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Actors Haley Joel Osment (left) and Bruce Willis in a scene from The Sixth Sense.Courtesy Touchstone Pictures via Reuters

Do you remember where you were in 1999? More specifically – and more importantly – do you remember which movies you were watching in 1999? Ask any even half-hearted cinephile, and you’ll get an earful: The Matrix. Eyes Wide Shut. Magnolia. Fight Club. Election. Bringing Out the Dead. The Limey. Boys Don’t Cry. Toy Story 2. The Iron Giant. The Blair Witch Project. The Virgin Suicides. The Sixth Sense. And so, so many more – an almost unbelievable lineup that seems culled from an entire decade, not just a single 12-month stretch.

Yet 20 years later, 1999 has held its grip on the cultural imagination – there’s an entire podcast dedicated to going through each and every release – and can now be called a perfectly revolutionary year for cinema. Fresh filmmakers were changing the rules of the game (Being John Malkovich’s Spike Jonze), while veterans were working at the peak of their powers (The Insider’s Michael Mann). Even the seemingly mainstream fluff of the era (Deep Blue Sea, Dick, Galaxy Quest) feels miles above what Hollywood offers today.

To mark the 20th anniversary of the year everything changed, TIFF is launching 1999: Movies at the Millennium, a series that will screen 23 films from the era (many in 35 mm) at the organization’s Lightbox cinemas in Toronto. Ahead of the series' launch this Friday with Claire Denis’s masterful Beau Travail, The Globe and Mail’s Barry Hertz spoke with TIFF’s artistic director Cameron Bailey and TIFF Cinematheque’s senior manager Brad Deane about the year of living dangerously.

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Keanu Reeves (left) and Hugo Weaving in a scene from The Matrix.©Warner Bros/Courtesy Everett Collection/Warner Bros. via The Everett Collection

In the program notes for this series, Cameron, you note that “the best year in film” is kind of an arbitrary battle – some feel it’s 1939, or 1959. But what factors make 1999 deserve a retrospective today?

Cameron Bailey: Brad and I were both of the age then where we were paying attention to cinema in a pretty serious way, so we remember the films of that year well. And it was the year of Y2K, the year of millennial anxiety, where there was this fear of machines taking over our lives or hurting us in some way, so it felt like a signature year where there was a common zeitgeist. I was a critic then, writing my own year-end list, and it had The Matrix and Fight Club and Magnolia, and something in common is filmmakers questioning reality in some way, which fit in that anxiety about the clocks turning over.

Brad Deane: I remember how exciting it was going to a regular cinema at the time, and although I wasn’t as familiar with international cinema, there were all these incredible films from around the world in 1999, too.

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Nicole Kidman and Tom Cruise are shown in a scene from Eyes Wide Shut.The Canadian Press

It seems like 1999 was also rare in that critics were cognizant at the time of how important a year it was. I’m thinking of Jeff Gordinier’s column for Entertainment Weekly in November that year, where he wrote, “You can stop waiting for the future of movies. It’s already here.”

Bailey: For me there hasn’t otherwise been a year where, in the moment, I thought, “Oh yes, there’s something unique happening.” But 1999 was special.

Deane: I don’t think there’s been anything since. I’m waiting for another one.

Bailey: Let’s hope we know it when we see it. … Barry, were you, if I can ask, paying attention to movies in 1999?

Yeah, I was working in a movie theatre then, in high school. I remember actually having to wrangle my friends to go see Being John Malkovich, which was playing downtown at the Varsity [in Toronto]. I remember it because I almost crashed my parents' car on the way down. But among friends today, the year still holds that interest. People can’t seem to stop talking about it.

Bailey: It’s a confluence of a bunch of different factors, but there was also the common thread throughout most of them – The Matrix, Being John Malkovich – in which all these movies are saying that you can’t trust what you see. That’s kind of a new thing for a commercial art form to be telling its mass audience. There was this growing sense that the technology we created has gotten beyond us, and as a result we could no longer trust what’s in front of our eyes. If you love cinema, that’s an exciting notion, and these movies played it out so beautifully.

Looking back at the box office for 1999, it’s notable that only five of the top-10 highest-grossing films of the year were sequels or based on intellectual property. In 2018, all 10 top-grossing films are franchises.

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Brad Pitt (left) and Edward Norton are shown in a scene from Fight Club.Merrick Morton/20th Century Fox via REUTERS

Deane: I mean, look how difficult it is for many of the people who made these films in 1999 to get movies made today. David Lynch made his most normal film [The Straight Story] that year, and now he’s turned to a different form of filmmaking. The system has changed so much.

Bailey: One of the other things that’s happened is that film technology has changed. We’re presenting most of this series on 35 mm, but 1999 was one of the last years that film on film was so dominant. It was a turning point in a lot of ways. These films are almost holding that moment of time in amber, crystallizing it.

As we’re in awards season now, it’s interesting that the 2000 Oscars mostly focused on the 1999 films that we don’t talk about today: The Cider House Rules, The Green Mile …

Bailey: I think it was ever thus. That’s the benefit of hindsight. The films that were truly exceptional, truly revolutionary, are not usually the ones that win awards at the time. The movies that capture the attention of awards bodies at the moment satisfy the desires of the moment. With Beau Travail, not all the reviews were great at the time. But Claire Denis has now seen her reputation rise. Lynne Ramsay’s Ratcatcher, people are now catching up with that. And Fight Club has become legendary for all kinds of reasons.

Deane: Hopefully a lot of these films will get their honorary Oscar one day.

There are some great international titles here, but a lot of mainstream studio films in the series. How do you balance playing those titles at the Lightbox, which you wouldn’t normally consider as a place to see something like The Matrix or The Iron Giant.

Bailey: It’s all about context. We’re just wrapping up our Steven Spielberg series at the Lightbox, and there is no more commercial filmmaker than Spielberg. But if we can provide a context where you can see the films as they were meant to be seen on the big screen, and see the art of the film, not just the entertainment value, then that’s what we’re here for. The films change with the times changing, as well. We’re showing The Matrix, which was a remarkable leap forward for action cinema, but now it’s also an interesting example of how gender works in cinema. We’ll have Cael Keegan, a cultural theorist, coming to speak about that. It’s that kind of mutability to these films that’s interesting.

This conversation has been condensed and edited.

1999: Movies at the Millennium runs Jan. 11 through Feb. 10 at the TIFF Lightbox in Toronto (

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