By his own admission, Homeboy Sandman doesn't slot easily into the greater landscape of hip-hop.

"Got heads turnin' around like 'Who he?'" he raps over the Daisy-Age-via-Minimalism beat of "1, 2, 3," the lead track from his 2014 full-length, Hallways. "Street don't want him around, he too deep/ The deep don't want him around, he too street."

Then again, Homeboy Sandman's not really worried about fitting in.

"That rhyme, the way it's presented, might seem like a negative, but I've thought of it as a positive that I'm able to move throughout these different spheres of existence," he says. "I think different enclaves, different groups, look at me as kind of an outsider given some of my differences."

True enough, the bare facts of Homeboy Sandman's life don't paint him as a typical rap dude. Born Angel Del Villar II to a Dominican heavyweight boxer-turned-lawyer father and a Puerto Rican mother, he was raised in Queens' intensely multicultural Elmhurst neighborhood, and graduated from prep school in New Hampshire before attending the University of Pennsylvania, part of the Ivy League.

He's an astute essayist whose incendiary articles—critical of mainstream hip-hop culture's self-defeating lexicon and dearth of topical diversity—have been published by The Huffington Post and Gawker, among others. Del Villar studied law, and was a semester short of graduating with two different graduate degrees. He taught ninth and 10th grades in New York City's public school system before pursuing rap full time, grinding his way through the city's rank & file by embarking on a shameless self-promotional campaign.

He hit every stage and crowd he could, of course, and also wrote his rhymes in chalk on the sidewalks outside of the offices of music publications, and littered subway trains with stickers and CDs of his music.

"Talent is an empirical thing," Del Villar says. "So, if you find that you have some kind of talent in some kind of field, then it's really all about putting in work. And so all ... the train-bombings that I was doing early on, that's just because I knew I had the goods."

"It's hard out here for a rapper these days," Del Villar spits on Hallways' "Refugee," but his rise has been meteoric since his 2007 debut. By 2009, he was packing New York City's Knitting Factory; in 2010, after dropping his breakthrough The Good Sun, he linked with forward-thinking hip-hop label Stones Throw. His two Stones Throw full-lengths, Hallways and 2012's First of a Living Breed, find Del Villar at a sustained artistic peak. Hometown alt-weekly Village Voice named Hallways the top New York City rap album of 2014, calling it "simply the sound of a master rap writer at work."

Del Villar's appeal comes from his music's melodic charisma, which works in tandem with his mercurial vocal delivery style. At times, he slides into an easy, shy-seeming lilt that suggests the influence of independent New York rap legends Talib Kweli and De La Soul; at others, he revs into a rapid-fire polysyllabic juggle that squares him in the company of Kendrick Lamar's Black Hippy crew.

Like many independent hip-hoppers, Del Villar's an unrepentant moralist who won't rap about guns or avail himself of hollow endorsement opportunities.

"I'm definitely not a brand at all," he says. "Tide is a brand. I'm a person. I change and I grow."

Indeed, Del Villar's staying power as an emcee could be attributed to his music reflecting his evolution as a person. When Del Villar changes his diet—"Used to be vegan/ Now every piece of chicken that I see, I'm eatin'," he spits on "Activity"—he raps about it. When his philosophies change—contrast Living Breed's "Illuminati," a philippic on the darker side of the American dream, with Hallways' celebratory "America, the Beautiful"—he raps about it.

For Del Villar, that personal growth process is inseparable from the artistic process: "Seems like motherfuckers so afraid of life/ so afraid of being wrong, so afraid of being right," he raps on "Activity." "I'm concerned with livin' life greater/ fuck it if I'm wrong, I'll correct the shit later."

"I'm being myself," Del Villar says. "Like many people, I spent much of my early life into conformity and trying to be what I thought I was supposed to be. Not to say that I'm completely over that, but my life is about trying to be myself, trying to be who I am. I feel like the closer I get to being me, the more there's going to be no one like me. For me, I just want to represent that. I don't want to be anything but what I am."