Every Film That Should Have Won Best Picture (But Didn’t) Since 1998

Brightcast Media

We have witnessed countless film classics over the years, with many being recognized with Academy Award nominations. However, we are going to play devil’s advocate here, noting which film each year should have won Best Picture, but ultimately did not.

*Please note that the year listed is when the Academy Awards took place, NOT the year the film was released

1998: L.A. Confidential

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Nominees:

• Titanic (actual winner)
• As Good As It Gets
• Good Will Hunting
• The Full Monty
• L.A. Confidential

Titanic was certainly the “most” picture of 1997. But the best? That honor should have gone to Curtis Hanson’s brutal and brainy crime drama L.A. Confidential. The film is chockablock with actors delivering A+ performances. Kim Basinger doesn’t get the same acclaim as her male counterparts (and her character is a bit of a stock noir trope), but she is electric in this film. The same can be said of Danny DeVito — who appears to be having the time of his life as Sid Hudgens, the sleazy tabloid publisher.

The plot is fast-moving and complex, and rewards an audience that’s game for the ride and willing to give it the proper attention. Sure, it isn’t an epic in the same way that Titanic is, but the gritty, hard-boiled crime film is proper modern noir — and undoubtedly one of the best films of the ’90’s.

1999: Saving Private Ryan

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Nominees:

• Shakespeare In Love (actual winner)
• Elizabeth
• Life is Beautiful
• Saving Private Ryan
• The Thin Red Line

In retrospect, it’s shocking Saving Private Ryan didn’t grab the Oscar in 1998. Though admittedly, we didn’t know just how great of an impact the film would ultimately have. Spielberg and his cinematographer Janusz Kaminski’s hand-held, ground-level camera work (with a desaturated color palette) has since been almost universally adopted as the visual language of war.

While the Omaha Beach scene is the most memorable, Spielberg follows that dizzying opening fifteen minutes with a powerful, honest story that manages to show the realities of war without glorifying violence. Perhaps the best World War II film ever made, and certainly the best picture of 1998.

2000: The Sixth Sense

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Nominees:

• American Beauty (actual winner)
• The Cider House Rules
• The Green Mile
• The Insider
• The Sixth Sense

It’s easy for modern audiences to downplay the incredible sleight of hand performed by M. Night Shyamalan in The Sixth Sense akin to the same way we might mock the beauty of a plastic bag caught in the wind. When things become part of the zeitgeist, we tend to take them for granted.

Unless you go in completely cold, it’s hard to grasp how hard the final moments of The Sixth Sense. However, don’t let that fool you into thinking the film is a one-trick pony. Even if you know the twist, it’s still a haunting, beautiful ghost story buttressed by one of the best performances by a child actor put on film. It’s also a quiet, understated turn from Bruce Willis. What an incredible freshman offering from director M. Night Shyamalan that would set the standard for the rest of his career, for better or worse.

2001: Crouching Tiger Hidden Dragon

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Nominees:

• Gladiator (actual winner)
• Chocolat
• Crouching Tiger Hidden Dragon
• Erin Brockovich
• Traffic

It feels reductive to simply state that Crouching Tiger Hidden Dragon is an incredible martial arts film. It absolutely is, and the action dreamed up by famed choreographer Yuen Wo-Ping is unlike anything western audiences had seen when the movie premiered in 2000. Yet, what makes the film transcend its genre (and borders, as it was an unexpected hit in the United States, a typically subtitle-averse audience) is the depth and emotion of its story. Love, duty, the pressure of societal norms…while the action takes us flying across rooftops or into the dizzying heights of swaying trees, the drama always remains grounded.

2002: The Lord of the Rings: The Fellowship of the Ring

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Nominees:

• A Beautiful Mind (actual winner)
• Gosford Park
• In the Bedroom
• The Lord of the Rings: The Fellowship of the Ring
• Moulin Rouge!

Right sentiment, wrong movie.

