When I bring up Shad in conversation, I find that the number of people familiar with him is still frustratingly low. Many will shake their heads to indicate they have no idea who I’m talking about, but when someone is familiar with the emcee from London, ON, I can expect a wide grin to emerge onto their face—because they know. They know about the commanding flow, the exceedingly clever rhymes, and the endearing style that make Shad arguably the best Canadian rapper in the game.

Drake is the headline-grabbing icon in Canadian hip-hop, but it was Shad’s TSOL and not Drake’s Thank Me Later that took home the 2011 Juno Award for Rap Recording of the Year. Not long after that upset, Shad was honoured for another momentous achievement: a Master’s degree in Liberal Studies from Simon Fraser University (SFU).

“Basically, we’d do the canon of western literature and then take a range of classes from there,” Shad explains. “I kind of kept it as broad as possible. That was really my intention in going back—learning for its own sake.”

With the complexities of the English language at his disposal, rapping is a way for the self-proclaimed “nerdy jock” to take pleasure in his linguistic gift.

“I think the first thing I gravitated towards with rapping was just the fun aspect of it. It was fun to entertain, fun to make my friends laugh, and just kind of the joy of playing with language,” Shad explains.

Rap is a bona fide form of poetry, but Shad has gotten feedback from fans who are only interested in his music for its poetic elements. On “Stylin,” a single from his Oct. 15 release Flying Colours, Shad takes a bit of a shot at those who say things like “Oh hey Shad, I hate rap but I like you.”

“It’s not a big issue,” says Shad when I reference that line. “I think I address it in a bit of a playful way [….] but it is something that fans might not be aware of: how they’re heard, how they’re understood when they make that kind of remark, which is quite prominent for myself and an artist of my vein [….] I do think it’s worth pointing out.”

For Shad, the canon of rap carries the same weight as the canon of western literature. Take “Fam Jam” for example, a Flying Colours track that borrows the line “Not bad, huh, for some immigrants?” from the Kanye West and Jay-Z collaboration “Otis,” and makes it the chorus hook. He tells me about completing “Fam Jam,” a groovy tribute to the immigrant family and friends he grew up with in London after relocating from Kenya at a young age.

“That was a special one for sure [….] a song like “Fam Jam” is one of those [songs] where I’m trying to be a little more pointed and literally trying to describe a specific experience or situation; in particular a nuanced experience like that one, that really takes time to put into words and to put into music.”

Flying Colours’ “Progress (Part 1: American Pie, Part 2: The Future is Here)” shows off the flip side of Shad’s creative process. He starts off with a vague vision that leads to a seven-minute dystopian critique of ‘American’ identity and culture.

“I think I am talking about America more in the sense of an idea,” he says. “It’s a big song—it’s almost bigger than what I can put into words.”

He explains that the catalyst for the song was a parallel he drew between the premature deaths of Ritchie Valens and Buddy Holly, which are discussed in Don McLean’s “American Pie,” and those of rappers 2Pac and Biggie Smalls.

“And then that got my imagination going and it started spinning off into these cascading images [….] I think really it describes some underlying anxiety around some subconscious feelings about a new age that we’re entering. I think that’s kind of the centre of it.”

Despite occasionally rapping about America, Shad’s current tour takes him almost exclusively through Canada. He’s a fan of the domestic touring experience, especially some of the lesser-known stops.

“There’s little places that people might not know; cities like Guelph or Nelson or Victoria, that are very cool music cities, people are very interested in music and really down for an experience when they come to shows [….] People might not know these kinds of things unless they tour.”

Next week, Shad will be performing in St. Henri, a small district of its own within the greater Montreal city, before heading west and covering the rest of Canada. Not bad, huh, for an immigrant?

Shad performs at the Corona Theatre (2490 Notre-Dame West) at 8 p.m. on Nov. 6. Tickets are $30.65 online.