Good movies entertain us. Great movies teach us how to live. In 1999 some movies were doing both. 

It's hard for filmmakers these days to have a goal beyond just getting stuff made and seen. At the same time, figuring out how to create good content and get it seen is sort like learning to drive. And ultimately what's the point of learning to drive if you don't know where to go? 

We're going to talk about the movies of 1999 because any filmmaker can learn to drive a car. We want filmmakers who take us somewhere interesting. Or cool. Or Unique. Or mind-blowing. 

Plus if you start with a story that might take audiences somewhere meaningful, you're definitely going to have an easier time getting it made and seen. 

What does this have to do with 1999 again?

1999 Movies Had it All

For whatever reason, 1999 produced a ton of new releases that took audiences to places they had never been before. Visually, emotionally, and philosophically. 

But you can't talk about movies in 1999 without talking about the elephant in the room...

Best Movies of 1999 Phantom Menace

Star Wars: Episode I - The Phantom Menace won the box office. Not just for the year, but for all time. It was probably the biggest single piece of movie news for the entire year. It drove the market, and in many ways, it was a look forward at where things were headed. 

We could go into what happened next in terms of fan culture, franchises, prequels and reboots, even visual effects. But those are conversations for another day. Suffice it to say that in 1999 George Lucas made cinematic waves that would change everything...and not for the first time. We'll come back to this later. 

1999 was a sort of a hinge moment for the industry though. Filmmakers from a prior era were still active (Robert Altman, Stanley Kubrick, Sidney Lumet, Martin Scorsese to name a few) while the names that would define the next era were just getting revved up (Paul Thomas Anderson, David Fincher, Alexander Payne, David O. Russell).

Best Movies of 1999 3 kingsDavid O. Russell's 'Three Kings' was one of many subversive yet mainstream movies in 1999

Scores of other great directors had major releases in theaters: Mike Judge, Milos Forman, Oliver Stone, Spike Lee, Sam Mendes, Sam Raimi, Wes Craven, David Lynch, Tim Burton, Ang Lee, Michael Mann, Rob Reiner, Lawrence Kasdan, Albert Brooks, M. Night Shyamalan, George Lucas, Trey Parker, Pedro Almodovar... the list goes on. 

Best Movies of 1999 electionAlexander Payne's 'Election' was another stand-out 1999 movie

The top 10 grossing movies from 1999: 

  • Star Wars: Episode I - The Phantom Menace
  • The Sixth Sense
  • Toy Story 2
  • The Matrix
  • Tarzan
  • The Mummy
  • Notting Hill
  • The World is Not Enough
  • American Beauty
  • Austin Powers: The Spy Who Shagged Me

Pretty diverse in terms of genre and style, with some true standouts. And that's not even the list of the movies that made 1999 so amazing. 

Before we get to that list... we have to talk about how we got to 1999. 

What defines the best year for movies?

Our lists here will focus largely American Film. There are countless great years of cinema that would also include international films and the truth is it becomes far more difficult to pick any year at that point. By narrowing it down to Hollywood, we had an easier time doing an 'apples to apples' comparison of years. 

But the bottom line is, there are so many great years for movies, it's really impossible to say with any confidence "X year was the best." 

What we can do instead is talk about some really critical years in terms of the slate of diverse and high-quality movies released that had a lasting impact on how movies were made. That'll be our criteria. 

Maybe along the way to 1999, we'll learn about the years that provided key turning points in the medium. 

One of the great stretches of international filmmaking was from the late 1940s into the early 1960s. American cinema's golden age, which we'll get to in a moment, inspired a rich take on the medium from around the world, that in turn would later re-ignite the stale and dying American studio system of the 1960s, giving the U.S. the late 1960s burst of independence that would usher in the second golden age of Hollywood in the 1970s. 

Best Movies of 1999 bonnie and clyde1967 was a lynchpin year, 'Bonnie and Clyde' kicked off a new era.

What is the Golden Age of Hollywood? It's not just an amorphous idea about the old studio system. It's a very specific era. 

1939 Movies and the Golden Age of Hollywood

People will often refer to various times as the Golden Age of Hollywood, but there is only one correct time. It's not 1999, it's not the early to mid-1970s either.

It's the 1930s.

This term was coined in reference to the 1930s because truly the form of the feature film with sync-sound was devised during that time. Many of the core elements of great cinema were established in silent filmmaking (and some might argue it's never truly been topped since). But with the intro of sound movies started to veer a little bit towards theater and suddenly the visual medium built on montage had to merge with another important performing art. 

When the pieces came together we got the first golden age of Hollywood and really the roots of all of cinema. 1939 was the capper of the decade of lessons learned and the list of important movies from that year is loaded with great directors and movies that endure to this day.

1939 has the MOST movies in the National Film Registry, which alone makes it pretty impressive. In some ways, there is no topping 1939 because it helped define the form. 

