Why 1999 was the best year in movie history

All week long our writers will debate: Which was the greatest film year of the past half century? Check here for a complete list of our essays.

The end of the 1990s was the end of an era on the big screen. The independent filmmaking movement that started the decade had taken full bloom and infiltrated the business. Major studios had begun to jump headlong into the “dependent” game, amping up prestige product and utilizing the awards season as a marketing tool. The blockbuster landscape at the summer multiplex had been interesting, full of original concepts (good and bad), but something else was on the way – a new overlord in the business of film, and one that would more or less make the age of the movie star (at least as we had come to know it) a thing of the past.

For those reasons and a slew of others, I consider 1999 to be the greatest film year the cinema has seen. And that's not necessarily “greatest” as in value judgment. For as many exciting things that were happening creatively, equally alarming things were happening to shift the landscape of this industry. Whether you consider them for good or bad is up to you, but their impact is unmistakable, and any year that can lay some claim to that kind of a shift cannot be denied.

So let's start there…

We're in the midst of “Star Wars” madness right now as director J.J. Abrams and producer Kathleen Kennedy prepare to unleash “Star Wars: The Force Awakens” onto the world in December. Back in May of 1999, “Star Wars: Episode I – The Phantom Menace” proved the insatiable appetite for this franchise, which had been starved throughout most of the 1980s, was still very much alive. It was more or less tested and confirmed through the expanded universe materials of the 1990s, books, comics and video games stoking the flames. In 1993, filmmaker George Lucas announced his intention to revisit the world he created with a new trilogy, and a packaged re-release of the original trilogy in 1997 further established that the audience was ready and willing. It was an exciting time, and it may well have signaled the beginning of a new bedrock philosophy in Hollywood: brand appeal.

Before 1999, when you looked at box office results, they were dominated by movie stars. Tom Cruise, Julia Roberts, Mel Gibson, Tom Hanks, these were the draws. Slowly thereafter, particularly as the industry turned to the world of comic books for fodder (“Blade” was a bit of a testing ground in 1998 with 2000's “X-Men” and 2002's “Spider-Man” soon to follow), intellectual properties and preexisting material began to drown out those big names. In 2011, finally, every film on the list of top 10 domestic grossers was either a sequel or, in the case of “Thor,” part of an interlinking cinematic universe spread across multiple properties.

You can probably trace a lot of that back to “The Phantom Menace.” It was a huge part of changing the boardroom thinking of this business and morphing it into what we have today.

With all that in mind, I also find it sort of fascinating that my own favorite entry from the year, Michael Mann's “The Insider,” dealt so heavily in corporate synergy at the expense of all else. This was three years after the Telecommunications Act of 1996 allowed for the streamlined, everything-is-owned-by-six-companies world we live in today (which led to movie studios being gobbled up by conglomerates and, not to oversimplify, fertilize a current environment that has entities like Disney aiming for multimedia brand extension on a staggering scale).

Of course, over-conglomeration is nothing new in Hollywood. After all, Mel Brooks sent up Paramount corporate parent Gulf + Western as “Engulf and Devour” in 1976's “Silent Movie,” a full year before anything called “Star Wars” entered the public consciousness. But there's no mistaking the sense of liftoff that occurred at the end of the millennium.

Beyond all that, 1999 was just so rich. Going back to the independent filmmaking movement, those rebels were fully coming into their own as the new titans, with a list of works to rival any “great year.” Paul Thomas Anderson gave us the bold and dramatic interconnectivity of “Magnolia.” David O. Russell offered up the first real dissection of the Gulf War with “Three Kings,” a story of honor in the face of greed. DreamWorks finally caught its stride with an exciting new filmmaker (Sam Mendes) at the helm of “American Beauty.”

  

Moreover, masterpieces seemed to come left and right – Anthony Minghella's “The Talented Mr. Ripley” (latter-day Hitchcock at its finest); Brad Bird's “The Iron Giant” (animation with dramatic heft before Pixar came to own that niche); Alexander Payne's “Election” (a witty satire announcing a vital new voice); Spike Jonze's “Being John Malkovich” (the arrival of screenwriter Charlie Kaufman, willfully bending the form into something new); David Fincher's “Fight Club” (also tying into the theme of corporate overload). The list is endless.

