Besque has been spending parts of his summer in the stark opposite of blingy, marquee-name environments: namely, nonprofit organizations serving the poor and homeless in New York, Washington and Toronto's own Moss Park. The aim is to create a video and brief documentary for "Not Enough Love," one of Besque's fall singles.

"[Not Enough Love] is basically looking at poverty and how people have become so desensitized to the homeless," he explains. He hopes the video and doc will show some of what's most impressed him in these places -- "the bond between the [shelter] volunteers and the folks that they're serving. They have strong relationships, even genuine friendships, which I've found pretty incredible." 

Besque's music has long been a fusion of politics, play and personal struggle. His 2002 song "Choked Up"  deals with the sudden, traumatic loss of his girlfriend in a car accident. In 2008, Besque's "Marlboro Man" took on the Bush regime while his "Politics Of The Blaow" addressed Palestinian suicide bombers. "Understand," released last year, compiles some of the stories his friends had to tell about the difficulties of immigrating to Canada. And on the lighter side, "Three's Company" (which also came out in 2010) is an ode to 1980s television from The Facts of Life to Falcon Crest. 

Overall, Besque looks for what he calls a hip-hop "balance" between amusement and analysis. "When we were young, we had party records, which was great, but at the same time you had acts like Public Enemy that would really test you in terms of questioning your surroundings, institutions, school and government." 

The son of landed-immigrant parents from Jordan and Palestine, Besque (aka Steven Kawalit) was born in 1981 in Malton and grew up in Mississauga. Inspired by groups like Public Enemy and a Tribe Called Quest, he started making music when he was a 16-year-old at St. Francis Xavier Secondary School, forming the duo Babylon Point with his cousin. A big break came in 2000, when their demo was reviewed in Vice.

"That really opened my eyes," Besque says, "that you could be from Canada and all of a sudden be picked up on shelves across North America. That's when I really got hungry and decided to take it serious."

As a solo artist, Besque released his first commercial-radio single in 2002 and then signed to UK label Sin Hombre. In 2005, his debut full-length The Frenzy of Renown was released, and in 2007 it was nominated for Juno's Rap Recording of the Year. By 2008, Besque had toured widely and released two more albums, Hang Your Heroes on Urbnet and Last Life in the Universe on Japan's Yanase. He'd also made a big decision -- to go independent and split from the label system, where he felt there was too much pressure to make every song a commercial success, and too many consequent creative constraints.

"Now that I'm free, I can do whatever I want, and that's a beautiful feeling," Besque says, noting projects like "Not Enough Love" likely wouldn't have emerged in a label context. The same might be said of his wide-ranging Nuclear Ambitions album, released independently in July 2010.

But while Besque may have left the big labels, he still has to deal with the changes that've been challenging everybody in the music industry. "To monetize in a digital space is not easy," Besque admits. "MP3s have really ruined the album [format]."

As a result, Besque has decided to do an online "onslaught of singles" this fall accompanied by visual motifs from Toronto animator Andre Guindi. He's also continuing to draw on his day-job expertise as a marketing manager: "There's so much noise out there, so in terms of sticking out using marketing, retention tools and using social media, I've been lucky." 

Bricks and mortar also still matter, of course, and Besque contends that the GTA has tons of on-the-ground advantages there. "Different venues in the city -- from dives off Spadina to bigger clubs like Sound Academy -- are really good about showcasing hip-hop acts," he says, with the same going for festivals. "To get into SXSW is a super struggle but NXNE, they're willing to hear all types. You don't have to have a multinational backing you; if you're good, they'll put you on." The fact that Toronto acts like K'Naan, Drake and the Weeknd have won international fame has also changed the profile of hip-hop nationally for the better, he says.

Change -- this time personal -- is also on the horizon for Besque as he anticipates a move downtown to Liberty Village this fall. "I'm such a yuppie!" he jokes of his neighbourhood choice. "My friends, when they're purchasing, they're going to Milton and further west. But I'm like, no I'd rather live in a coffin… for unbelievable amounts of money! Ha!"

What's likely to stay constant, wherever Besque is, are the personal rewards that come with making music.

"Music washes the soul of the dust of day-to-day life," he says. "It definitely is my therapy." 

Leah Sandals is a freelance writer and editor who lives in the Leslieville neighbourhood of Toronto.