Top 50 Movies of the 21st Century
By Cinema Sugar
As 2024 comes to a close, we thought it’d be the perfect time to zoom out from specific genres and spotlight our favorite films from the last 25 years. This was a massive, psychologically brutal, yet ultimately rewarding endeavor given just how many movies we love from this time period and how much we enjoyed revisiting them.
We had just one rule: only one film per director. This admittedly insane limitation forced some very hard choices on us about which film from the illustrious filmographies of David Fincher, Christopher Nolan, Quentin Tarantino, and so many other talented and prolific filmmakers would make the cut. But we liked that self-imposed structure because it allowed us to include more beloved movies that might have otherwise gotten bumped off the list.
Above all, as we explained in the wake of our controversial Top 10 Chicago Movies list, we aren’t interested in making lists that dutifully reflect The Canon or The Criterion Collection or the Highest Average Rating on Letterboxd—we’re interested in the movies within the theme that mean the most to us. Period.
While each of our individual Top 50 lists would look different from this collaborative one, we’re proud to present this group of movies as a collective reflection of our motto: Movies make life sweeter. These 50 movies have certainly made our lives sweeter over the last quarter century, and we can’t wait to hear your thoughts about them. (We even have a list of the omissions we’re sure to hear about the most 😉)
Send your cheers, jeers and, better yet, your own Top 50 list to heycinemasugar@gmail.com or our Instagram or Threads. We’ll be publishing the list 10 movies at a time throughout the month, so check back weekly for the latest batch.
See you at the movies!
50. Road to Perdition
Only Sam Mendes’ second movie, this is a father-and-son road trip story that’s also a revenge thriller. It has one of Tom Hanks’s finest performances and a Thomas Newman score that will haunt me until the end of my days. And it managed to turn heartthrobs Daniel Craig and Jude Law into evil gremlins while featuring a gun show in the rain that hits more like a graphic novel. What more do you need? —Natalie Pohorski
49. Midsommar
If there’s one thing the 21st century has confirmed, it’s that Ari Aster’s mind is a house of horrors. All three of his films are deranged and unforgettable in their own way, but it’s 2019’s Midsommar that takes the flower crown. Not just because of its unshakable imagery (the gut-wrenching opening sequence, the cliff divers, the temple fire), but also because it’s simply one of the most beautiful films I’ve ever seen. Its colorful and intricate production design framed by impeccable cinematography; its mood-altering musical score by Bobby Krlic; and its frank meditations on grief, mortality, and liberation actively work to gain your trust in an environment that cannot be trusted. Midsommar ends on the highest of high notes, sending you out into the world with a permanent expression of horror and elation. If it’s wrong that this excites me, well then hoist me up and call me May Queen. —Kevin Prchal
48. Palm Springs
Nothing like a breezy 90-minute romcom to make you rethink your whole life—and existence itself. Max Barbakow’s time-loop tale is a textbook case of rock-solid execution of a smart, cohesive script, combining a magical amount of comedy, drama, philosophy, and romance with a great cast, led by the charming chemistry of Andy Samberg and Cristin Milioti. When nihilism becomes a little too tempting, Palm Springs is a great reminder to find your own Irvine. (Now release the Blu-ray!) —Chad Comello
47. The Lives of Others
Winner of Best Foreign Language Film at the 2008 Oscars, this Florian Henckel von Donnersmarck film follows a Stasi surveillance officer in early ‘80s East Berlin who spies on a playwright suspected of disloyalty to the Communist Party and soon finds his own loyalties conflicted. Suspenseful and surprisingly moving, it’s both a chilling portrait of life in a totalitarian society and a hopeful mediation on the power of art as a means of telling subversive truths. —Chad Comello
46. Paterson
As a parent of young kids, I can’t help but look with envy at the leisurely lifestyle of Paterson (Adam Driver), a bus driver in Paterson, New Jersey, whose daily routine of working and writing poetry and walking his dog and hanging with his wife is captured by writer-director Jim Jarmusch with a loving, abiding serenity. Balancing artistic pursuits with day jobs and other responsibilities is never easy, but this small yet big-hearted movie shows how to do so with gratitude and grace. —Chad Comello