When the third and final Lord of the Rings movie won best picture it was, from all appearances, an award for the trilogy as a whole. Shot simultaneously from October of 1999 to December of 2000, everyone involved deserved recognition for the achievement in filmmaking that it was. But the Fellowship of the Ring, not The Return of the King, was the best of the three. It really should have been given the honors. Fellowship had the formidable task of introducing the world of Middle Earth to a general audience — the foundational lore, the larger themes and the nine central companions. Had it failed, so would the rest of the trilogy.  Fellowship was a success on every level, and manages to tell the most satisfying, self-contained story of the three.

Also, it’s the one with Sean Bean.

2003: Gangs of New York

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Nominees: 

• Chicago (actual winner)
• Gangs of New York
• The Hours
• The Lord of the Rings: The Two Towers
• The Pianist

We should be talking about Daniel Day-Lewis’ performance as Bill “the Butcher” Cutting with the same reverence and hushed tones reserved for his turns as Daniel Plainview or Abraham Lincoln. About halfway through the film Bill, draped in the American flag, thrones himself next to a half-awake Leonardo DiCaprio and delivers a hypnotic monologue about fear and the last honorable man in the New World. It is worth the price of admission alone.

Gangs of New York is not Scorcese’s greatest work, and it is at times uneven or unsure of what it is trying to say. And yes, Cameron Diaz’s Irish accent is…unfortunate. But the good significantly outweighs the (arguably) bad. An excellent ensemble cast, stunning production design, and a singular performance elevates this above any of the other nominees this year.

2004: Master and Commander: The Far Side of the World

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Nominees: 

• The Lord of the Rings: The Return of the King (actual winner)
• Lost in Translation
• Master and Commander: The Far Side of the World
• Mystic River
• Seabiscuit

Since we’ve already given the Lord of the Rings Oscar to Fellowship back in 2001, the Academy is no longer obligated to give the trophy to Return of the King. The Oscar now goes to Master and Commander: The Far Side of the World, a film that is as great as its title is awful. The film feels at times episodic, with director Peter Weir deftly blending quiet scenes of character– along with the wonders of nature with bombastic Napoleonic-era naval action.

Ultimately, it’s the relationship of the Captain and the ship’s doctor — Russell Crowe and Paul Bettany respectively — that ties the film together. The actors have a chemistry giving their friendship an authenticity that recalls the best dyad’s in fiction (Star Trek’s Kirk and Spock springs to mind). Fun, thoughtful, tense, exhilarating. Terribly underrated and worth another look.

2005: Sideways

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Nominees: 

• Million Dollar Baby (actual winner)
• The Aviator
• Finding Neverland
• Ray
• Sideways

The sad guy wine movie? Really?  Yes, the sad guy wine movie. Really.

You could certainly make the argument that the world has given enough honors to movies about middle-aged white men dealing with the unfulfilled expectations of their lives. That’s basically half of 1990’s independent cinema. However, judged against the other nominees, it’s still the best picture of the bunch. The script is clever, observant, and quite funny. Thomas Haden Church is delightful as an aging himbo, and Paul Giamatti does some of his best work here showing us a flawed, pained man hiding behind his pretentions. His character’s meltdown at a winery where he demands a “full pour” is an all-timer.

The film was also responsible for a massive drop in Merlot sales upon its release. Not many other movies can make such a claim. I don’t think Million Dollar Baby had any effect on the sales of… whatever it is people drink while boxing.

2006: Brokeback Mountain

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Nominees: 

• Crash (actual winner)
• Brokeback Mountain
• Capote
• Good Night, And Good Luck
• Munich

Here’s something we can likely all agree on: Crash should not have won best picture. My guess is that the other, stronger nominees all split the vote — and Paul Haggis’ uneven melodrama took the statue. The actual best picture in 2005, in my opinion, was Ang Lee’s Brokeback Mountain.

Beautiful and heart-wrenching, the film combines the visual language of the western with a story of forbidden love. It was made more tragic because what keeps these lovers apart is internalized. Fear and shame borne from a toxic culture, and how that can weigh on and ultimately shatter people’s lives. The entire cast is unsurprisingly fantastic. Heath Ledger completely disappears into the role. I would argue that Ennis del Mar is his greatest performance. Capote, Munch and Good Night, And Good Luck are all fine films, but Brokeback Mountain is a step above.

