Homeboy Sandman on the enduring importance of rhyme and his jazz influences

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“Yeah, But I Can Rhyme Though,” the fourth track on Homeboy Sandman’s first commercial release, operates as a manifesto of sorts for the hyper-lyrical Queen-bred rapper.

Finding himself interrogated by a skeptic, the former University of Pennsylvania English major defines himself by what he’s not: a backpacker, a gangbanger, a swagger rapper, a hustler, a slacker, a trapper, a reefer smoker, a pimp or a hipster (even though he’s got a lot of sneakers). In a genre often characterized by artists looking to milk trends for easy marketing, Sandman successfully bucks any attempt at pigeonholing. His defense for his inability to be classified: He can rhyme.

Of course, many rappers can rap well, but few boast the virtuosic ability of the one-time Hofstra Law School student and former saxophone player, who found his calling late, following a few years of teaching in New York City’s public schools. Toying with cadence, complex rhyme schemes and an array of distinct flows, Sandman’s relationship with meter, space and modality alternately recalls a free-jazz-man, his hero Black Thought and the avant-rap stylings of West Coast legends Freestyle Fellowship.

Sandman’s been a hip-hop head since discovering a tape of Fresh Prince & DJ Jazzy Jeff’s “He’s the DJ, I’m the Rapper,” and his style is decidedly “post-underground.” While Talib Kweli had a manifesto that took square aim at bling-era rappers, Sandman’s rhetoric bears little enmity toward the swagger-rappers du jour. He’s averse to ideology; the crux of his mission is merely to get his voice heard. But it’s a powerful voice and one that isn’t afraid of playfulness. Songs about homelessness co-exist with songs about the perils of making mean-mug faces.

Blessed with a relentless DIY work ethic, Sandman’s combination of perseverance and skills has allowed him to earn accolades from the major rap blogs, XXL and the Source, and Hot 97 DJ Peter Rosenberg, who has repeatedly spun him on the New York city urban radio powerhouse. His debut, “The Good Sun,” drops June 1 on High Water Music, and in advance of its release, he spoke with Pop & Hiss about his singular style, his jazz influences and leaving the law for the rap world.

Your song “Yeah, But I Can Rhyme Though” defines you in opposition to what you’re not. Has it been frustrating to be an artist in a genre where most people want to fit into a prevailing trend to get a deal?

I’m a musician, and hip-hop is my genre, but it’s just like jazz players, or country singers or a classical artist. It’s about musicality, talent, rhyme cadence, melody, assonance, alliteration, it’s about the gift I have. Music should have nothing to do with an image; what sets me apart is my ability. Nobody asked John Coltrane what his image was -- it didn’t matter. No one could play the sax like him and nobody raps like me. I make my music to last a lifetime. I love going back to the Roots’ “Illadelph Halflife.” I love music from the 1950s and 1960s. This whole sub-culture in hip-hop of disposable music is not something that I subscribe to. I spend time on my music. There’s no 15/16 in my bars. I spend time on my lines, the production and the craft.

As someone who is obviously about the lyrical craft, what do you think about rappers who have made a point of stressing how their lyrics aren’t really important because they have swag or some other intangible?

People ask me if I’m a lyricist, but how can you be an emcee without being one? This isn’t supposed to be something that everyone can do -- when you take away from the musicality of it all, it becomes an image-based thing, and that’s something I’m so far removed from that you might as well ask me to speak about Dale Earnhardt. I don’t want to do things that have been done before.

You mentioned John Coltrane earlier and you’ve spoken in the past how jazz has influenced your sense of space and notions of musicality. How has it done so?

I used to play the saxophone, and it allowed me to learn that I wanted my flow to sound like another instrument. Even if I’m not saying something…[scats da.da..da..da..daa], that musicality can grab people. And if I can fill that in with magnificent lines and slamming production, I have all the bases covered.

I definitely get this from jazz and from classical music, and from most of the music that I listen to. It used to be that the most famous singers were the best ones, not who’s the prettiest one or who is marketed correctly. I don’t think that people are stupid, I just think that they don’t know any better. I was a high school teacher for two years, and I brought in records for the kids. At first, they were like, ‘What is this garbage?’ but by the end of the week, they were like, ‘What are you bringing in next week?’ I mean, the bestselling album of all time is “Thriller.” Motown sold incredible amounts of records. People want good stuff when they know it’s available.

Your music doesn’t seem to be preaching against the more materialistic major label stuff. You obviously feel passionately about hip-hop, but seem to be arguing less in opposition to things, and more in favor of expanding the number of voices that can be heard. Is that a fair assessment?

I’m opposed to censorship in any form. Everyone should have the ability to have their voice heard. What I want is options. I want a talent-based music community. Take a cat like Jay-Z, he raps about things that I would never rap about from a moral standpoint, but he’s a gifted MC. The difference from now and back in the ‘90s was that N.W.A would say things that I thought you’d never hear people say, then the radio would play them next to Tribe or De La or Wu-Tang. People had a wide range of options. The music targets young people and they don’t know the difference. I’m sure you remember what it was like to be young -- I know I do. I was dumb. Young people are just trying to be cool, and like whatever is presented before them as representing cool.

What made you leave law school for rapping and how did that decision come about?

Before I realized that my true passion was for rapping, I was at Hofstra Law School. Prior to that, I’d been teaching in the New York City Public Schools, but before that I was a bartender, I was in marketing -- one thing that I’m thankful for is that I’ve never wanted to sit around and do nothing. So I decided to go to law school, even though I never thought that I’d be a lawyer.

I did it because I needed to chill from being a weed head. People hate school, but I was always about school. I always tell kids to hit the books for 15 minutes or half an hour before going to the party, and it will change your life. So I went to law school because I figured that all I would have to do was read books and write papers. I’d been teaching kids 14 to 18 and those kids force you to stay on point. If you’re not, they’ll eat you alive. I figured that you can read a book in bed, so I was like, ‘Send me to the vacation spot.’

Download:
MP3: Homeboy Sandman -- ‘Yeah, But I Can Rhyme Though’

-- Jeff Weiss