45. 25th Hour
With only 24 hours left of freedom before starting a prison sentence, Monty Brogan’s (Edward Norton) life comes into sharp focus. A life clouded by crime, misdeeds, and broken relationships. A life which, in a post-9/11 New York City where this film takes place, is fueled by hatred and fear. A life that, as director Spike Lee so elegantly shows, can only present itself as something to cherish when you’re mere hours from leaving it behind. Monty’s mournful yet hopeful path to redemption is deeply felt by his buddies (Phillip Seymour Hoffman, Barry Pepper), his girlfriend Naturelle (Rosario Dawson), and most especially by his father (Brian Cox), who delivers a final monologue for the ages. A monologue that echoes in my head to this day. “This life came so close to never happening...” —Kevin Prchal
44. Jennifer‘s Body
Now ultimately celebrated for its innovative blend of horror, dark comedy, and feminist themes, Jennifer’s Body subverts typical horror movie genre tropes by presenting a nuanced exploration of female friendship and empowerment through its story of a high school girl who becomes possessed and begins preying on her male classmates. The sharp dialogue penned by Diablo Cody and standout performance by Megan Fox (brilliantly weaponizing her own image) challenge societal perceptions of women while simultaneously critiquing the male gaze. Following one of the worst movie marketing failures of all time upon its release in 2009, its cult status has only grown over time, solidifying its place as a pivotal work in contemporary cinema. —Natalie Bauer
43. Top Gun: Maverick
A salute to the movie that saved movies. That revitalized the summer blockbuster and reminded audiences just how thrilling a night at the movies could be beyond the capes and giant blue people. That, in the age of CGI, delivered stunning action sequences featuring real planes, sky, mountains, and people. Whose central emotional storyline between Maverick and Rooster hit like a mach 10 jet to the heart. In a thinly veiled metaphor for Tom Cruise’s place in the film industry, Ed Harris’ character says to him early on: “The end is inevitable, Maverick. Your kind is headed for extinction.” Looking humble yet defiant, he turns calmly to Harris and replies, “Maybe so, sir. But not today.” A defining statement from one of the last truly great movie stars in what will go down as one of the signature action movies of its time. —Kevin Prchal
42. The Cabin In the Woods
This Drew Goddard horror comedy is the stuff dreams are made of: a love letter to horror fans that turns the genre’s cliché tropes into ancient mythology. The comedy is top notch thanks to a Joss Whedon script and performances by Bradley Whitford and Richard Jenkins. Saying anything more would spoil the fun, so we’ll just leave you with “coffee mug bong.” —Natalie Pohorski
41. Bridesmaids
A bride shitting her pants in the middle of the street, a flight attendant named Stove, and a speech beginning with “gracias para vivar en la casa”—these are just a couple of highlights in what might be one of the funniest movies of all time, not to mention the movie responsible for a Wilson Phillips comeback. It’s also a beautiful tribute to female friendships and one of the most honest portrayals of depression and adulthood on screen. —Natalie Pohorski
40. Amelie
This fanciful Parisian fairytale follows a lonely girl with a big heart whose world is busted open when a family heirloom sets her on a quest to help others. A quirky and delightful parable about the risks of love, Amelie bursts with color and spinning cameras, underscored by the music of Yann Tiersen. Maybe it was just a Millennial moment, but we think it’s one worth remembering. —Natalie Pohorski
39. Spider-Man: Into the Spider-Verse
Gloriously resplendent in scope and style but always grounded in the immediate concerns of Miles Morales and his archetypal Spidey struggles, Into the Spider-Verse’s exhilarating, comics-infused sensibility packs every moment with exquisite artistic detail and emotional stakes that beckon us into a vividly rendered vision, which has already instigated a much-needed sea change in film animation and superhero movies. —Chad Comello
38. Brick
Writer-director Rian Johnson’s electrifying debut feature is a whodunit with all the trappings of the genre that strangely yet fittingly take place among teens acting and speaking way beyond their years. Johnson’s self-assured style and snappy dialogue would foretell his later foray into murder mystery with Knives Out, which is excellent in its own ways but still a descendant of Brick and its straight-no-chaser gumption. —Chad Comello
