24 Years of the Toronto Film Festival in 19 Unforgettable Photos

From Oprah and Clooney to Denzel, TheWrap’s Jeff Vespa has photographed them all

Oprah and George Clooney, Toronto Film Festival
Photo by Jeff Vespa

You’d be forgiven if you thought the above photo was taken backstage at a rehearsal for the Oscars. After all, the joyful colliding of two supernovas does not happen just anywhere, anytime down here on earth. But this particular close encounter took place at the 2009 Toronto Film Festival, at the premiere for “Up in the Air.”

Behind the scenes at the Ryerson Theatre, George Clooney and Oprah Winfrey found themselves sharing the same space and posed for TheWrap creative director Jeff Vespa.

“This is the typical kind of Toronto happening where I’ll get a call and they’ll be like, ‘Get over here right now! Because George Clooney is going to meet with Oprah,” Vespa said. “You have to race over to one of the theaters, and you rush backstage and wait around until the moment happens.”

Vespa has documented countless such moments throughout his career, at Toronto, Venice and elsewhere. To celebrate the Sept. 7 kick-off of the 2023 film festival chez our neighbors to the north, he selected the following photos from the past 24 years.

George Clooney, Oprah Winfrey, Gayle King and Ivan Reitman (2009)

Snapped at the same premiere, this unposed shot shows Clooney and Winfrey sharing a laugh alongside Gayle King. In the background, hometown hero Ivan Reitman, who produced “Up in the Air” — the film was directed by his son, Jason. “This was a huge deal,” Vespa said.

Bruce and Gwyneth Paltrow (2000)

Vespa took this sweet photo of father and daughter at the premiere for “Duets,” which Bruce Paltrow directed and in which Gwyneth Paltrow starred. “Gwyneth and her dad — it’s a cool shot of the two of them together. They look happy,” Vespa said.

Paltrow fille had won her Best Actress Oscar for “Shakespeare in Love” the previous year, so she was, as Vespa noted, “already a big deal. And I just remember feeling like, ‘Wow, it was just great to get her at that point.’” (Bruce Paltrow died in 2002.)

Ben Affleck and Maya Rudolph (2000)

Here, Ben Affleck and Maya Rudolph stop for a quick frame at the “Duets” premiere. This was the Ben Affleck-Gwyneth Paltrow dating era, which explains his presence at the event. As for Rudolph, file this away for your next trivia night: In addition to a small acting role as the Omaha Karaoke Hostess in “Duets,” she was the film’s music supervisor. (She and Gwyneth were also friends growing up.)

Heath Ledger (2002)

Before “Brokeback Mountain” and “The Dark Knight,” Heath Ledger starred in “The Four Feathers,” a period adventure drama directed by Shekhar Kapur that galloped into the 2002 Toronto festival. Vespa took this photo of the actor sheepishly signing autographs at the movie’s premiere.

“I like this because to me, this is Heath,” Vespa said. “He was not in love with being a celebrity and didn’t like doing press. The expression tells it all. But he was so great about it. He was a good guy. A great dude.” (Ledger died in 2008.)

Iggy Pop and Cate Blanchett (2003)

Director Jim Jarmusch brought together these two giants. The punk rocker and the Oscar-winning actress appeared as part of separate vignettes in Jarmusch’s 2003 black-and-white gem “Coffee and Cigarettes,” which filmed over the course of 17 years. “I just thought this one was fun,” Vespa said. “How many times do you see Cate Blanchett with Iggy Pop?”

Alec Baldwin and Sarah Jessica Parker (2000)

“It’s hard to get candid pictures, so I think they were just goofing off with me,” Vespa said with a laugh as he thought back to this shot of Alec Baldwin and Sarah Jessica Parker at a party for the David Mamet film “State and Main.” “They were pretending to do something or act like they were having an interesting conversation.”

To the left of Baldwin is costar Julia Stiles, whose career was on the rise. At the far left is Clark Gregg, who was not nearly as well known back then. “This is a funny picture because Julia Stiles, everybody thought she was going to be the next big thing. And then Clark Gregg, for years, I didn’t know who that was. I was like, ‘Who is that guy?’ I kind of recognized the face but I didn’t know who he was and it really got to me. I was like, ‘I have to caption the picture!’”

The photo below shows Parker outside the same party. This was during peak Carrie Bradshaw/”Sex and the City,” so naturally, there are cameras following her every move. “I like it because it’s a really great fashion moment,” Vespa said. “And I think it’s cute.”

Frances McDormand and Patrick Fugit (2000)

“This one is just great because they’re from ‘Almost Famous,’ of course, and it’s just really fun,” Vespa said. “It’s a great picture and seeing them so young is pretty amazing.”

Brendan Fraser (2004)

Eighteen years before he took home an award for his performance in “The Whale” at the 2022 Toronto festival (the first of many prizes he’d collect for that performance), Brendan Fraser attended the fest in support of “Crash” — Paul Haggis’ drama chronicling crisscrossing lives in L.A. that went on to (controversially) beat “Brokeback Mountain” for Best Picture at the Oscars.

In 2004, Fraser had already starred in “God and Monsters” and “The Quiet American,” but was still primarily associated with “The Mummy” franchise. So “Crash” was a chance to show his dramatic chops. “He’s just really happy here,” Vespa said. “That was one of those moments where people were very excited about the movie, where you could feel like, wow, something is happening here. To me, this picture embodies that.”