2007: Letters From Iwo Jima

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Nominees:

• The Departed (actual winner)
• Babel
• Letters From Iwo Jima
• Little Miss Sunshine
• The Queen

While the Oscar will officially go to Letters from Iwo Jima, it will have to be shared with the film that serves as its companion piece: Flags of Our Fathers. Both films depict the Battle of Iwo Jima that took place in February and March of 1945, with the former showing the conflict from the perspective of the Japanese (and the latter the Americans). Both films individually are astonishing (with Letters From Iwo Jima the superior of the two) but as a pair they offer unique insights into how we view good and evil during war — that those lauded as heroes depend entirely on which side of the battlefield we’re viewing.

2008: Michael Clayton

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Nominees:

• No Country For Old Men (actual winner)
• Atonement
• Juno
• Michael Clayton
• There Will Be Blood

Michael Clayton is a brooding character study wearing the clothes of a tightly wound legal thriller. It is also a picture with a specific kind of brilliance that’s hard to pin down. What elevates this film above others in the genre? The script is phenomenal, of course. Tilda Swinton, Tom Wilkinson and George Clooney are at the top of their game. Beautifully photographed, well edited. Everything is working here.

But it all adds up to more than that. There’s something about Michael Clayton that feels “Important.” An incredible achievement for a first-time director, even if Tony Gilroy was already a veteran screenwriter. Michael Clayton seems to have been a bit forgotten in the fifteen or so years since its release. That’s a shame, because it’s one of the finest films of the 2000s.

2009: Milk

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Nominees:

• Slumdog Millionaire (actual winner)
• The Curious Case of Benjamin Button
• Frost/Nixon
• Milk
• The Reader

Arguably the weakest field of best picture nominees in the history of the Academy Awards. The Reader is middling Oscar bait only remarkable for Kate Winslet’s performance. Benjamin Button gets bogged down by its own premise. Frost/Nixon has two great performances, but never quite shakes the feeling we’re watching a play and not a movie.

That leaves us to choose either Slumdog Millionaire or Milk. Slumdog is an exciting fable, but it has to be Milk. Well written, well directed, great cast — there’s nothing here to criticize. One of the best biopics of the 2000’s.

2010: A Serious Man

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Nominees: 

• The Hurt Locker (actual winner)
• Avatar
• The Blind Side
• District 9
• An Education
• Inglourious Basterds
• Precious: Based on the Novel Push by Sapphire
• A Serious Man
• Up
• Up In The Air

A Serious Man is a peculiar film. There’s an unease throughout the entire 100 minute run-time as we’re made to feel as uncomfortable and put-upon as Larry Gopnik, our protagonist. As he confronts increasingly hostile life changes and social situations, Larry reaches out to the people around him for answers — answers that come back at him and the audience perpendicular to his questions.

Just as Larry repeatedly asks “what’s going on?” so too do we as the movie unfolds. God doesn’t seem to feel obligated to give Larry easy answers, nor do the Coens to their audience. Even the prologue of the film — set in a Polish shtetl in the 1800’s — appears to have a tenuous connection to the rest of the film. More questions. We’re even denied a resolution entirely, as the credits start to roll when most films would enter their third act. If that sounds frustrating, it’s because it is. But it’s also provocative, witty, and profound. I can’t stop thinking about this film, the best picture of 2009.

2011: The Social Network

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Nominees:

• The King’s Speech (actual winner)
• 127 Hours
• Black Swan
• The Fighter
• Inception
• The Kids Are All Right
• The Social Network
• Toy Story 3
• True Grit
• Winter’s Bone

The Social Network was not just the best movie of 2010, but arguably the best movie of the 2010’s. The script alone is an achievement. Aaron Sorkin managed to craft a tight, propulsive narrative around a bunch of young, unlikeable people creating a website. The dialogue is fast and there’s a lot of it (thankfully it’s all excellent). David Fincher’s direction is equally sharp and kinetic. The film sweeps you up in its narrative, as you barrel from scene to scene. Like Facebook itself, the film at times feels like a runaway train. Thankfully, Trent Reznor’s beautiful, melancholic score always shows up exactly when needed to give scenes the emotional weight that pace might not have allowed for.

There’s an additional element of dread added to The Social Network when you watch it today, knowing what Facebook will become. You sit, helplessly watching small, petty men quibble over position on the masthead or dilution of shares, with no thought or care as to the effects of the monster they’ve created.

