Sandra Bullock getting into a black car after the Vanity Fair Oscars after party


Over 30 years, George Pimentel has photographed almost every imaginable A-lister—including Taylor Swift, Jennifer Aniston, Beyoncé, Adam Sandler and Sandra Bullock

By Maddy Mahoney| Photography by George Pimentel
| September 1, 2023

Before George Pimentel was a bona fide celebrity photographer, he was a 12-year-old kid working in his father’s photography studio in Little Portugal. Pimentel was doing terribly in school—he had a hard time focusing on math and science—but he knew how to shoot. Through the late 1970s and 1980s, he spent Saturdays helping his dad photograph weddings in church basements. Every spring, they’d shoot rows of ten-year-olds as they lined up for first communion.

Around the same time, his older sister Maria was becoming a movie buff. Her permission to go to the theatres, however, hinged on her youngest brother tagging along. “I grew up with Scorsese; I was tormented by Hitchcock,” says Pimentel. “I loved movies. But my favourite was The Godfather. Robert De Niro was my idol.”

Related: Twelve striking photos that capture life in 1970s and 80s Toronto

So, in 1993, when his sister offered him a ticket to see De Niro’s A Bronx Tale at the Elgin Theatre, he immediately agreed—even though he’d never heard of the Toronto International Film Festival, where it was playing. He brought along his Hasselblad film camera, and when the bouncer spotted it, he directed Pimentel to the media section. “There were no cellphones back then,” Pimentel says. “If you had a camera, you were pretty much a professional.”

When De Niro stepped out of his silver limousine, Pimentel was star-struck. Minutes later, the actor and the rest of the photographers entered the theatre, but Pimentel was denied entry—he didn’t have any credentials. He got lucky, though: De Niro came back out after all the accredited photographers had cleared away, and Pimentel snapped his photo. “By the time I was printing it out in the dark room later, I knew I wanted to keep doing this,” he says.

Pimentel's first celebrity photo was of Robert De Niro at the TIFF premier of A Bronx Tale
Robert De Niro, A Bronx Tale premiere at TIFF (1993)

Over the next 30 years, Pimentel worked his way up from streetside photographer to receiving official invitations to photograph Hollywood’s glitziest events, including the Oscars, the Cannes Film Festival, the Met Gala and, of course, TIFF. He’s captured almost every imaginable A-lister, including Beyoncé, Tom Cruise, Madonna and Taylor Swift, and his work has appeared in People, Vanity Fair and Vogue. (He’s also a contributing artist to Toronto Life.)

Now, the photographer-to-the-stars—who still works out of a studio on Dundas West—is showcasing a collection of his images in “30 Years of Red Carpet Style with George Pimentel,” a retrospective presented by Yorkdale Shopping Centre. The exhibition is open to the public from September 5 to 30. Here, Pimentel shares the stories behind 18 unforgettable photos from the show.

Tom Cruise at a TIFF press conference in 1998

Tom Cruise, TIFF press conference at Sutton Place Hotel (1998) “This is the nicest guy in Hollywood. Tom is someone who loves fame, and he works hard at it—he shows up an hour before premieres to sign autographs; he embraces it. He makes you feel like a million bucks and looks at you when you shake his hand, treats you like a normal human being. That’s all I need to know. He’s a true star.”

Jennifer Aniston, signing autographs for fans at TIFF

Jennifer Aniston, Management premiere at TIFF (2002) “My Jen. She’s my favourite. I grew up watching Friends, and it helps that she’s so sweet and completely down to earth. She’s a real actor. I really thought Brad Pitt was completely in love with her. In some of the photos I have, you can see it in his eyes. But, in the end, of course, it didn’t work out.”

Adam Sandler points at Pimentel as he snaps his pic

Adam Sandler, Punch-Drunk Love premiere at TIFF (2002) “Adam may not look like a Leonardo DiCaprio or a Brad Pitt, but he’s got those comedy chops from when he started on SNL. He makes you feel like he’s your best friend, and he’s just completely himself. I was such a huge fan. I remember I just yelled, ‘Hey, can I get a quick photo?' And then he pointed right at me.”

Madonna looks over the shoulder as she leaves a restaurant with her security

Madonna, TIFF after-party at Nector (2005) “In the ‘90s and early 2000s, Madonna was our Taylor Swift. I made a deal with her security team for this one: if they brought her out the front door of the restaurant, I’d tell all the autograph collectors that she wasn’t signing anything. All she’d have to do was wave. They agreed, and when she did, I yelled out, ‘Madonna, can I get one over the shoulder?' She gave that to me.”

Angelina Jolie walking past flash bulbs and cameras at TIFF

Angelina Jolie, TIFF (2007) “There were a few years where Angelina showed up at every single festival. One time, in Toronto, the fans actually pushed one of the fences down to see her, so police had to stand there holding it up. Now, she doesn’t do much press. I wouldn’t even ask her to do anything. I would never make someone pose if they didn’t want to.”

