If you’ve scrolled by a photo of Drake on Instagram or watched one of his recent music videos, including February’s “When To Say When & Chicago Freestyle,” then you’ve likely seen Theo Skudra’s work. The Toronto native has been documenting the rapper – and the world that has developed around him – for the past eight years, often in his signature black and white style. But he’s not just Drake’s photographer: Skudra is a visual artist, filmmaker, writer and producer who also happens to take album‑art‑worthy snaps of the rapper backstage, mid‑performance and alongside everyone from Adele to Jay‑Z. We caught up with Skudra to talk about the nostalgia of film, the realities of tour life and how he gets the perfect shots of Champagne Papi.
Documenting life on the road.
enRoute How did you get into photography?
Theo Skudra My dad was a photographer, so when I was growing up there were cameras everywhere and his photos were on the walls. And my mom was an avid art and photography fan. I started to take it seriously on family vacations. I’d be the 10‑year‑old with a camera taking snaps of everybody. I’d show my dad, and he’d tell me what he liked – what worked and what didn’t.
ER What’s your shooting style?
TS Vivid photojournalism. I don’t do cover photos. I don’t do studio shoots. A lot of what I do is fieldwork, whether that’s life on tour or a night in the studio.
ER How do you know when you have the perfect shot?
TS I try to capture heightened moments. Maybe Drake’s on stage and there’s a leap or a blast, or a fan loses their mind at just the right second. I find myself clicking whenever it feels like the top spike in the beat – and gravitating toward those shots in the edit. And then the opposite end of that is looking for somebody who’s in their own private moment, especially when you’re in a busy environment. Those down moments are interesting, maybe because they’re rare or because the person is less aware of the camera.
ER What do you love about shooting on film?
TS Part of it might be my history with it and the nostalgia of how film operates. But I also love the look of it. For the last year, I’ve been shooting on 16 mm, and there’s something about the esthetic. Film reacts to light in a way I connect with – when I see the way those blown‑out highlights look in Casino, or the sky during magic hour in Days of Heaven, or how vivid Larry Towell’s black‑and‑white photojournalism is, I think, “That’s what I want.” It’s almost like every shot becomes instantly classic and nostalgic.
“I try to capture heightened moments. Maybe Drake’s on stage and there’s a leap or a blast, or a fan loses their mind at just the right second.”
ER When did you meet Drake?
TS I was working on films with some mutual friends who were actors on Degrassi. One day, they asked me if I wanted to come to a rehearsal that Drake was having. This was before Take Care came out. I was a huge fan, so walking into that rehearsal space was surreal. I didn’t really start working with him until the set of “Marvins Room.”
ER And how did that come about?
TS I was a digital‑image technician for that video, so I would receive all the memory cards and dump them onto hard drives. But I also brought my camera to set. The first photo I took of Drake, I snuck while he was in a dark corner. The director kind of snapped at me and said, “You can’t be taking this photo.” Then Drake appeared and was like, “What are you talking about? It’s all good. Let him do what he wants.” And then he turned to me and said, “Just send that to me after.” He used that first photo as the single art for “Trust Issues.” After that, I kept getting asked to come out for music videos, or events, or whatever he was doing. I was on the set of “Headlines” when Drake asked me if I wanted to come on tour. That was about eight years ago.
ER What does a typical day of shooting look like?
TS The majority of what I do is split between photography and filming. We have a really organic process between the two of us. Drake is comfortable with me being around with a camera, so I’m constantly filming. Then that can get turned into anything: promotional outreach, a trailer for an album, footage for a company that is working with him.
ER What’s the touring experience like for you?
TS I always have a camera with me, which means that even if I’m having dinner with everybody, I’ve got my knife, my fork and my camera. I’m always scanning, waiting for something, anything.
ER Do you ever feel like you’re not living in the moment?
TS Absolutely. It comes with the territory, though, for better or for worse. I get to live this incredible life and travel the world with friends who I consider family, but at the same time, there is a disconnect. I don’t get to experience a moment the way they do. I feel like when they’re having the most fun, I’m working the hardest.
ER Has all your travel taught you any smart packing tips?
TS It’s tough because I never know where we’re going to end up. If we go to Turks and Caicos, I’m packing white tees and some bathing suits, but I don’t know if we’re going to wind up in London the next week and I’m going to need a raincoat. I’m constantly overpacking. I bring two massive Rimowas filled to the brim.
ER Since you’re on the road a lot, how would you describe your relationship with Toronto?
TS Toronto is always going to be my favourite place on earth. It’s home, regardless of where we go, but it’s a place that I see less and less of. We’re back and forth between L.A. and Toronto most months of the year, and then touring three, four, five months at a time. It’s also growing and changing rapidly, so I often come back and my favourite spot has closed down.
ER Does the city have an impact on your work?
TS Wherever you’re from, you’re affected by your environment. But when it comes to framing a photo, I don’t think it does. The films and photographs that I’ve been digesting my entire life, whether the VHS tapes that I stole from my dad’s friends when I was a kid or a photo book on the coffee table, are probably what affect my work more than anything else.
Carry‑on essential My JBL Flip speaker. Right now, I’m listening to a lot of King Krule, Popcaan and Blood Orange.
Travel hack Apply for Nexus. If you’ve ever landed at Pearson at the same time as three other flights when the air conditioning is busted, you’ll know why!
Dream seatmate Stanley Kubrick.
First travel memory Going to Georgian Bay with my dad and brother, and fishing in a small metal boat with a pirate flag on it.
Travel has the power to… Enlighten.