2012: The Tree of Life

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Nominees: 

• The Artist (actual winner)
• The Descendants
• Extremely Loud and Incredibly Close
• The Help
• Hugo
• Midnight in Paris
• Moneyball
• The Tree of Life
• Warhorse

The Tree of Life is a singular work. I would argue it has more in common with a poem than it does a motion picture. It is ambitious, challenging, and beautiful. Despite director Terrence Malick’s esoteric style, the story is fairly straightforward. A disillusioned man sifts through the memories of a difficult childhood, searching for answers or solace. We are presented with the creation of the universe, visions of the afterlife and the eventual destruction of Earth.

The images and moments wash over us like a dream, some more fleeting than others. But what does it all mean? That’s not for me to say. There are countless articles and essays trying to claim that the film is expressly about this or that. Personally, I think it’s missing the point. The Tree of Life leaves you to interpret it however you’d like. It’s certainly not for everyone, and I don’t blame you if you don’t like it. Still, it deserved to win Best Picture.

2013: Lincoln

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Nominees:

• Argo (actual winner)
• Amour
• Beasts of the Southern Wild
• Django Unchained
• Les Misérables
• Life of Pi
• Lincoln
• Silver Linings Playbook
• Zero Dark Thirty

What a delight it was buying a ticket to Lincoln, expecting a stuffy and “important” biopic. Instead, we were treated to a well-crafted and at times surprisingly fun political thriller. The cast is of course stellar.

Daniel Day-Lewis presents us with a now definitive take on Abraham Lincoln. There’s an authenticity to the performance. It makes us wonder whether Day-Lewis had managed to somehow actually meet the man and study him. Despite a few saccharine moments, Spielberg’s take on “Team of Rivals” is one of his best movies to date.

2014: American Hustle

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Nominees: 

• 12 Years a Slave (actual winner)
• American Hustle
• The Wolf of Wall Street
• Captain Phillips
• Dallas Buyers Club
• Gravity
• Her
• Nebraska
• Philomena

American Hustle is a mess. There’s a lot of improvisation going on here, both in front of and behind the camera. Loosely (and I mean loosely) based on the Abscam FBI sting, David O. Russell gives us his best attempt at a Martin Scorcese impression, borrowing liberally from films like Casino and Goodfellas. Half the cast is wearing a ridiculous wig. The other half has giant hoop earrings and a ridiculous perm. Pure chaos. I loved every minute of it.

You can’t look away from American Hustle. Every performance is vibrant. Extra kudos to Jennifer Lawrence and Bradley Cooper, who manage to steal scenes occupied by Amy Adams and Christian Bale. This is one of the most fun and funniest films on this list — a joy to watch. Ten out of ten.

2015: Whiplash

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Nominees: 

• Birdman or (The Unexpected Virtue of Ignorance) (actual winner)
• American Sniper
• Boyhood
• The Grand Budapest Hotel
• The Imitation Game
• Selma
• The Theory of Everything
• Whiplash

There’s as much jazz in the editing and direction of Whiplash as there is in the songs played by the film’s Shaffer Conservatory Studio Band. Director Damien Chazelle brings us into the rehearsals and performances. We’re talking extreme closeups of crashing cymbals, drops of blood, the snap-slide of a trombone — and even beads of sweat landing on a snare drum. It expertly tunes the audience into the precision and detail demanded of these young musicians.

The story itself is fairly boilerplate, elevated by the two leads. J.K. Simmons’ monster of a conductor throws insults and cymbals at his students. Miles Teller impresses as a young, obsessive musician who enters into a battle of wills with his abusive instructor. It’s the final scene, though, that earns this movie it’s Oscar, when the struggle between mentor and mentee crescendos to one incredible, exhausting final moment.

