The Top Ten Best Picture Oscar winners of the 21st Century

As we enter the fall, the dawn of a new Oscar season is upon us. As the first year of a new decade, it will be the most unusual season of our lifetimes. With COVID-19 still impacting the industry, it’s becoming harder to see how a normal ceremony can happen in early 2021. It makes us nostalgic for simpler times when movie theaters were open, fall festivals were running regularly, and the Oscar campaigns were in full swing. You know, like last year. 

With all of that in mind, we’re at the 20-year mark of this century already. And even though 2020 might be a wash, the best moment of the year for many in the film community was Parasite winning Best Picture. It was a moment to celebrate the love of cinema and one of the best films of the decade. So with today’s top ten list, we are looking back at simpler times and counting down the best Best Picture winners of the 21st Century. Though there are only 20 movies to choose from, it wasn’t too hard to narrow down as the ten films below stand head and shoulders above the rest. And don’t worry, Crash and Green Book aren’t anywhere near this list. 

10. The Departed (Warner Bros – 2006)

Starting off this list is a crime picture from one of the greatest directors of all time, Martin Scorsese. The Departed follows two cops entangled in the Boston Police department. One is deep undercover within the Irish mob, and the other is the mob’s mole inside the detective’s division. Though being his most contemporary crime film to date, Scorsese contributes another highly entertaining entry into a genre he became a legend in. Led by excellent performances from Leonardo DiCaprio, Matt Damon, Mark Wahlberg, and Jack Nicholson, we go along a cat and mouse thriller with plenty of blood and bullets usually found in a Scorsese picture. The Departed not only won Best Picture but finally secured Martin Scorsese’s long overdue Best Director win. 

9. Spotlight (Open Road Films – 2015) 

Throughout this list, there will be movies mentioned that tackle significant issues. In many people’s opinion, the more relevant the film is, the better its chances to win Best Picture. This was the case in 2015 when the Academy awarded Tom McCarthy’s Spotlight the top prize. Following the Boston Globe’s investigation into the Catholic Church’s cover-up of child molestation, we see how far the rabbit hole goes and how much work these journalists have to put in to uncover the trust. With a stacked ensemble and a detailed script, Spotlight is on par with All the President’s Men as one of the best films to examine systemic injustices.

8. Million Dollar Baby (Warner Bros – 2004)

Clint Eastwood is a staple in American cinema. From starring in dozens of motion pictures to moving behind the camera, Eastwood has made a career out of entertaining audiences spanning close to 60 years. But his best work in front and behind the camera came in 2004 with his sports drama Million Dollar Baby. Eastwood plays a hard headed trainer who teaches a motivated young woman (Hilary Swank) how to become a boxer. Tough at first, their relationship blossoms into a real close bond, leading to a heartbreaking decision no one should have to make. Million Dollar Baby is more than a boxing movie; it’s about lonely people finding someone to relate to in this sad world.

7. The Hurt Locker (Summit Entertainment- 2009)

For most of this century, filmmakers have been making stories set on the topic of the United States war in Iraq. In 2008, director Kathryn Bigelow and screenwriter Mark Boal made the most honest depiction of America’s fight in the Middle East. Following a unit of bomb disposal soldiers, we examine their day-to-day activities and the constant threats they face. Given their stressful jobs, these men constantly change in front of our very eyes, not always for the best. In the end, all they know is the war, and they continue to sign up for more tours, hoping to fill the void of battle. Between Bigelow’s breathtaking direction and Boal’s blunt script, you won’t need to see any other film like it once the credits start rolling.

6. 12 Years a Slave (Fox Searchlight – 2013)

There is nothing more horrific and shameful in American history than our countries’ participation in slavery. In Steve McQueen’s 12 Years a Slave, we are shown the rawist display of slavery since Roots. Based on a true story, we follow the journey of Solomon Northup (Chiwetel Ejiofor), a free man who is kidnapped against his will and sold into slavery. Over the length of the film, we see Solomon treated horribly with so much violence and cruelty, it will make you wonder how our world has any humanity left. Though a brutal watch, McQueen made a critical, gut-wrenching account of our shameful past we should all see at least once.

