by Heath Lynch, Contributing Writer

Welcome back to another Oscars: What If, our retrospective look at the Oscars!

We are barreling head first into the summer blockbusters season with plenty of fun and exciting movies on the horizon. It’s going to be a wild few months, full of explosions and popcorn. But before we get too excited about analyzing box office dollars, let’s look back at another award season long gone. As a reminder, with our Oscars: What If… series we look at categories the Academy Awards should be honoring, but for one reason or another, they aren’t, and we imagine what could’ve been regarding past Oscar seasons. Hopefully someday the Academy will do right by these creative talents, but until then we must do the Academy’s job for them. Let’s look back at the year Napster transformed the music industry with the release of its digital peer-to-peer file-sharing, Woodstock turned into a riot ending in a disastrous inferno, SpongeBob Square Pants premiered on Nickelodeon, and the Y2K scare took hold of the world. It is time to examine the films of 1999, celebrated at the Oscars in 2000. Let’s see what could have been!

Best Stunts and Choreography

Given to the best achievement in dance, stunts, related performances, and overall choreography.

And the nominees are… Fight Club, The Matrix, The Mummy, Star Wars: Episode I – The Phantom Menace, The World is Not Enough

And the winner is… The Matrix!

I mean… duh. Right? Next category?

But seriously, this was never a competition, and that’s for good reason. The Matrix redefined action filmmaking. It completely changed the industry, and almost entirely due to the incredible action, stunt work, and choreography. From introducing wire-fu to mainstream Western audiences, and changing the game in which it can be utilized, to incredible martial arts choreography, this film is on another level. Once you consider the invention of bullet time, you’re blowing people’s minds. You can still see the influence of this movie in action films to this day, and we probably still will for decades to come. There was never any other option here. The Matrix has to take home the gold for Stunts and Choreography.

Best Performance by Voiceover or Motion Capture

Given to the best off screen voice performance, or on screen motion captured performance.

And the nominees are… Joan Cusack as Jessie in Toy Story 2, Vin Diesel as The Iron Giant, Minnie Driver as Jane Porter in Tarzan, Trey Parker as Various in South Park: Bigger, Longer & Uncut, Tom Hanks as Woody in Toy Story 2

And the winner is… Joan Cusak as Jessie in Toy Story 2!

Now here’s an Oscar I couldn’t be more excited to award. Cusack has had such a wild, unique, and impressive career. Oscar-nominated herself, she’s never brought home the gold. Welp, today’s the day. Her portrayal of Jessie is one of the most heartfelt, moving, and memorable performances in voice acting. The range she displays, from the exuberance of reuniting with Woody to the sadness of telling her story about how she lost her human, is very impressive. There’s a solid argument that this should go to Parker due to the vast variety of characters he creates, but the emotional impact that Cusack gives us secures this Oscar win for her.

Best Performance by an Ensemble Cast

Given to the best overall ensemble cast performance.

And the nominees are… American Beauty, Girl, Interrupted, The Green Mile, Magnolia, The Talented Mr. Ripley

And the winner is… Magnolia!

I’m not going to lie, there were about 20 different films I was considering nominating in this category. I feel physically pained with some of the choices I had to leave on the cutting room floor. I guess that’s just another consequence of being one of the best years in film: You have a lot of the best ensemble years in film. Hell, even out of the five films I’ve nominated here, I could reasonably pick a different winner any given day. That’s how great they all are. But today we’re going with Magnolia. Paul Thomas Anderson’s third feature film is an ensemble epic for the ages. A narrative web packed with powerhouse performances that will knock you on your ass. Tom Cruise, Philip Baker Hall, Melinda Dillon, Philip Seymour Hoffman, William H. Macy, Julianne Moore, John C. Reilly, Jason Robards… I mean, the list goes on and on, and every one of them is exceptional. It’s not just that these are strong performances either. It’s that they’re such widely varied characters that have incredible chemistry with one another. It evokes the great Robert Altman ensemble films of old, such as Nashville. So while this award might go to a different film from an entirely different slate of nominees on a different day, on this day, I’m happy to award Magnolia.

Best Directorial Debut

Given to the best achievement in direction by a debut directing talent.

