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The 21 Best Films Of The 21st Century So Far

There’s no better way to see what happened, what could have been, or perhaps what should have been than a look at The Oscars year by year.

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With the year 2021 over, all the eligible films for Hollywood’s annual awards have now come out, and the top contenders are up for discussion. It’s also the end of the 21st year of the 21st century, a good opportunity to look back, as Hollywood is well into its second century now.

There’s no better way to see what happened, what could have been, or perhaps what should have been than a simple look at The Academy Award for Best Picture year by year. Mistakes were clearly made, awards intentionally politicized, and cultural identity revised relentlessly.

This could be a much bigger issue to discuss and deliberate, but for an end-of-year list we’ll simply mention what won versus what was in the running. In doing so, we’ll see who we were just a few years back and who we are today as the 21st century unfolds.

2000: ‘Gladiator’

In 1999, “American Beauty” won the Best Picture Oscar, perhaps denoting the end of the American Century. That’s because the 21st century began with “Gladiator,” Ridley Scott’s trademark decadence and emptiness, telling the story of the Roman Empire’s imminent demise. “Crouching Tiger, Hidden Dragon” should have won the Oscar, if only for its revolutionary effects that laid the foundation for Marvel and every single sci-fi or action movie since.

2001: ‘A Beautiful Mind’

Russell Crowe carried “A Beautiful Mind” across the finish line, so to speak, even though it ended up unintentionally dismayed, empty, even vapid in its third act. “The Lord of the Rings: The Fellowship of the Ring” was the best film that year, but The Academy knew it was a triptych, so they’d be rewarding Peter Jackson for his epic undertaking in a couple of years.

2002: ‘Chicago’

As a return to an age-old cabaret vibe filled with talent and energy, “Chicago” took the prize. But realistically, it didn’t have much competition. “Gangs of New York” became a Scorsese knock-knock joke, and while “The Pianist” was a clearly better “film,” Adrien Brody’s performance wasn’t enough to let The Academy forget it was directed by Roman Polanski, one of the first world-class directors whose past was beginning to get too strange, difficult, and unacceptable. Little did they know what cancel culture would ultimately become.

2003: ‘The Lord of the Rings: The Return of the King’

When the final installment of Peter Jackson’s epic adaptation of J. R. R. Tolkien’s “The Lord of The Rings” finally came out, the Best Picture Oscar statue was already being engraved. While “The Lord of the Rings: The Return of the King” was not as astounding or inspiring as the original or even the sequel, the cinematic storytelling masterpiece deserved the Academy Award across the board. In any other year, “Lost in Translation” would have won because of its tone, tenor, and Scarlett Johansson’s debut pitted against Bill Murray’s apex.

2004: ‘Million Dollar Baby’

Ever so often, even Hollywood is able to view, recognize, and award the right film for the right reasons. With “Million Dollar Baby,” the story, the direction, the performances, and especially the timing are undeniable.

Not only is it Eastwood’s best performance since “Unforgiven,” but Hilary Swank deservedly received Best Actress, Morgan Freeman earned Best Supporting Actor, and Eastwood won Best Director. An authentic, heartfelt story of redemption through unforgivable means, “Million Dollar Baby” is not only an exceptional film but a necessary discussion of morality and meaning.

2005: ‘Crash’

From the highest highs to the lowest lows, the very next year after “Million Dollar Baby,” “Crash” was awarded Best Picture. Almost immediately Hollywood realizes not only that it’s a downright terrible film, but also that its egregious conversation about racism, inequality, violence, and humanity’s flaws is at times laughable.

The faint smell of revisionist policies affected other nominees as well, with “Brokeback Mountain” presenting “rugged homophobia” and “Munich” “re-evaluating” Holocaust revenge strategies. This Best Picture failure did not bode well for The Academy’s future.

2006: ‘The Departed’

Every few years The Academy realizes it’s time to honor a legend, so “The Departed” became that moment for Martin Scorsese. While it remains at least arguable that he’d earned the Best Director Oscar, the film by no means deserved Best Picture.

Despite an A-list cast, the story itself proved untenable and thin as ice, with a noticeably misguided performance by Jack Nicholson that probably convinced him it was time to retire. If not for the Scorcese variable, all signs pointed to “Little Miss Sunshine” for refreshing levity and originality.

2007: ‘No Country for Old Men’

The Academy Awards are notorious for crests and valleys, for accomplishments that define generations and moments that everyone wishes they could erase. After a couple of years lost in the woods, two films emerged that defined cinema’s inherent prophetic profundity.

