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Disclaimer: The following interview never really happened … unless you believe that cartoon characters can be more real than real people sometimes.

'Oh, you don't know Anderson Ruffin Abbott? Huh." The beady black disks stare at me accusingly through the thick-framed glasses.

The house before us, at King Street West and Dowling Avenue, isn't much to look at: While some heritage features, such as the wrap-around porch, remain, at some point in the original roof was sheared off and a third storey was added, poorly. Add to that the crappy suburban windows, and it's hard to picture anyone important ever lived here.

My tour guide continues, his tone snarkier: "The guy attended the deathbed of Abraham Lincoln and was a Canadian hero! I used to stand at the corner here and just cry at this house until I was asked by tenants to leave."

I stammer. As Globe Real Estate's Architourist, I pride myself on ferreting out interesting historical characters – especially as they relate to architecture – but I'm afraid Wonderdick, er, Mr. Wonderdick (or is it just Mr. Dick?) has the upper hand. Granted, it's a cartoon hand, but my pride doesn't know the difference: Until today, I'd never known about Mr. Abbott, the first Canadian-born black doctor, or that he once owned this Parkdale home.

My walkabout with Wonderdick started off a lot better. Mike Winters, a flesh-and-blood Edmontonian who also happens to be Wonderdick's creator, had introduced us under the tattered archway of the Sunnyside Bathing Pavilion. Under stylized Art Nouveau fish-and-bubbles, we discussed our mutual love of urban flotsam, unscripted walks in heritage neighbourhoods and, eventually, with Wonderdick steering the conversation, street art, city infrastructure and the future of our transit system.

I'd wanted to meet Wonderdick – flâneur, enigma and contributor to "Vicinities magazine" – ever since discovering him online at cartoon-machine.com. While he's not well known in Toronto (which is curious, since he's such a champion of the city), he's a star in Edmonton, where he appears regularly as part of Mike Winters's Cartoon Machine in Vue Weekly, an alternative news and entertainment freebie.

While other characters, such as the bickering couple in Pair Bond and McScoop the News Dog, get laughs, my guess is that residents of that city can't get enough Wonderdick, since, in their minds, he stands for everything that's wrong with Centre-of-the-Universe Toronto.

While it's true Wonderdick wears his left-wing politics on his tweed sleeve, his love of Richard Florida knows no bounds, and even a friendly debate is soon subverted by bafflegab and five-dollar words, I can see through that, since he loves this city as much as I do.

That's why I shrugged it off when we turned to face the 12 lanes of grey asphalt that buried the candy-coloured innocence of the Sunnyside amusement park in 1955 and Wonderdick said, matter-of-factly, "I'm not saying that the construction of the Gardiner Expressway was Toronto's 9/11, but there are some similarities." Or how, seconds later, he was lost in a reverie about being a "dancing bear" in a "traveling Ukrainian circus," and another fantasy about losing his "sepia-toned virginity on the beach" in 1934.

Since it was clear the fresh lake air was making him dizzy, Mr. Winters and I pushed Wonderdick north for the restorative tonic of grit, pollution and grand-but-threadbare Parkdale homes. As we crossed the pedestrian bridge, I asked Mr. Winters about his move to Toronto in 2004. It was to work in the media, he told me, and the freelance cartooning didn't begin until the autumn of 2010. He grew up in suburban sprawl (like Wonderdick), and was shocked at our stock of heritage buildings: "Coming from a western city that is oil-boom based, there is no adaptive reuse, they forget, they just demolished everything.

"Edmonton is sort of like a giant Etobicoke."

Now picking our way through Parkdale, our friend Wonderdick is back to his old self, waxing poetic about the diverse people who make a home here ("CAMH pacers, undergrad bassists, Jamaicans in camouflage pants") and the wonky streets: "It's a chaotic grid structure that suits my sensibilities – somewhat ordered and harmonic, but not overly heteronormative like the rigid, masculine right angles you find in the financial district."

Uh, sure. While whimsical residential details, such as the "sprinkled-on gothic elements, wizard-hat turrets, relentlessly ornate bargeboards that skirt gable roofs, and the odd circular Hobbit-style windows," have Wonderdick frantically and joyously tweeting and Instagramming, the incident at the Abbott house puts him in a darker mood.

To show Mr. Winters and I "the real spirit of Parkdale," Wonderdick stops in front of a home on Melbourne Avenue that has a little birdhouse-like lending library – "I think of the Algonquin word wàdagwaje, which means to 'share one's blanket,'" he says – but his brow furrows and lips pucker as he thumbs through the selections.

"Lots of disappointing pap," he growls. "Maybe next week."

Mr. Winters pulls me aside and suggests, quietly, that we head to the Dufferin underpass, a kind of Wonderdick Fortress of Solitude. In a few Cartoon Machine strips, our favourite flâneur is seen recharging his batteries under the blazing strip lights and tile art, unfazed by the roar of traffic.

It works: "I look around here, with bright lights shining on the cigarette butts, Dorito wrappers and empty poutine slop buckets," Wonderdick says, taking off his glasses to stanch a tear, "and I feel like it's a slide sample of contemporary humanity." When I tell him that, I, too, appreciate this sort of thing, he looks up, unsure if I'm putting him on. He mutters something about the "exanimate" traditional press and waves me off, so Mr. Winters and I leave him there and go for a pint.

After ordering, Mr. Winters slides the very first Cartoon Machine comic book across the table, which features a flying Wonderdick against the majestic Toronto skyline on its cover. It's wonderful for its twisted Archie comic vibe, just as Wonderdick himself – equal parts Captain Canuck and Sesqui the Squirrel (remember Toronto's 150th-birthday mascot?) – is a wonderful addition to the ongoing dialogue about this city.

Mike Winters will be selling the premier issue of Cartoon Machine, which contains 16 Wonderdick strips, at TCAF: Toronto Comic Arts Festival, May 11 and 12, 2013, at the Toronto Reference Library, 789 Yonge St. See torontocomics.com.

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