5. Chicago (Miramax – 2002)

Based on the output from this century, it’s tough to make a musical everyone loves anymore. While many have released over the last 20 years, few have been able to match the quality of Rob Marshall’s Chicago. Based on the Tony award-winning musical, it follows two murderesses (Renée Zellweger, Catherine Zeta-Jones) on death row, who fight each other for fame and the attention of their slick lawyer (Richard Gere). With memorable musical numbers, stellar production designs, terrific costumes, and lavish performances, Chicago ranks as one of the best movie musicals of all time. No musical has won Best Picture since it won, proving it’s going take something pretty special to come along for the genre to win again.

4. No Country for Old Men (Miramax – 2007)

In the Coen Brothers’ No Country for Old Men, good and evil collide in epic proportions. Based on the novel by Cormac McCarthy, we witness a bloody battle between a local hunter (Josh Brolin) and a mercenary (Javier Bardem) over a case of money found in West Texas. Hot on their trail is a local sheriff (Tommy Lee Jones) looking to stop them before more people are harmed. It’s the darkest material the Coens have ever covered in their long careers, while also their most introspective. In a world filled with violence and sorrow, does good even have a chance to survive? Are life’s essential choices as simple as flipping a coin? These questions and more left for the audience to decide, leaving us coming back for more of this twisted western.

3. Parasite (Neon – 2019)

The most recent winner on this list is also an instant classic from director Bong Joon-Ho. Parasite invites us into the lives of two families in South Korea, one rich and the other poor. Beyond the basic setup, you really can’t get into too much detail about the film, consider its chock-full of twist and turns you need to see to believe. Ultimately, Parasite is an important look at class discrimination within our world and how hard it is to climb the social ladder. It mixes humor with rounded messages about greed and how we see each other. Though a South Korean film, Parasite speaks to the global economic issue of the rich eating the poor, and the poor needing to fight back to survive. 

2. The Lord of the Rings: The Return of the King (New Line Cinema – 2003)

Hollywood has always celebrated the epic at the Oscars. Whether it’s Lawrence of Arabia, Gone with the Wind, Ben-Hur, they are a culmination of grand storytelling mixed with tons of craft and hard work. Within this century, the best epic we’ve delivered to cinema’s history was The Lord of the Rings. Adapted from the novels of J.R.R Tolkien, director Peter Jackson successfully made one of the great trilogies of all time. His last chapter, The Return of the King, was the resolution of everything set up within the first two entries, but raised the bar. Far too often, we see our favorite stories unable to stick the landing to their finales. Yet Jackson and company were able to weave everything together masterfully and make another great epic.

1. Moonlight (A24 – 2017)

From the moment it released at the Telluride Film Festival in 2016, Moonlight gained the reputation of being something special. It tells the story of Chiron, a quiet, gay black male, growing up in Miami throughout three crucial moments in his life. Though he struggles to find support in his home life, Chiron finds guidance and acceptance from those who genuinely see him for the beautiful person he is. Director Barry Jenkins and screenwriter Tarell Alvin McCraney used their own stories to create a deeply personal masterpiece. While Moonlight can be seen as a sad story, in the end, it’s about how every person in this world deserves to be loved and cared for like everyone else. We don’t see movies like Moonlight every year, so that’s why it stands out not only as the best film to win Best Picture of this century but as a new classic we will watch and study for years to come.

Ryan McQuade is a film-obsessed writer located in San Antonio, Texas. Raised on musicals, westerns, and James Bond, his taste in cinema is extremely versatile. He’s extremely fond of independent releases and director’s passion projects. Engrossed with all things Oscars, he hosts the Chasing the Gold podcast at InSessionFilm.com. When he’s not watching movies, he’s rooting on all his favorite sports teams, including his beloved Texas Longhorns. You can follow him on Twitter at @ryanmcquade77.