“No Country for Old Men” is quite simply a masterpiece. The Coen Brothers are at their very best, directing three of the finest lead performances in recent memory, with a story that’s just as auspicious as its naturalism and articulate spiritual analysis. Javier Bardem won Best Actor, and to this day his portrayal of Anton Chigurh is deemed the most realistic depiction of sociopathology ever filmed.

If not enough, an equal contender was “There Will Be Blood,” a frontier character epic from Paul Thomas Anderson with a mesmerizing, unforgettable performance by one of the finest actors in cinema history, Daniel Day-Lewis.

2008: ‘Slumdog Millionaire’

A classic example of time’s collision with timing, “Slumdog Millionaire” winning Best Picture is more of a story about Western revisionism merging with a global game show craze caused by “Who Wants to Be a Millionaire.” While Dev Patel’s performance is acceptable and the story is enchanting and exhilarating, “Slumdog Millionaire” gets flimsier and less significant with every passing year. But perhaps it won the Oscar legitimately when its only competition was the laughable “The Curious Case of Benjamin Button” or the overtly political “Milk.”

2009: ‘The Hurt Locker’

“The Hurt Locker” being awarded Best Picture is yet another example of timing, but this instance proves strategy and intentionality. A film critical of military expansion and warrior mentality in the 21st century directed by a politically charged woman that manages to indirectly criticize an American president who started an illegitimate war? Yes, please. Thank you.

Among unique, original, favorable, or even forward-thinking contenders like “Inglourious Basterds,” “A Serious Man,” or “District 9” — and the first year The Academy named 10 nominees instead of five — “The Hurt Locker” proved two things: Jeremy Renner is a capable frontman and films can and should (and will) express political propaganda.

2010: ‘The King’s Speech’

Again, a reset. A simple straightforward Best Picture to a deserving film; not so much a masterpiece as a relevant historical glance at a unique character and the moment that defined Great Britain approaching World War II.

Amid devastatingly realistic performances in “The Fighter” or the sweeping tech masterclass “Inception” created, “The King’s Speech” remained grounded and dignified, and actually pulled pivotal elements from both. Colin Firth as King George VI and Geoffrey Rush as his linguist specialist preparing him for a wartime speech amid an expansive depiction of England approaching its historic role in saving Europe and the world made a clear, decisive, and necessary statement.

2011: ‘The Artist’

Although superficial in the sense there wasn’t much beyond visual excellence and classic flair, “The Artist” manipulated old-fashioned nostalgia quite effectively. In that sense, it deserved the Best Picture Oscar, but with a rather weak list of nominees, even Woody Allen’s “Midnight in Paris” or “Moneyball,” a downplayed American pastime analysis, were arguably better features. Nonetheless, “The Artist” proved yet again that nostalgia — the intentional reference to the way the past makes us feel — is all it takes sometimes.

2012: ‘Argo’

In hindsight, the year “Argo” won Best Picture foreshadowed three dominant trends that have continued in Hollywood ever since. First, politics is undeniably preeminent. Any film that provides an implicit or even explicit leftist perspective will be hailed just for its intentionality. Second, identity overshadows performance. It’s more important that the right actor “acts” than the right performance “performs.”

Third, overall quality is in decline for a multitude of reasons: production value, international competition, global perspective, and social media influence. In other words, “Argo” may have been competent, but was far from momentous, let alone meaningful.

2013: ’12 Years a Slave’

The very next year a candid, violent, and damning portrayal of American slavery won Best Picture. Fittingly, to this day it’s difficult to assess the long-term effects and implications of “12 Years a Slave.” The performances were intimate, dignified, even exceptional — especially Lupita Nyong’o, who won Best Supporting Actress — and the quality of the filmmaking both in terms of story and adaptation proved articulate and authentic.

Yet what we’re told to remember about the actual film is less its narrative, and more its unprecedented production “characteristics.” Yes, “12 Years a Slave” won Best Picture with the first black producer and the first black director, but is that what the film was meant to signify? In other words, the separation of the art and the artist became muddled. Irreversibly and permanently.