2016: Mad Max: Fury Road

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Nominees:

• Spotlight (actual winner)
• The Big Short
• Bridge of Spies
• Brooklyn
• Mad Max: Fury Road
• The Martian
• The Revenant
• Room

It may not be as “important” as a Spotlight or a Room, but Mad Max: Fury Road is one of the most exciting, bombastic action films of the last decade. An instant classic in every sense of the word. Told almost exclusively via visuals, each frame is bursting at the seams with color and detail. The movie is ostensibly a single continuous chase scene with only a few fleeting moments to allow you to catch your breath — as if George Miller completed the final action set piece of The Road Warrior and then spent the next 30 plus years figuring out how to blow it out to feature length with every bizarre, deranged thought that popped into his head. This is a roller coaster masquerading as a motion picture. What a ride.

2017: Arrival

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Nominee: 

• Moonlight (actual winner)
• Arrival
• Hacksaw Ridge
• Fences
• Hell or High Water
• Hidden Figures
• La La Land
• Lion
• Manchester By The Sea

Before I lay out my argument for the greatness of Arrival, I would like to just say that I think the Academy actually got it right this year. Of the nominees, Moonlight was the best picture. But for the sake of the article, let’s enter into an alternate universe where Moonlight wasn’t nominated. Also, if we gave the award to Arrival instead of Moonlight, it might have saved Warren Beatty, Faye Dunaway and the producers of La La Land a significant amount of embarrassment on Oscar Night.

Arrival is the kind of intellectual science fiction that we need more of. It’s less concerned with creature design or ‘splosions than with thoughts on the nature of communication and language. That’s not to say there aren’t amazing creatures (the heptods are among the most unique I’ve seen in a film), and there’s at least one explosion. But none of that ever outshines Amy Adams’ commanding performance. It’s a crime she wasn’t nominated. The drama plays out beautifully and with an unexpected turn that re-contextualizes everything. Truly an incredible piece of filmmaking.

2018: Lady Bird

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Nominees:

• The Shape of Water (actual winner)
• Call Me By Your Name
• Darkest Hour
• Dunkirk
• Get Out
• Lady Bird
• Phantom Thread
• The Post
• Three Billboards Outside Ebbing, Missouri

Writer-Director Greta Gerwig has taken something very familiar and made it brand-new again. This is a high school coming-of-age story with all the common tropes — the school musical, prom night, losing your virginity, parental strife. Yet, she still manages to make the story totally and completely fresh. Lady Bird is simultaneously extremely specific to a time and place…yet completely universal. We may have never been a seventeen year old girl living in Sacramento between the fall of 2002 and fall of 2003, but the feelings and experiences here are universal.

Its charm comes from how honest and unflinching it is. Each scene is so natural and real that at times it’s more like eavesdropping than watching a movie. The writing and direction is superb, but much of this is owed to the phenomenal cast. Saoirse Ronan and Tracy Letts are phenomenal. Laurie Metcalf is perfection. A stunning performance. She deserves ALL of the awards. All this in less than 90 minutes. Lady Bird is a triumph.

2019: The Favourite

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Nominees:

• Green Book (actual winner)
• Black Panther
• BlacKkKlansmen
• Bohemian Rhapsody
• The Favourite
• Roma
• A Star is Born
• Vice

Olivia Colman is the jewel in this film’s proverbial crown (pardon the pun). There’s a physicality to her portrayal of Queen Anne that is nothing short of stunning. She embodies the queen like three children stacked on one another in a trench coat, performing the duties of a monarch.  It is a delight to see her spin about as Emma Stone and Rachel Weisz’s characters vie for her favor (or is it favour?).

This pitch black comedy is as fun to watch as it is beautiful in its grotesqueness. The production design and wardrobe is stunning, and everything is exaggerated by Director Yorgos Lanthimos’ love for wide angle lenses. This film is also a reminder that, like in The Great, Nicholas Hoult was born to wear silly wigs and silk pants.

2020: Once Upon a Time in Hollywood

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Nominees: 

• Parasite (actual winner)
• Ford v Ferrari
• The Irishman
• Jojo Rabbit
• Joker
• Little Women
• Marriage Story
• 1917
• Once Upon a Time in Hollywood

To borrow a term coined by Quentin Tarantino himself, Once Upon a Time in Hollywood is a phenomenal “hangout film.” There’s a plot, sure — tension around Rick Dalton’s career prospects, run-ins with cults, remembered backlot brawls — but the movie is never in any kind of rush to get to any of it. The ending is shocking and explosive, yes, though that feels like an exclamation point at the end of a miles-long run-on sentence.

