Music Q&A: Hip-Hop Artist and Spoken-Word Poet George Watsky

George Watsky performs a sold-out show at the historic Old Vic Tunnels in London during the 2012 Olympics. (Photo courtesy of Gaby Esensten Photography)

When you glance at 26-year-old George Watsky, your first impression may not be that this is one of the most talented artists making an impressive dent in the hip-hop world today. Why? The innocent, wide-eyed stare? The wiry frame and flannel button-downs? The slight lisp?

Good thing, then, that none of these attributes have affected the cold hard facts. Watsky’s latest album, Cardboard Castles, which was released on March 12, surged up to number one on the iTunes hip-hop charts, beating out Macklemore and Ryan Lewis, who had been sitting comfortably on top for 22 weeks. Watsky is something of an anomaly amongst rappers today: he’s a masterful lyricist whose songs range in emotional depth, often going back and forth between hilarious anecdotes to lightning fast, artful churns of rhymes that reveal raw content about the intricacies of everyday life, particularly as a teenager or a 20-something-year-old. Preparing for a world tour, Watsky took a break from his rehearsal schedule to talk with us before his performance at the Paradise Rock Club on April 1.

How did you first become involved with spoken-word poetry?

I started doing spoken word in San Francisco when I was a freshman in high school. In 2003, I ended up going to see Def Poetry Jam, and a year later I finally got on the show in its final season. That was what allowed me to start touring as a professional artist. I toured college campuses for four years…rapping the whole time while doing spoken word, but I didn’t really catch a break until 2011, when I started getting traction on the Internet.

How did your time in Boston influence your work?

Going to Emerson College helped me move my writing skills into other areas, like theater and screenwriting. Emerson also just helps you have a practical understanding of what it’s like to be an artist and how realistic your expectations need to be if you want to support yourself. You can’t just go out into the world expecting everybody to bow and anoint you the next brilliant artist who’s going to transform the world. You have to be super practical.

Walk me through your journey since graduation.

I moved to L.A. with the intention of trying to make it as an actor. I actually got really far on my first audition! I almost got cast in Project X…and then I didn’t get any callbacks for the next year. I realized I couldn’t just place my fate in the hands of casting directors, so I started churning out my own content. One of my videos went very viral and that changed my trajectory. All of a sudden, people began discovering my other work and coming to my shows.

How does Cardboard Castles differ from your first album?

I think that my musicality has improved since my Watsky album. I don’t consider myself a great singer, but I’ve tried to at least hit my notes better. I think it’s got some of my most accessible material that I’ve ever done on it, and the weirdest. I’m proud of that paradox.

Who are some musicians you’re inspired by? Any dream artists you’d love to work with?

If I could have my absolute wish, I’d have to do something with Andre 3000. I grew up listening to Jurassic 5, and Chali 2na, their lead baritone, is one of my favorite MCs of all time. I’d really want to do a track with him. And I mean, every kid who grew up listening to hip-hop in the early 2000s  grew up idolizing Eminem. I’d love to do a song with Regina Spektor—I think that would be a really cool collaboration.

Do you remember the first big show you played? How was that experience? 

My very first slam poetry final that I did in San Francisco when I was 16 wasn’t the biggest show I’ve ever played, but it was the biggest leap in scale I’d ever made in a short time. I remember it so powerfully—feeling like I mattered, feeling like my voice was important, feeling like there were people out there who wanted to hear what I had to say.

My show at the Gramercy Theatre in Manhattan last July was the best night of my life to date. I did an autograph line afterward and was there for four hours on the curb. The tour is a really important moment for me because I get to play the Fillmore in San Francisco, which is where I saw pretty much every single concert that I went to growing up. That’s really a bucket list important thing for me, to get to play that venue in my hometown.

George Watsky will perform at the Paradise Rock Club on April 1. Below, watch “Strong as an Oak,” the debut single from Cardboard Castles:

And here’s Watsky performing “S for Lisp” at the 2010 Collegiate National Poetry Slam Finals at the Cutler Majestic Theatre: