Caitlin Cronenberg Shares the Backstory Behind Some of Her Most Famous Celebrity Portraits

She's shot everyone from Sarah Gadon and Meghan Markle to Drake and JLo.

The Endings, a photo series by Toronto-born photographer Caitlin Cronenberg and art director Jessica Ennis, was shot over the course of seven years, culminating in a 2018 book by the same name. That series, which features Hollywood A-listers like Keira Knightley and Julianne Moore as characters caught up in the emotional tumult of heartbreak, is now being developed into a TV show by Sony Pictures Television. Select photographs from that series are now a part of the Broadview Hotel’s permanent collection, greeting guests at the elevator banks on each floor, and peering down from the walls of the Toronto hotel’s bar and restaurant. We caught up with Cronenberg as she walked us through the hotel’s acquisition of her work, and then sat down with her to get the lowdown on some of the most iconic celebrity portraits she’s shot in recent years.

Sarah Gadon

This is Sarah’s “story” in The Endings, and we shot it out by Jess [Ennis]’s parents’s place in Thornhill, which was very fun. The story was that she’s going through her boyfriend’s breakup box and smashing and burning things. And it was actually pieces from Jess’s actual ex-boyfriend’s box, like letters they had written her and CDs, that we used. So it was like a catharsis in a way for her, which was kind of amazing. But the story was that she runs into the woods and sets this thing on fire. So we took our little team and went down into the wooded area in Thornhill on a warm summer night, and had her set this box on fire and this is the final image of her walking away from it. She’s the greatest subject of all time, flinging herself down hills and letting us put fake blood all over her and shooting into the wee hours of the night, smoking terrible clove cigarettes as props and smashing CDs in the middle of this cul de sac in Thornhill. It was really fun. And since then we’ve done so many shoots together and I’ve done stills on a bunch of films that she’s been in. Every time we shoot her, it’s like a totally new experience.

Robert Pattinson

This was one of my favourite shoots. This was when Rob was really at the beginning of his breakaway from the Twilight situation. I had done three or four films with him, doing stills—so we knew each other pretty well by this point. But you know, he’s a shy person… I find that a lot of actors are actually quite shy when it comes to photo shoots because it’s a very different experience. They don’t have a character to play. So what I like to do when I shoot actors, even if it’s for an editorial, like this one for L’Uomo Vogue, I like to give them a backstory. This was styled by Rushka Bergman, who is the most creative stylist I’ve ever worked with. We drove out to Joshua Tree to do sort of this Mad Max in the desert. All of the over-the-top jewellery and the spikes and the eye patches was all Rushka, she’s the only person who’d say, ‘You’ve got one eye patch on, let’s put on a second eye patch.’ And Rob was pretty open [to it]. He was kind of laughing as he put on the leather pants and saying to himself, ‘do I look ridiculous?’ But then as I showed him the images as we were shooting, he got really comfortable. I mean, he was hot in it, because we were in a desert and it was a very hot day in the desert. But he did so well. I was very impressed by him.

Schitt’s Creek

I have been lucky enough to work with these guys every year since season one, doing their gallery shoots, which is their character shots and promo shots. Watching it blow up… I’m so proud of Dan and Eugene. It’s just an incredible thing, the fact that they’ve been recognized internationally and the response that they’re getting. The show itself is so special. It’s so funny. It’s so inclusive. It’s all of these things that we really desperately need. I didn’t know them [before working with them]. I think I had probably crossed paths with Dan when he was at MTV, but not in any serious way. And I hadn’t met Eugene or Catherine, who I consider to be Canada’s parents. I didn’t know Annie either. But they’re such a creative bunch. We’d just be laughing all day long—they are so funny and so brilliant. And they’re like a family, they’re very welcoming. So even though I was only in there for a few days each season, I always felt so welcomed by them. You get to feel like you’re a small part of something that they’ve built that’s so impressive and so wonderful.