Sandra Bullock getting into a black car after the Vanity Fair Oscars after party

Sandra Bullock, Vanity Fair Oscar party (2010) “People always think this was taken when she was coming into the party, but it was actually when she was leaving. That’s when I get my most artistic photos. There’s arrivals, where everyone is all proper and all business, but then there’s departures. Everyone has to leave and get into a car at some point, right?”

Bradley Cooper getting swarmed by fans before a premiere at TIFF

Bradley Cooper, The Place Beyond the Pines premiere at TIFF (2012) “Bradley arrived early for this one, and everyone just mobbed him. I love a good fan photo, and this one was lucky because he’s right in the centre and there’s nothing blocking him. I looked at this photo a lot during the early days of the pandemic. I worried that we’d never get to have this again.”

Amy Adams walking up the stairs into the Academy Awards

Amy Adams, Academy Awards (2013) “This was the first time I covered the Oscars, and I made a no-no. I was there with Variety, and I was just supposed to shoot the executives. But the celebrities kept walking past me. I couldn’t help myself. Whenever they went up the stairs, I’d run out and get their photo. Apparently, no one had ever been photographed on the stairs before. I got in a bit of trouble for that.”

Beyoncé walking up the red carpeted stairs into the Met Gala

Beyoncé, “China: Through the Looking Glass” Met Gala (2015) “Beyoncé always shows up fashionably late. Everyone asks me, How is there no one else on the carpet? That’s unheard of at the Met Gala. Well, Beyoncé arrived 90 minutes late, and all the photographers are suckers because we have to stay and she knows it.”

Lady Gaga slowly removes a black veil on the red carpet at TIFF

Lady Gaga, A Star Is Born premiere at TIFF (2018) “This was my most memorable red carpet. Lady Gaga came right up to me and whispered in my ear, ‘When should I take off the veil?' She really wanted to make a moment. I told her to wait, and she listened. It was surreal—it felt like it was just me and her. Then, when I told her to do it, she looked right at me and slowly lifted it up. Everyone went nuts.”

Brad Pitt and Leonardo DiCaprio in black suits and bowties

Brad Pitt and Leonardo DiCaprio, Once Upon a Time in Hollywood screening at the Cannes Films Festival (2019) “I’m always looking for a James Dean–style photo, and in this one I got two James Deans. Don’t ask me how it is that they’re looking at me—I was 200 feet away. I won’t be able to get one like this ever again, not with them together. They’re getting older, and Leo doesn’t like having his photo taken.”

Jennifer Lopez looks straight at the camera while strutting the red carpet

Jennifer Lopez, Hustlers premiere at TIFF (2019) “J.Lo knows what she’s doing when she walks the red carpet. Don’t tell her what to do, okay? Don’t even talk to her. After I took this, I told her team that it would be online within minutes. As soon as she was done on the carpet, I heard her say, ‘Where’s my phone?' She put the photo on her Instagram right away.”

Nicole Kidman and Keith Urban walk hand in hand

Nicole Kidman and Keith Urban, Screen Actors Guild Awards (2022) “I love them. That’s not fake love between them, either—they’re the real deal. And Nicole is a star. The world has changed—reality TV and Instagram came on the scene. We love our Kardashians, but Nicole represents old Hollywood to me. I showed them this photo. I actually ended up sending it to them. Keith really liked the dramatic lighting.”

Will Smith and Jada Pinkett Smith, on the night of the slap

Will Smith and Jada Pinkett Smith, Academy Awards (2022) “This night was the craziest moment of my career. After the red carpet, I was watching the ceremony from the press room. I was eating some shrimp cocktail and looking at the screen, and suddenly I saw Will Smith go over and slap Chris Rock. You know, in celebrity culture these days, your fans are your employers. Will Smith broke all the rules. He jeopardized his fan base.”

Zendaya looks over her shoulder in a shimmery silver dress

Zendaya, Academy Awards (2022) “Zendaya is the perfect example of young Hollywood class. Every time I take a photo of her, it sells. She’s so kind, and she follows instructions. She could be in any situation, and if you ask her nicely, she’ll turn it on and give you what you’re looking for.”

Jennifer Lawrence stands beside a security guard at TIFF

Jennifer Lawrence, Causeway premiere at TIFF (2022) “It’s hard for people to understand what it takes to get a photo like this, to have everyone cleared out. It’s nearly impossible. I constructed this completely; I had to tell everyone to get out of the way. But I like the security guard standing there. It gives it context.”

Taylor Swift at TIFF 2023, where droves of people showed up to try and spot her

Taylor Swift, TIFF (2022) “This was the ‘In Conversation With’ event where Taylor was discussing the ‘All Too Well’ music video. She was being mobbed, but I was able to get close to her because I was working for TIFF and I had a relationship with her publicist. I shot some of her last Canadian tour: the stops in Ottawa, Toronto and Montreal. Taylor Swift is the nicest person, hands down.”

Jennifer Coolidge walks off stage after presenting a SAG award

Jennifer Coolidge, Screen Actors Guild Awards (2023) “This is a good example of someone who’s been in the business for so long and then finally gets her big break. People finally recognized her, and I’m such a big White Lotus fan. This was right after she’d presented an award. She had literally just walked off the stage.”


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