2014: ‘Birdman (or The Unexpected Virtue of Ignorance)’

Identity and globalization moved forward unabated the following year when “Birdman (or The Unexpected Virtue of Ignorance)” swept the production Oscars and awarded Alejandro G. Iñárritu Best Director. As a dark comedy-drama with a stellar “comeback” performance from Michael Keaton, “Birdman” proved to be the legitimate favorite of the year. But there were a few others nipping at its heels including “The Grand Budapest Hotel,” “Boyhood,” and even “Whiplash.” A strong year on the storytelling narrative level, Iñárritu’s credentials, talent, and international appeal sealed the deal.

2015: ‘Spotlight’

With a biographical drama like “Spotlight,” The Academy had another chance to prove the Best Picture award wasn’t just honoring a formidable film, but also making a necessary and time-sensitive statement — perhaps not overtly political, but clearly against an acceptable, politically incorrect villain: the Catholic Church. A story about the Boston Globe’s investigative journalists responding to widespread and systemic child sex abuse not only won a Pulitzer in 2003 but an Oscar a decade later. And even though the contenders were limited, “The Revenant” was actually better in terms of performance and profundity. It’s just that the message counted more than the metaphor that year.

2016: ‘Moonlight’

Not unlike the 2016 election, the Best Picture Oscar came down to two very different, very disparaging, and very flawed versions of what the best film of the year should be. On one hand, you had an articulate and demanding coming-of-age drama suffering from an unnecessarily flawed and featureless third act, and on the other you had a musical comedy-drama love story about Los Angeles, The Industry, and hopes and dreams becoming our lives and loves. While it was truly a coin toss, “La La Land” was announced the winner until the recipient declared a mistake on stage at The Academy Awards. So “Moonlight” won “by mistake.” Or did it?

2017: ‘The Shape of Water’

When a romantic fantasy like “The Shape of Water” beats Dunkirk to win the Best Picture Oscar, there’s more going on than just the quality of any given film. And in this case, it was honoring an international director like Guillermo del Toro. Ironically, his past films had proved much more profound and inquisitive than “The Shape of Water,” but after the Best Picture “incident” the previous year, The Academy decided to lean on devotion instead of derangement.

2018: ‘Green Book’

Despite its numerous accolades, perhaps the reason “Green Book” won Best Picture is a good example of the-simplest-answer-is-probably-the-right-one: it’s easy. “Green Book” is an American autobiography against a racist past in the South victimizing jazz performers that pretty much everyone can agree is “correct,” “necessary,” and “exactly what happened.”

Is it an exceptional film? Not really. Is it safe? Yup. Is it anywhere near “A Star Is Born” in terms of performance quality, engaging narrative, or a sweeping soundtrack? (And keep in mind, “A Star Is Born” is a remake that’s essentially the movie version of vanilla ice cream.) Definitely not.

2019: ‘Parasite’

As globalism takes hold, Hollywood either adapts or dries on the vine. So in a strange way, “Parasite” threw it a lifeline by legitimately presenting an impressive cast and story entirely produced in South Korea.

The headlines spoke volumes when they claimed “Parasite” was the first foreign film to win Best Picture. Again, it’s historic, it’s well-earned and fitting, and it was absolutely necessary for Hollywood to evolve and survive. All in all, either “Joker” or “Once Upon a Time in Hollywood” were better films in terms of quality, performance, and intentionality, but Joaquin Phoenix won Best Actor and Alfonso Cuarón, director of “Roma,” received Best Director. Fair’s fair.

2020: ‘Nomadland’

The year of COVID-19 shut things down entirely and almost made The Academy Awards senseless or even inappropriate. So it’s quite fitting that “Nomadland” won Best Picture, either because it became a convenient way to honor a foreign female director and feminist female lead or because every other film was essentially non-existent.

All jokes aside, given the pandemic, perhaps the slice-of-life moments and vignettes depicting like-minded Americans were exactly what The Academy wanted to honor? Probably not. But sometimes hope is all we have.

2021: ?

So here we are. What 2021 film will win the next Academy Award for Best Picture? It depends on the X-factor currently dominating. If it’s legitimate production quality, it could be “Dune.” Performance valor and resonance would indicate “The Tragedy of Macbeth” or even “Pig.” (Believe it or not.)

The Industry counting its blessings that movie-going still exists might mean “Spider-Man: No Way Home” could surprise everyone. If it’s early Oscar buzz, “The Power of the Dog” is currently the frontrunner. And if it’s time to honor a director’s career and influence, perhaps Paul Thomas Anderson’s “Licorice Pizza” will be the surprise that won’t age well. So all that’s left to say is: We shall see.