
-Method Man from “The What,” Notorious B.I.G.“Charles Dickens” = “dick.” You wouldn't think there'd be a whole lot else to interpret here, but Rap Genius says this penis name “underscore[s] the nexus of sex/death/literature,” so it must be true.10. Jay Z Links Twain, Gatsby, HimselfStock markets just crash, now I’m just a bill
History don’t repeat itself, it rhymes, 1929, still
Write like Mark Twain, Jay Gatsby, I park things
Yellow cars, yellow gold…In his contribution to the new Great Gatsby soundtrack, Hov decided to upstage the movie. In a few short bars on his “100$ Bill,” he weaves together a Mark Twain quote, the Gilded Age, the stock market crash of ‘29, Jay Gatsby, and Jay himself. Also, for good measure, Slick Rick and Schoolhouse Rock. Class dismissed.
[P.S. Yeah yeah, the Childish Gambino line. All love to Donald G, but Cummings' sex jokes were better]