Jennifer Lopez

I don’t even remember [shooting her] because I blanked out and then when I looked at the photos later I was like, ‘Oh good.’ JLo is the most magnificent creature I’ve ever seen in my entire life. She’s just so stunning. You look at her face and you’re like, ‘How? How? I don’t understand.’ My baby started kicking while I was shooting her, for the very first time. It’s like he knew that it was JLo. I was so nervous. But she’s very professional. When you’re shooting during the film festival [TIFF], everybody is really business. I had the whole cast of Hustlers in there, doing singles one at a time. They come in, they get fixed up, just quick touch-ups, and then you have five minutes and then their publicists yell at you and you bring in the next person. I was just thrilled that I got time with each of them because they’re an amazing, fun cast. But there’s sort of nothing like her, she exceeds all expectations.

Billie Eilish

What can you say about Billie Eilish? She is the 17-year-old that I wish I had been. Just her talent, the way that she is working so hard and I’m seeing this because I’ve shot her twice. Once for this Spanish clothing company, Bershka, and I just shot her again for Beats. She’s so hardworking. She’s so focused and she has such good ideas. Even just walking on to set, she knows what she wants, she knows how she wants to be styled, she knows how she wants her outward persona to be and she knows how to protect herself. And I think that’s so important when you’re that young and when you’re blowing up the way that she is. She won’t do anything that feels not like her true self. And I respect that. It’s rare to find people who are like that. I think she’s a great role model for young women. She is showing [them] that there’s no one way to be. And she’s humble and down to earth, the kind of person who’ll blush when you tell her you love her work. There’s just something so real about her but also intimidating ’cause I’m like ‘I can’t believe what you’ve accomplished already.’

Meghan Markle

We did ‘A Day in the Life with Meghan Markle’ for Holt Renfrew about seven years ago. It was a one-day shoot in which we just kind of hit her favourite spots in the city to highlight where she would spend her days off [from filming Suits]. She’s another very down to earth person—someone who you could be very chill with and, like, hang out with every day. Very fun, very funny. People on the street recognized her, because Suits has always been huge. Everyone knows that it shoots here and I think everyone’s always excited to see someone who’s kind of made Toronto their home. She stopped and took photos which was really nice and not everybody will do that. I think people really appreciate little gestures like that, that make their day and are not that big of a deal for her. It was a great experience, really fun.

Drake

The Drake shoot was awesome. It was 2016; I did the cover of Views and the interior booklet over a three-day shoot in April. My kid was four months old and on set with us, it was totally insane. It was intense because they wanted so many setups and had all these great ideas. We had a PDF of 11 different locations and sets that they wanted us to find and build in like, two and a half weeks. But we made it work. Everything turned out so well. Drake’s a total pro—he shows up on set, knows exactly what to do. I mean, he was an actor, so he’s easy to direct. And he’s another person who really has a strong sense of self and knows how he wants to project himself, which was really great. And also as a fellow Torontonian, born and raised, it was fun to explore the city with him and really celebrate the city. For this shot, he wanted kind of like a ‘King of Toronto overlooking the city’ vibe. It was so moody that day because of the snow and because of the sky; it’s very reminiscent of Toronto winters and gives you that real city grit. There’s a great mood to it and it’s a mood that we all know so well from so many months in a year. I really loved that. It’s beautiful.

Carrie Fisher

This was a great day. Carrie Fisher had us over and I did portraits of her and her dog for a project that I’ve been working on for a while about celebrities and their pets. I had an amazing time with Carrie and it’s just devastating what happened. It’s sort of unthinkable. She was an incredibly intelligent woman, like mind-blowingly brilliant. So quick, so witty. And the way that she interacts with you is like that—it’s like the combination of the best of all of her characters. I really felt connected to her. Her love of dogs rivals my own love of dogs. That’s Gary Fisher, her dog, who was her prize possession, her love. She’d go for a massage and he’d get up on the table with her, he walked all the red carpets with her. Her home was so eclectic—she has a Christmas tree up all year round and crazy Star Wars props. It was an amazing little bit of insight into her life. She was a super, super special person.