The greatness of this movie comes from the characters. The small moments. The vibe. This idealized, glorified version of 1960’s Hollywood with people like Rick Dalton and Cliff Booth is a great place to hang out for 2 hours and 41 minutes. That’s enough to win best picture.

2021: Judas and the Black Messiah

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Nominees: 

• Nomadland (actual winner)
• Judas and the Black Messiah
• Mank
• Minari
• Promising Young Woman
• Sound of Metal
• Trial of the Chicago 7

Nomadland was celebrated for what it said about America, a post-Great Recession period piece with themes that are still relevant today. In light of what was going on in the summer of 2020, I would argue that Judas and the Black Messiah did the same. Fred Hampton’s story is one that should be more broadly known.

This film is anchored by its two leads. Lakeith Stanfield is brilliant as the tortured William O’Neal. The anxiety and unease that simmers beneath the outward façade is a perfect contrast to Daniel Kaluuya’s steadfast portrayal of Fred Hampton. I will never understand why both were slotted into the “best supporting actor” position.  Just baffling.

2022: West Side Story

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Nominees: 

• Coda (actual winner)
• Belfast
• Don’t Look Up
• Drive My Car
• Dune: Part One
• King Richard
• Licorice Pizza
• Nightmare Alley
• The Power of the Dog
• West Side Story

If I didn’t have to choose from this list of nominees, I would award the Oscar to Michael Sarnoski’s Pig and call it an afternoon. A gut-punch of a film, and one of Nicolas Cage’s finest, most understated performances.

From this list, though, we must give the trophy to West Side Story. Leave it to Steven Spielberg to remake one of the great movie musicals and top it in every way. This film is a feast for the senses. Spielberg, cinematographer Janusz Kaminski, and choreographer Justin Peck work together to give us some of the most brilliant visuals I’ve ever seen. Vibrant, kinetic, moving. No offense to Coda, which is a wonderful little film, but this kind of bombastic, confident filmmaking is hard not to laud.

2023: Elvis

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Nominees: 

• Everything Everywhere All at Once (actual winner)
• All Quiet on the Western Front
• Avatar: The Way of Water
• The Banshees of Inisherin
• Elvis
• The Fabelmans
• Tár
• Top Gun: Maverick
• Triangle of Sadness
• Women Talking

Everything Everywhere All at Once may have dazzled with its inventive storytelling and multiverse-spanning narrative, but Baz Luhrmann’s Elvis deserved the Best Picture accolade for its electrifying portrayal of the King of Rock ‘n’ Roll. Elvis is more than just a biopic – it’s a high-octane cinematic experience that pulsates with the energy and charisma of its titular character. Austin Butler’s performance as Elvis Presley is phenomenal, capturing the essence of the legendary musician with a nuanced and deeply emotional portrayal.

Luhrmann’s direction is a visual and auditory feast, with his signature flamboyant style on full display, perfectly complementing Presley’s larger-than-life persona. Elvis balances the glitz and glamour of Elvis’s meteoric rise with the more intimate and poignant moments of his life, painting a comprehensive picture of the man behind the myth.

2024: Barbie

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Nominees: 

• Oppenheimer (actual winner)
• American Fiction
• Anatomy of a Fall
• Barbie
• The Holdovers
• Killers of the Flower Moon
• Maestro
• Past Lives
• Poor Things
• The Zone of Interest

The 2024 nominees are largely dominated by high-concept films and serious dramas, which makes Greta Gerwig’s Barbie all the more refreshing. Oppenheimer is undoubtedly a Best Picture-deserving film, but watching men battle moral dilemmas that can have consequences for all of humankind is a pretty common plot in the world of cinema. On the complete opposite end, rarely does a movie so brilliantly and profoundly explore identity and societal expectations, which is precisely what Gerwig’s Barbie does.

Margot Robbie turned in a career-defining performance as Barbie, and Ryan Gosling as Ken served as the perfect sidekick. Despite eight Oscar nominations, Gerwig’s film walked away with only one victory (Best Original Song). For a colorful, subversive film that points out how feminism still has much more room for progress, it’s hard to dismiss the irony that members of the Academy clearly missed the memo.