The “Memento” Gang (2000)

Vespa recalls taking this photo at a dinner for “Memento,” the mind-scrambling indie directed by a young British filmmaker named Christopher Nolan. Back then, not all festival parties were mega-events attended by hoards of industry and press. This was one such intimate gathering where cast members Guy Pearce (whose starring role as a tattooed amnesiac was his breakthrough), Carrie-Anne Moss, Joe Pantoliano and Kimberly Campbell posed with Nolan.

“It wasn’t a ton of people — just cast, top producers and some studio execs,” Vespa said. “And that’s where you get these cool moments. Obviously, there was a lot of talk about ‘Memento’ from the beginning.”

Denzel Washington and Ethan Hawke (2001)

Antoine Fuqua’s “Training Day” had its North American premiere at Toronto, where stars Denzel Washington and Ethan Hawke convened for the press conference captured in this frame.

“I thought it was a nice, fun moment,” Vespa said. “Press conferences were in the hotel ballroom-type spaces, but this was tiny. We were all super packed in there and it was super hot and the line was way out front of the door. I had to get in quickly to get a good spot.

“Ethan was a big actor at that point, but it was still kind of a huge deal, him showing up in this movie. And it was a great film.” Washington went on to win the Best Actor Oscar for “Training Day,” while Hawke earned his first-ever nomination, for supporting actor.

Daryl Hannah and Rose Byrne (2000)

Rose Byrne was just 21 when she went to the 25th Toronto International Film Festival to promote the Australian indie “The Goddess of 1967,” directed by Clara Law. In this photo, she chats with Daryl Hannah, who attended the festival for the world premiere of the drama “Dancing at the Blue Iguana.”

David Lynch and His “Mulholland Drive” Stars (2001)

After premiering at Cannes, David Lynch’s thriller about unsettling things happening to an aspiring Hollywood actress traveled to Toronto to bend some more minds. It was this film that put Naomi Watts firmly on the A-list. Vespa had known Justin Theroux for years by then and met Watts previously.

“I did portraits of them in Cannes, and then I saw them in Toronto and it was just really exciting, because the [buzz] from Cannes to Toronto started building with the film.” Vespa took this photo at the party following the movie’s North American premiere.

“Of course I was taking a picture of them for the event, but it was more for me just a fun moment, more like a friend moment. I wanted to capture this moment of all of them together, because it was a really great time. I love it. It brings me back there when I see it.”

Anthony Mackie, Jeremy Renner and Brian Geraghty (2008)

At the 2010 Academy Awards, Kathryn Bigelow’s Iraq War drama “The Hurt Locker” beat “Avatar” for Best Picture — and Bigelow became the first woman to win Best Director. But almost two years before that, the gritty film about a traumatized bomb disposal team had its North American premiere at Toronto.

Though Jeremy Renner was still several years away from joining the Marvel Cinematic Universe as Hawkeye, Vespa knew him from crossing paths in Los Angeles. He hadn’t heard much about “Hurt Locker” before attending the screening (not many people had), so when he finally saw it, he was floored. The film earned raves and Renner became a breakout star. (Criminally, Mackie did not receive as much attention as his costar, who was nominated for a supporting actor Oscar.)

“Every person wanted to meet Jeremy,” Vespa said. “Robert Duvall would tell me, ‘Hey, you’re friends with that guy. I want to meet him.’ Literally, Robert Duvall told me that. People were tripping over themselves to meet him. It was just such an incredible moment.

“And, you know, because he’s been around for so long, he just never changed. It wasn’t really overnight success. It was the 10-year, 15-year overnight success. And the guy just stayed the same. He still has to this day. He’s a great guy.”

Joe Russo and Anthony Russo (2002)

Vespa became acquainted with the future powerhouse directing/producing brothers in 1997, when he saw their black comedy “Pieces” at the Slamdance Film Festival, where he worked at the time on the festival programming team. “Joe is in the film. This guy’s like a young De Niro in the movie. It’s unreal,” Vespa said.

Vespa became an instant fan of the Russos’ film — and so did Steven Soderbergh, who eventually produced their film “Welcome to Collinwood.” The brothers’ first major studio movie played at the 2002 Toronto festival, which is where Vespa took this picture.

“This one is just hilarious,” he said, laughing. “Look at these guys. I mean, they’re babies — and look at the outfits! I really wanted to be there and support them and now, of course, they’re two of the biggest directors in the world.”

Philip Seymour Hoffman (2000)

“This is my first picture of Philip Seymour Hoffman, which I love,” Vespa said. “It’s such a great picture of him. I was just kind of like, ‘Hey, man. Can I take a picture?’ And he was like, ‘Sure.’ I literally took one frame.”

Jim Jarmusch (1999)

“This one is my very, very first portrait I ever did in Toronto,” Vespa said. Indie auteur Jim Jarmusch was in town for the North American premiere of “Ghost Dog: The Way of the Samurai.”

“I love Jarmusch. And, you know, in ’99, he was such a big deal in the independent film world. I was a huge independent film fan.”

The “Bobby” Team and Jeff Vespa (2006)

Emilio Estevez’s film “Bobby,” about the assassination of Robert F. Kennedy, played at the 2006 fest — where Vespa hopped into the frame you see above.

“When I was a kid, I would watch his movies and be like, ‘I know if I met Emilio Estevez, he’d be my friend,” he said. “And eventually I did become friends with him. It was pretty amazing. He was actually at my wedding.

“But I love this one because he told me that ‘Bobby’ was going to Venice and Toronto and he hadn’t done publicity for years. I was like, ‘Oh my God, dude. I’m gonna be there. I’ll be there the whole time.’ And it was just a cool thing — really fun time with the whole cast. This was after the ‘Bobby’ after-party, and it’s one of my favorite pictures of all time because it’s so much fun. I just love the vibes.”