Steven Soderbergh – 2001
New York Times Ranking: 71

The most commercial, flashiest, and jazziest film on this list, Soderbergh’s heist-drama-thriller is endlessly rewatchable fun. Starring an impressively large cast of Hollywood stars, including Matt Damon, George Clooney, Brad Pitt, and Julia Roberts, it’s hard not to love “Ocean’s Eleven.” Two hours that fly by in an instant, it’s the peak of Soderbergh’s pizzazz-filled crime stories. The film remains the pinnacle of all blockbuster crime projects.

David Fincher – 2011
New York Times Ranking: Unranked

“The Girl with the Dragon Tattoo” is the most underrated film from masterful thrillmaker and writer-director David Fincher. As disturbing as they come, with plenty of graphic gore and sexual violence, the film isn’t an easy watch, but it is an important one. Starring one of the most underseen performances from one of our most successful character actors, Daniel Craig, and another solid performance from high-brow Hollywood 2010s favorite actress, Rooney Mara. Another one of Fincher’s vile crime stories, and narrowly his best, there are few films as discomforting to watch as this one.

Hayao Miyazaki – 2001
New York Times Ranking: 9

As the only animated film on this list, “Spirited Away” is the go-to “great” animated film for most critics (even in its New York Times ranking). But the movie more than deserves its acclaim. A beautifully rendered, complex, hand-drawn coming-of-age story, there’s something for everyone to love in “Spirited Away”. A work that has been copied countless times, but not once matched, there will never be another film like it. The greatest movie from Japan’s greatest animator, it’s easy to see how it finds itself a spot on this list, and on so many lists over the years.

Noah Baumbach – 2019
New York Times Ranking: Unranked

Noah Baumbach is far and away one of the most consistent directors of his generation, but his peak clearly was with his masterpiece, “Marriage Story.” Coming right in the midst of a cinematically incredible 2019, “Marriage Story” features a powerful script and two legendary performances by two of our great actors: Scarlett Johansson and Adam Driver. The height of Baumbach’s themes of emotional isolation and social disconnection, and the perfect late-career role for both of its stars, “Marriage Story” could not have been more perfectly timed.

Berry Jenkins – 2016
New York Times Ranking: 5

The best screenplay on this list, Barry Jenkins’ masterfully realized “Moonlight,” is among the most emotionally impactful films ever made. A pure, simple, beautiful story that rides on the backs of two magnificent performances from Trevante Rhodes and Andre Holland. The film’s excellence has helped it escape the messy legacy of the messy 2017 “Moonlight” – “La La Land” Oscars mix-up, which a lesser film would not be able to do. The screenplay sets a new standard for well-written scripts in the 21st century; unfortunately, that standard has rarely been met since.

Christopher Nolan – 2023
New York Times Ranking: 65

The billion-dollar, Best-Picture-winner, three-hour, culture-shifting classic Hollywood “great man” film was the first film I thought of when making this list. Christopher Nolan’s masterpiece, “Oppenheimer,” is one of the most powerful films I’ve ever had the pleasure of viewing in a theater. The practically-made Trinity Test scene may be the best fifteen minutes of filmmaking on this list, and the last courtroom drama, black-and-white ninety minutes, is the best writing Nolan has ever done. There’s not much left to say about “Oppenheimer”, as it has been the subject of countless pieces of film criticism and theory for the past few years, but it cements itself towards the top of this list.

Michael Mann – 2004
New York Times Ranking: Unranked

One of the hottest takes on this list, and the most underrated (and the best) action-thriller of the quarter-century, Michael Mann’s masterpiece “Collateral” is an incredibly thrilling cinematic experience, the likes of which we haven’t seen since. Starring Jamie Foxx at the peak of his powers and pre-god-complex Tom Cruise, it features some of the most understated acting on this list. Mann’s two-hour, digitally-shot, Los Angeles crime micro-epic is in brilliant conversation with the rest of Mann’s filmography, namely the marvelous “Heat”. Although it’s a near-perfect film, the strongest element is by far the cinematography by Dion Beebe and Paul Cameron. It beautifully displays LA nightlife using Mann’s classic blue washes and features striking red light. An action-thriller that perfects both genres is rarely seen, so Mann’s work here has to be rewarded as one of the finest films of the 21st century.

Park-Chan Wook – 2016
New York Times Ranking: Unranked

Another incredibly underrated feature, “The Handmaiden” is a masterpiece from South Korean genre maestro Park Chan-Wook—an intricately crafted tale of liberation, sexuality, deceit, love, and nationality. Chan-Wook revels in the malice behind mankind’s every decision and distorts and twists the male gaze in an absurdly brilliant fashion. Every shot could be a beautiful photograph, a cherry blossom tree in a manicured yard, two women backed by a violet sunset embracing as they finally achieved freedom, a puppet and a handmaiden intersecting midair. These are all pictures Chan-Wook doesn’t just show us, but paints for us, letting the viewer sit in every frame. “The Handmaiden” is incredible artistic filmmaking in its highest form.

Celine Song – 2023
New York Times Ranking: 83

Although Celine Song isn’t quite the promising director she was when the film came out (with the mixed reception to “Materialists” and her being penned to write the sequel to “My Best Friend’s Wedding”), her debut film, “Past Lives,” is still transcendent. “Past Lives” has an excellent level of patience within its storytelling that is rarely found in cinema today. It offers such a beautiful and intimate contemplation of love, fate, loneliness, and confronting your future while embracing your past. It doesn’t hammer the viewer over the head with its themes, but instead displays them in a careful and quiet manner, so that the viewer has nothing to do but experience them. Its color palette, cold and grey with the occasional presence of a warm orange light, accompanies and develops the themes incredibly thoughtfully. Celine Song writes an excellent debut script that asks the viewer if love is destined or a choice, with three incredible performances from Greta Lee, Teo Yoo, and John Magaro to enhance it.

Paul Thomas Anderson – 2007
New York Times Ranking: 3

This was the toughest choice to make, not because it’s not easily one of the best films of the quarter century, but because the decision between “There Will Be Blood” and three other Paul Thomas Anderson films (“The Master”, “Punch-Drunk Love”, and “Phantom Thread”) was incredibly difficult. “Punch-Drunk Love” is my favorite of the bunch, “Phantom Thread” is the tightest, and “The Master” is the most emotional, but there’s nothing that compares to the sheer scope and power of “There Will Be Blood”. Headlined by an all-world Daniel Day-Lewis performance and a bone-chilling score, “There Will Be Blood” is a nearly three-hour cynical American epic that is amongst the greatest films of all time, but still endlessly indebted to countless films that came before it. “There Will Be Blood” is a true masterclass of filmmaking, the greatest film from our greatest living director, and the best film of the past 25 years.