In addition to all of this, the greatest practitioner of the form (OK, “in my opinion”) gave us his final film as well. And indeed, “Eyes Wide Shut” was right up there with director Stanley Kubrick's finest work. I might add that, at a time when their cachet was (as noted) starting to wan, it was one that intriguingly dealt with our perspective of movie stars, given his casting choices of Tom Cruise and Nicole Kidman.

What's also interesting about “Eyes Wide Shut” is something my colleague Drew McWeeny has noted before. “The Thin Red Line” hit in December of 1998 (and went wide in January of 1999), while of course “The Phantom Menace” landed in May. That means there was one a moment in history when Terrence Malick, Stanley Kubrick and George Lucas – probably the least prolific top tier filmmakers around – were working on a movie at the same time. Craaaazzzyyy.

Elsewhere, “The Blair Witch Project” was an equally notable piece of this puzzle. The found footage genre didn't start there, but it certainly became viable on a larger scale as soon as that micro-budget flick raked in over $100 million at the box office. As well, the film utilized an innovative internet marketing campaign at a time when that little tool was first really being explored for such purposes. Another film tapped into the online world to reach audiences, too, and we would be remiss not to mention it.

Andy and Lana Wachowski's “The Matrix” is, for many, the identity of 1999 in film. The ultimate dramatic representation of a techno-world on the brink of change, that March release seemed to be the spark that ignited everything else that year. “Neuromancer” author William Gibson called it “arguably the ultimate cyberpunk artifact,” and indeed, when the story of 1999 is told, “The Matrix” may well be its centerpiece.

There are things I haven't mentioned that of course deserve notice. I consider “Sleepy Hollow” to sort of be the ultimate Tim Burton experience (and that's not a pejorative). Doug Liman's “Go” fits well in the stride of independent filmmakers bursting forth, a pastiche of broken narrative ideas that were blooming throughout the decade. Mike Judge's “Office Space” captured corporate ennui perfectly. Pixar hit the gas with “Toy Story 2” as it would soar headlong into a new decade that would yield the animation studio's greatest work. I quite love the staggeringly human places David Lynch (of all people) reached with “The Straight Story.” Oliver Stone's “Any Given Sunday” proved Jamie Foxx could go and was just such an electrifying experience overall. And Martin Scorsese's “Bringing Out the Dead” seemed like the final toll of a stylistic bell that had been reverberating for 10 years by that time, an underrated modern classic.

What's bothersome, if anything, is how much the Academy snoozed on all of this. This is the year after Harvey Weinstein pulled a fast one on Steven Spielberg's “Saving Private Ryan” with a “Shakespeare in Love” Best Picture victory, so his outfit was in full swing with “The Cider House Rules.” And while that John Irving adaptation may have dabbled in not-so-safe content like abortion, it was still very much an in-their-wheelhouse play for voters that stuck out like a sore thumb amid all this bold creativity. The same might even be said of Frank Darabont's “The Green Mile.”

I maintain a love/hate relationship with “American Beauty,” captured in jaw-dropping strokes by cinematographer Conrad L. Hall, but not without its issues that would fill many more column inches. “The Insider” is a masterpiece, full stop, and M. Night Shyamalan's “The Sixth Sense” – a money-making monster – announced a promise that, we know now, would never be kept. But those were your Best Picture nominees. It didn't feel properly representative.

In any case, you look at all of these names and one thing stands out: Today's masters working alongside yesterday's. And that is what I truly take away from 1999. It was a time of change in the business and in the world, starkly reflected in the art of cinema. There has never been anything quite like it. For those reasons and more, 1999 is the greatest film year of all time.

Other pieces in this series:

1973 by Brian Formo

1974 by Daniel Fienberg

1977 by Louis Virtel

1980 by Richard Rushfield

1982 by Alan Sepinwall

1988 by Drew McWeeny

1995 by Jane Hu

1998 by Michael Oates Palmer

1999 by Kris Tapley

2001 by Chris Eggertsen

2012 by Zara Lisbon