And the nominees are… Brad Bird for The Iron Giant, Sofia Coppola for The Virgin Suicides, Spike Jonze for Being John Malkovich, Gil Junger for 10 Things I Hate About You, Sam Mendes for American Beauty

And the winner is… Spike Jonze for Being John Malkovich!

Another really close category packed with tough competition. Again, on any given day I could give you a different answer here. Particularly, I was really tempted to give this to Coppola. But I’m going to give this to Jonze for the sheer craziness that he’s able to creatively control and deliver in a way few other directors ever could in Being John Malkovich. It’d be very easy for this Charlie Kaufman script to fly off the rails, but against all odds, Jonze pulls a rabbit out of his hat. From the aesthetics of the tunnel into Malkovich’s mind, the shrunken seventh and a half floor, and falling onto the New Jersey Turnpike, the is a visual treat. The bizarre characters, their quirky performances, and the design of their costumes and hair, all fall under the purview of Jonze, and he nails it. He gets the most out of his cast all throughout the film. In every way this can be a directorial challenge, this film seemingly is, but Jonze rises to that challenge and excels. He definitely deserves this Oscars gold.

Best Popular Film

Given to the best audience supported motion picture that earned a spot as one of the top 25 box office films of the year.

And the nominees are… The Blair Witch Project, The Matrix, The Sixth Sense, Star Wars: Episode I – The Phantom Menace, Toy Story 2

And the winner is… The Matrix!

It had to happen. It was the chosen one.

The Matrix was a phenomenon. A transcendent cinematic experience that changed the landscape of the entire film industry. Hollywood shook to its core as the ground beneath its feet trembled with astounding visuals, mind-blowing concepts, and adrenaline-filled action. Movies were never the same again, and neither were audiences. This masterpiece changed our perception of what was even possible with film, and how the theater experience could seemingly levitate you into the clouds. As such, audiences came out to see this in droves. The Matrix brought home a whopping $171.4 million at the domestic box office, and a worldwide total of $463.5 million. Now, that may not seem very impressive when Star Wars: Episode I – The Phantom Menace came out the same year and brought in $431 million domestically, let alone globally, but we must consider a few factors. We have to keep in mind that, at the time, Star Wars was the most beloved film IP in the world. That it was getting its first film in 16 years and there was a fervor for this film that was insatiable. That it was a PG film made to bring in more audiences, particularly kids. And, most importantly, that this Oscar is for the Best Popular Film, not the Most Popular Film.

When we look at things through this lens, and see that The Matrix brought in audiences in droves (the highest grossing R-rated film of the year by a wide margin), and factor in how this changed the industry and went on to spawn a franchise all of its own, this becomes no contest. In fact, when we consider awards accolades, the decision becomes even more clear. The Matrix was nominated for four Academy Awards this year. Best Film Editing, Sound, Sound Effects Editing, and Visual Effects. And you know what? It swept the board, going a perfect four-for-four, even beating out The Phantom Menace in three of those categories (the only categories it was nominated for, meaning The Matrix completely knocked George Lucas off the board). And if we’re really being honest with ourselves, there should’ve been more noms and possible awards for The Matrix. How it wasn’t nominated for Best Original Screenplay over Topsy-Turvy is beyond me. Don’t get me wrong, Topsy-Turvy is a good film, and a great screenplay, but better, or more original, than The Matrix? C’mon…

Burying the lede, the only real competition here is The Sixth Sense, a flick that made $293.5 million domestically, was nominated for six Academy Awards, including Best Picture, and had the world talking about how they see dead people. There is a valid argument that it should be the true winner, especially if this Oscar was awarded at the time. But, this is my column, and I have the benefit of 20/20 hindsight. So, for all the reasons listed, plus its endearing legacy, I am ever so proud to award The Matrix with the Oscar for Best Popular Film.

Thanks for joining me on another trip down memory lane to see what could’ve been! We got to reminisce about one of the greatest years in the history of cinema, including Kubrick’s final film, a flick whose rules we cannot talk about, and a mind-blowing sci-fi action flick that changed movies forever. Be sure to come back next month when we look at films like Almost Famous, Crouching Tiger, Hidden Dragon, and Gladiator, as we return for the Oscars of 2001, celebrating the films of 2000!

You can read more from Heath Lynch, and follow him on Letterboxd