Danny Brown - "Brown Eyes"

Danny Brown grew up in Detroit's rough Linwood neighborhood and racked up F's all through high school; he went for the free lunches and fucked off the rest of the time.

(Brown scoffs when I tell him he seems like a smart, well-educated cat, judging from his verses.) His friends were making bank by selling drugs, so Brown quit his wack restaurant job and got into the weed- and crack-peddling game. He told Detroit's Metro Times that he once sold crack to a pregnant woman. Through an accumulation of minor legal violations tangentially related to his dealing, Brown got locked up for about a year in the Wayne County jail system.

Years later, Brown is doing the damn near impossible: Uniting fans of street rap and the LA/NYC hipsterati in an awkward group hug of appreciation for his distinctive rapping. Dude titled one of his albums The Hybrid for a good reason. That his haircut more closely resembles Skrillex's than Kanye's also adds to his weird appeal. The missing upper front teeth through which Brown spits his XXX-rated, drug-addled verses add even more oddball allure.

Doing time had a profound effect on the skinny-jeans-wearing MC, who now lives in trendy Royal Oak north of Detroit and digs clothes shopping. For one thing, it forced him to get off drugs. "Being in jail taught me about tactical writing," Brown says over the phone from Houston, where he's on tour with Das Racist. His voice tends to rise to an almost hysterical falsetto when he wants to emphasize a point. "Before, I would just get high and write the first thing that came to my mind. I would write a rap in 5 or 10 minutes and think it was cool. You'd check the music, and after a while it depreciates in value. When I was in jail, I had all the time in the world. Now, it might take me two days to write one 16. All the raps [from jail] were on Detroit State of Mind, which is my favorite. I can't write those raps again. Now I'm high again, but I'm a better rapper than I was then."

Brown currently limits his intake to weed (for existing), Molly (for partying), and Adderall (for working on music). At 30, he says he's "too old to be experimenting with shit."

Brown wrote most of his breakout 2011 mixtape, XXX—recently issued by A-Trak's Fool's Gold label—while on Adderall. The title refers to his age, his dirty lyrics, and his obsession with pharmaceuticals. "It's in my DNA, because my fam liked to get fucked up the same way," Brown reveals on "DNA," which sounds like third-album Soft Machine, of all things.

A blogosphere phenomenon, XXX displays Brown's adroit ability to render his hardcore street-life past, outsize libido, and lust for illicit substances into tales that toggle between hilarity and poignancy. With a delivery that recalls Dizzee Rascal's urgent yelp and E-40's quicksilver cadences, Brown verbalizes over some of the strangest, most gripping productions of the century. XXX's roll call of beatmakers includes Paul White, skywlkr, Frank Dukes, and HouseShoes. "30" sounds like Captain Beefheart crossed with grime king Wiley; "Adderall Admiral" rides a juddering industrial-rock sample of This Heat's "Horizontal Hold"; "Outer Space" and "Scrap or Die" are woozy, space-electro headfucks; the horrorcore of "Blunt After Blunt" could scare the Gravediggaz shitless. On top of all this, Brown drops more allusions to his cunnilingus prowess than a sorority full of LUGs; that gap where his teeth used to be comes in handy, yo. Nobody in rap has more tongue twisters about tongue twisters.

Brown admits that he crafts his words for shock value, but more in the vein of Too $hort than Odd Future. (By the way, he likes both, and is an übernerd about hiphop history, with respect for Def Jux and Cash Money, Nas and Esham.) Brown describes his weird combination of fan bases as "an organic process. I've been in the streets, but once I started going to New York and hanging out at these parties, I found out I was attracted to white girls and I wanted to talk to them. But fashion-wise, they wasn't feeling me, so I had to step my fashion up to get those girls, and eventually that tied into the music."

Brown spews lewd lines because he thinks "people are getting burnt out with the gangsta rap, the shootin'-in-the-head shit. You can't get shock value out of that anymore. I always loved that raunchy, misogynistic early West Coast hiphop, Too $hort or Suga Free. No one was really doing it when I started to fuck with it. I'm just trying to humor kids; I'm not trying to degrade women, although it is degrading. I want [kids'] moms to say, 'You can't listen to that!' Rap music has become something you can listen to with your parents. But not with Danny Brown." He laughs like someone who knows his art's as addictive as the crack he used to sling.