Best 1939 Movies

  • Gone with the Wind
  • Mr. Smith Goes to Washington
  • Ninotchka
  • Stagecoach
  • The Wizard of Oz
  • Gunga Din
  • Goodbye, Mr. Chips
  • Only Angles Have Wings

Any year that included Wizard of Oz and Gone With The Wind would have to be a biggie. Consider that both of them came from the studio MGM, which was the Disney of its time in terms of owning the rights to most valuable property, which back then was movie stars, not IP. 

Best Movies of 1939 Gone with the wind

While those two behemoths will take the lion's share of the credit for 1939 (get it, Lion's share? MGM? That's a pretty dated joke actually...) there are some other standouts that MIGHT have had even more impact on the way we make movies. 

John Ford, for example, burst into the center stage with the western Stagecoach. Stagecoach took the western genre from being b-movie one-reelers to being series cinema. That trend lasted for over half a century. How important is the western mythology to our culture? 

Pretty important. 

How important is John Ford and Stagecoach to western mythology making its way into the modern mainstream culture? 

Pretty important. Along with bringing back the western brought a brand new star. One that would also have a lasting impact. Born Marion Morrison, John Wayne aka the Duke became a screen icon because of John Ford and Stagecoach

When Was The Golden Age of Hollywood?John Ford's 'Stagecoach' helped turn the western genre into art

But Stagecoach's impact doesn't end there. Ford's gorgeous black and white photography and framing became a model for other filmmakers immediately. In fact, Orson Welles would famously say when discussing the visual inspiration for Citizen Kane, "John Ford, John Ford, and John Ford."

Only Angels Have Wings was a Howard Hawks adventure classic starring Cary Grant. Mr. Smith a morality play from Frank Capra starring Jimmy Stewart. Two more of Hollywood's biggest stars ever in two more of their defining roles from two more of the biggest directors. 

We could go on forever about how important those films and filmmakers are. But we need to get back to 1999. 

The Best Movies of 1976

Yeah, this is a big jump forward. There were many great years between 1939 and 1976, but 1976 is an important year in terms of what happened just before... and what would happen right after. 

The studio system that was built and perfected in the 1930s started to crumble by the mid-1960s and the influence of what was happening cinematically elsewhere in the world started to take hold on the younger creatives in the United States. The start of the new era of Easy Riders and Raging Bulls was around 1967, but it really reached its pinnacle in the mid-1970s and had its last gasp in 1976. And there is a very definite reason why.

  • Rocky
  • All the President's Men
  • Network
  • Marathon Man
  • Taxi Driver
  • Carrie
  • The Outlaw Josey Wales

Network is one of the most prescient movies of all time. It's hard to fathom just how ahead of it's time it was. In 1976 people thought it went "too far" when it depicted a news media that cared more about sensationalizing events and creating rambling mad-men for ratings than it did actual news. 

Network1976Howard Beale in Paddy Chayevsky's 'Network' predicted the future in more ways than anyone could have known


Flash forward to 2019 and ALL WE HAVE is sensationalized news with rambling mad-men. Network predicted everything, it was written by maybe the greatest screenwriter of all time, had an all-star cast, and was directed by one of the great directors. We won't try and do this work of genius service right here, we'll instead point you to Mad As Hell, an excellent companion piece to the movie and a must-read for anyone who loves cinema. 

1976 had Rocky as it's true headliner. Sylvester Stallone emerged from nowhere with his "one in a million" shot, becoming an instant icon and creating one of the most iconic characters. 

Best movies of 1976 Rocky'Rocky' was one in a million...

But he wasn't alone in new iconography. 1976 is the year Martin Scorsese truly made his presence felt. Though he'd burst onto the scene already with Mean Streets and Alice Doesn't Live Here Anymore, Taxi Driver was where the foundation of his cinematic legacy was cemented, along with the star he is most associated with, Robert De Niro.

Best movies of 1976 Taxi DriverAnother 1976 movie, another cinema icon

All The President's Men was another one of the most important movies of the era, about the recent watergate events, capturing the sudden shift in how Americans would relate to their Government and the media. 

Carrie would also come out, being a genre-defining moment for horror, and making Brian DePalma a bigger name. Clint Eastwood would direct one his first classics The Outlaw Josey Wales, of which Orson Welles would say "it belongs alongside the best entries in the western genre by Ford and Hawks" that's high praise from a man not easily given to such thing. 

Marathon Man pitted stars Dustin Hoffman and Lawrence Oliver against one another, as a kind of meeting of Hollywood's old style of acting vs. its new one. Which of course gave us the timeless quote attributed to Oliver after Hoffman "got into character" by running around the block however many times prior to a take. "My dear boy, why don't you just try acting?"

All in all, 1976 was a hinge year. It was a middle act. Filmmakers were getting bold, and being handed the budgets to do so. It featured anti-heroes and characters having breakdowns, coming into direct conflict with the society around them. 