37. The Zone of Interest
In Jonathan Glazer’s The Zone of Interest, it’s perhaps easier to see yourself in the characters than it is to see a family operating a concentration camp in Auschwitz. The grandmother, casually perusing the garden. The kids being kids, playing with toy soldiers, making out, and swimming in the river. The mother, beaming with pride at the home and life she’s built for her family. And the father, warmly embracing animals and going about his duties as plainly as a landlord. Shot in all single frames so as to not jolt viewers from sitting with and contemplating every scene, it makes a powerful plea for our contributions in a world that’s only as evil as we allow it to be. —Kevin Prchal
36. Lincoln
This is a biopic done right: not as a shallow, decades-spanning survey with bad aging makeup, but as a focused, intentionally contained slice of life that captures its subject and his times with just the right mix of reverence and rigor. Daniel Day-Lewis deservedly won Best Actor for his turn as the 16th president, but the movie’s star-studded surrounding cast helped elevate what could have been a hagiographic bore into a Mount Rushmore-worthy triumph. —Chad Comello
35. Grizzly Man
“It is not so much a look at wild nature as it is an insight into ourselves, our nature.” So narrates Werner Herzog in this stranger-than-fiction documentary charting environmentalist Timothy Treadwell’s sojourns to and ultimate demise among the grizzly bears of Alaska’s Katmai National Park. Using Treadwell’s own footage adds to the film’s palpable dread that builds through his every bear interaction and off-kilter monologue, while forcing us to reckon with hard questions: What is humanity’s place in nature? What is nature’s place among humanity? The answers, as Treadwell and Herzog discovered, demand a journey into the wilderness. —Chad Comello
34. Eternal Sunshine of the Spotless Mind
In a profound exploration of love, memory, and the human condition, director Michel Gondry and writer Charlie Kaufman orchestrated a film that masterfully intertwines a unique narrative structure with surreal visuals. Taking the audience on an emotional journey through the mind of Joel (a markedly subdued Jim Carrey) as he undergoes a procedure to erase memories of his failed relationship with Clementine (the wild and resilient Kate Winslet), this inventive premise raises poignant questions about the nature of love and the value of our memories, both painful and joyful. Its blend of science-fiction and romance, combined with powerful performances and a haunting score, resonates deeply, making it not only a cinematic masterpiece but also a reflective meditation on the complexities of intimacy and the desire to hold onto the past. —Natalie Bauer
33. Spirited Away
No one builds a world from the ground up quite like Hayao Miyazaki. This flick has everything: floating faceless ghosts, a giant spider man who feeds coal into a boiler room fire, a boy who is really a dragon. Miyazaki’s imagination is as boundless as his plots, and Spirited Away may just be his greatest tale of them all. —Dylan Stuckey
32. Moulin Rouge!
Where to begin with this dark delight, this hopeless romance? It’s an addicting musical drama filled with cover songs and drug-induced sequences that only Baz Luhrmann could piece together into something coherent and spectacular. The Elephant scene is a comedic wonder and the “El Tango de Roxanne” sequence is a master class in editing. This film earns its place next to the classics because it breathed new life into the genre after decades ruled almost exclusively by Disney. —Natalie Pohorski
31. Lost In Translation
Widely regarded for its poignant exploration of loneliness and companionship in a globalized world, director Sofia Coppola has created a film that beautifully captures the unexpected bond formed between two lost souls against the backdrop of a vibrant yet isolating Tokyo. Its subtle storytelling, combined with striking cinematography and an evocative soundtrack, creates an immersive atmosphere that resonates with anyone who has ever experienced this simultaneously very precise yet universal feeling of solitude. Its themes of existential yearning and fleeting intimacy are skillfully rendered, making it a timeless reflection on the complexities of human connection. The chemistry between Bill Murray and Scarlett Johansson, along with Coppola's delicate direction, elevates the film to a meditative exploration of the human experience, solidifying its place as a modern classic. —Natalie Bauer