Bob’s Three Cartoon Looks — The Many Faces of a Toronto Street Photographer

This week, something unexpected happened—something that might define the “Bob brand” for years to come.

This week, Bob got three cartoon versions of himself.

And each one captures a different side of my street-photography life in Toronto.

Let’s break them down.

Cartoon Bob #1 — The Documentary Photographer on the Streets

(Downtown cartoon holding the camera)

This one shows me right in the middle of downtown Toronto—surrounded by buildings, traffic, and people moving in every direction. The camera is up, the Blue Jays hat is down, and the expression says:

“Something interesting is about to happen… and I’m ready.”

This is the serious Bob.

The documentary Bob.

The guy who walks the city not just to take pictures, but to tell stories.

And here’s the funny thing: even in cartoon form, I look just enough like a tourist that people still approach me:

“Are you visiting Toronto?”

“Do you need help getting around?”

It makes me laugh every time—but it also helps me immensely.

Because looking like a tourist makes Bob approachable.

People relax around me.

They smile.

They talk.

And that’s exactly how I capture real, human Toronto moments.

Cartoon Bob #2 — The Relaxed Bench-Sitting Explorer

(Cartoon face on Bob’s real body sitting on a bench)

This version shows the calmer Bob—the observer.

Camera resting in my hands, sitting comfortably on a bench, waiting for life to drift right into the frame.

This is the Bob who finds a good corner, sits for twenty minutes, and watches the world unfold like a stage show.

And once again, this is when people are most convinced I’m a tourist.

“How long are you visiting?”

“Is this your first time in Toronto?”

I always smile and say, “I live just down the street.”

But the truth is?

This “tourist energy” actually helps me gather the stories I put into my blogs.

People feel safe approaching someone who looks like they’re just admiring the city.

And that’s when the best conversations — and the best photos — happen.

Cartoon Bob #3 — The Bucket-Hat Field Photographer

(Close-up bucket hat cartoon portrait)

This third cartoon might be the most “Bob” of all.

The bucket hat tied under my chin.

The practical jacket.

The focused but friendly expression.

This is the field photographer version of me—the Bob who blends into parks, trails, waterfronts, and festivals without being noticed. The guy who walks for hours in all kinds of weather just to find one moment worth capturing.

And yes… this version also screams “tourist.”

But again—it works in my favour.

People walk past me without a second thought.

They act natural.

They do what they normally do.

And that’s when the real Toronto shows itself.

But the biggest surprise?

All three versions look just enough like a tourist that people feel comfortable around me.

And that’s one of my storytelling tools.

Tourists are allowed to stop.

They’re allowed to look up.

They’re allowed to take photos of anything and everything.

And that freedom—combined with my love of photography—lets me tell the Bob stories people enjoy reading.

If you see one of them out there on a sticker, badge, poster, blog header, or who knows where else…

just know the real Bob is nearby—camera ready, tourist look activated, waiting for the next great moment in this amazing city.

Toronto isn’t going to photograph itself.

Time to get back out there.