From a visual standpoint, 1976 was flat-out punk rock. Shots from the movies on this list broke rules and created blueprints used to this day. Where Network set a new standard for dialogue and screen craft, Taxi Driver created a visual language a new generation of filmmakers would reference over and over... and over. 

What would the generation influenced by Travis Bickle do?

We'll get back to that... 

What happened next? 

In 1977 Star Wars was released and it ushered in a new era of film technology with special effects. It created a new business model for the industry when it opened to lines around the block, and multiple viewings from devoted fans. 

In the meantime, the filmmaker-first mentality began to hit a few snags. More than one celebrated young member of the first film school generation went way over budget and cratered a studio or production company. Heavens Gate and Michael Cimino are a popular example. 

It would take until Sundance and the "rise of the indie" for filmmakers to come first again but when they did it led us right into the year in question. 

The Best Year for Movies?

By 1999 the indie film explosion had happened. Steven Soderbergh and Quentin Tarantino led the way, via Sundance, for filmmakers with the indie spirit to get into the mainstream. Being a filmmaker was being an artist with a POV.

The result was a lot of stories that started to look inward. Many of these stories were about an existential crisis. It was as if the world wasn't providing enough conflict, so the characters had to have conflict with the blandness of what they'd become.

Best movies of 1999 Office spaceIn 1999 we all felt like we forgot to file those TPS reports.

They wondered about the meaning of their lives, the point of their existence if they were doing the best they could... if there was more to it than a cubicle.

The characters almost look out at us from within the screen and say "Why am I in this movie?" and the story struggles to answer the question. 

The Best Movies of 1999

In no particular order:

  • The Matrix
  • The Sixth Sense
  • American Beauty
  • Boys Don't Cry
  • Office Space
  • Being John Malkovich
  • Election
  • Eyes Wide Shut
  • Fight Club
  • The Insider
  • Blair Witch Project
  • Galaxy Quest
  • Three Kings
  • The Iron Giant
  • Toy Story 2

It was a very robust year in terms of movies that hit the theaters and had a generally positive reaction both at the time and in the two decades since. It's also a good list to consider today because the timing would have that many filmmakers and people working in the industry were likely influenced by quite a few of the movies on it. 

The list includes movies from almost every major genre. Blair Witch was a (sorry) game-changing entry into the horror genre. Whatever you think of it now, it changed the way movies are marketed and made. So did The Phantom Menace.

Best Movies of 1999 Blair Witch ProjectBelieve it or not, people actually believed one of the early 'found footage' movies was real.

The word "prequel" hardly existed prior to The Phantom Menace. Sequel, Prequel, Reboot, Rebootquel... this is the world we live in today. 

Identity and point of view was the through-line to many of the best movies of 1999. Characters struggling with who they were, and the reality they perceived or were stuck in. This applies to The Matrix just as much as it applies to Boys Don't Cry

Best Movies of 1999 The MatrixWhat was it about 1999 and cubicles?

The Matrix and Office Space were both really about the same exact topic. Office Space uses the device of a hypnotist to help its protagonist find his true self. The Matrix uses the device of a sci-fi hellscape and a battle for freedom against machines. American Beauty was also about a character who's comfortable life and identity was really a sham barely covering his misery. 

Characters in 1999 were 'breaking out' of the mold they were stuck in. The antagonist they faced was a restrictive society. Being John Malkovich is literally about inhabiting another human to experience life more completely. It's also a Swiss watch of a screenplay that despite being unique and original in the most extreme sense, checks off so many of the boxes. 

Best Movies of 1999 Being John MalkovichOf all the unique and amazing movies of 1999, could 'Being John Malkovich' be the weirdest (best)?

The movies of 1999 were formally well constructed, but deeply original and unique. Election turned a story about a high school election into a darkly comic parable. It mashed genres and upended expectations. Galaxy Quest is often called "the best Star Trek movie" because it took a fictionalized reality behind the famous IP and blended it with the fantasy to tell a story about, what else in 1999, people who felt inauthentic (it's not a Star Trek movie).

What can we learn from the best movies of 1999 as a whole?

That point of view matters as much as craft. These movies of 1999 were all exquisitely crafted by some of the greatest filmmakers who ever lived. But they had something at their core driving the choices. Fight Club was trying to say something, and in the process, it managed to speak to people. The Matrix was far more than groundbreaking sci-fi action. It was an entire philosophy class and a nuanced world view. 

Best Movies of 1999 Fight Club#1999 #cubiclelife

When creatives can align the tools of the trade with ideas that matter to them, the results are transcendent. In 1999 it worked out that a lot of filmmakers were given the leeway to do just that. 

The good news is it's a lot easier to put a story on a screen in front of audiences than it was in 1999. 

Back then there was no YouTube. No Facebook. No digital revolution. All the movies on this list? They were shot on celluloid. 

Filmmaking has since been democratized. We talk a lot about how to shoot, but we can look back to 1999 and think about why we're shooting in the first place. What do we have to say? 

If we start there we may just find that people want to listen.