Being a member of Generation Z and a film lover is truly a blessed thing. The defining movies of today flaunt a spectacle of sheer awe and astonishment through their technological ability. If I look back to the 1990s, I can find a litany of experimental and daring movies that evolved the form in fascinating new directions. I love the blockbuster brilliance and bravado of the 1980s. I love the hard-edged intensity of the 1970s. But I have a special place in my heart for the classics.
They didn’t have all the mod-cons and technical advancements that the movies of more recent times have leaned on, but that just means their stories and performances had to be perfect; more often than not, they were. Rich with character and soulfulness, the most esteemed classics of early cinema have achieved a timelessness that has seen them age gracefully for almost 100 years, and will see them continue to thrive for 100 more. I’m not making any bold proclamations in calling these films classics, but I am positive I’m not alone in watching them time and time again.
10
‘Dr. Strangelove’ (1964)
The thing I admire most about Stanley Kubrick is his ability to excel in such a vast array of genres, implementing his trademark touches on every story he told, but still willing to lean into appropriate tropes, thus consolidating himself as one of the most versatile filmmakers of all time. He mastered horror, sci-fi, anti-war, crime suspense, and historical epic cinema with aplomb, but the movie of his that I tend to revisit the most is his 1964 Cold War political satire, Dr. Strangelove.
Peter Sellers is magnificent in each of his three roles, but I find his performative punch is matched by the impressionable hilarity of George C. Scott’s aggressively American portrayal of Gen. “Buck” Turgidson, a performance I consider among the outright best in comedy cinema. Furthermore, the sharpness of the writing is something to behold, flaunting an acidic, skewering wit that few movies since have been able to replicate. Every viewing brings the discovery of a great gag or a performance decision, making Dr. Strangelove an endlessly rewatchable comedy classic that, in my opinion, stands tall among the greatest movies ever made.
9
‘Seven Samurai’ (1954)
With a runtime close to three-and-a-half hours, it is often difficult to find a window of ample time to watch Seven Samurai, but when one presents, it is a great movie to revisit and enjoy again. I’m not making any bold claim by saying that Akira Kurosawa is one of the greatest filmmakers of all time, a pioneering genius of shot composition and visual storytelling. The 1954 epic stands as his magnum opus, his most defining achievement (of many). Its story of seven warriors rallying to defend a small farming village from a vicious gang of bandits is as simple as it is glorious, and it set the groundwork for a great many movies that followed.
Its mixture of awe-inspiring action spectacle and contemplative drama is majestic. Indeed, it strikes a perfect balance between audacious and daring set pieces and rich character-focused complexity that delves into ideas of honor and heroism with a razor-sharp understanding of the intricacies of 16th century feudal Japan and the tension between the samurai warriors and the farmers they protect. I find the opening act alone enrapturing, with the assembly of the team and the establishing of character dynamics emotionally engrossing, paving the way for the sense of astonishment and intensity when the fighting starts. Seven Samurai is methodical and mighty, a rollicking action epic of extraordinary depth that gets better with every single rewatch.
8
‘The Kid’ (1921)
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I think Charlie Chaplin probably made better movies—one of which even features higher up on this list—but the charm and sincerity of The Kid is overwhelming. Chaplin is typically brilliant as his iconic Tramp character, a mischievous, street-savvy swindler with a heart of gold, but so much of the movie’s emotional impact rests on the shoulders of seven-year-old Jackie Coogan, who gives arguably the greatest performance from a child star in cinematic history. His wonder, cheekiness, and innocence amplify the same qualities in the Tramp while still complementing his cynicism and wry wickedness.
The great sequences in the film are too many to list, but the biggest standouts for me are the fight scene in the courtyard, the window-smashing scheme and its aftermath with the cop, and, of course, the climactic chase scene in which the Tramp fights with a soul-shattering desperation against the orphanage workers who have come to take the Kid away. That sequence is, for my money, the best use of music that I’ve seen thus far in silent cinema, imbuing the conflict with a palpable heartache and love. The Kid is worthy of multiple rewatches for all these scenes and many more, but it is also my first Chaplin film, so it holds a special place in my heart and makes it a delight to revisit time and time again.
7
‘The General’ (1926)
It may mark another indulgence in my love of silent cinema, but few would deny that The General stands as a film of pioneering brilliance and inspired excellence, soaring to such an extent that it doesn’t just define the dare and talent of the era’s other defining maestro, Buster Keaton, but endures as a triumph of early cinema at large. 2026 marks the centenary of this war-action comedy, and it remains every bit as impressive today as it was in 1926. While the idea of the plucky little hero wanting to fight for the South may not have aged so well, the film’s political sways are completely overshadowed by Keaton’s filmmaking and performative brilliance, the air of sympathetic resonance the movie conjures, and its beating heart of romance and pride amid times of war.
In many respects, The General is cinema’s first true action movie, featuring death-defying stunts and astonishing set pieces in addition to Keaton’s timeless physical comedy to conjure a mesmerizing masterpiece of early cinema that is always a treat to revisit. The sensational train-crash bridge-collapse moment is rousing even today (and even for the umpteenth time), while the sequence with Johnny struggling to load and aim the cannon is a work of comic genius that makes me laugh out loud every time. To be fair, multiple Keaton films nearly made this list for me, with Sherlock Jr., Our Hospitality, and even The Navigator all being favorites of mine. However, The General is his greatest work as well as the one I return to most.
6
‘The Apartment’ (1960)
I must confess that I am not the biggest lover of rom-coms. While I can appreciate the genre’s charm—especially when it’s bolstered by great writing and strong chemistry—I more often than not am left underwhelmed by the imposing presence of formulaic storytelling. That’s just my opinion. The first time I watched The Apartment, I went in suspecting it wouldn’t be for me, but given I love so many other Billy Wilder films and am in awe of his ability to master such a variety of genres, I figured I’d give it a chance. To say I was enraptured from the opening moments would be an understatement, and it has become the ’60s movie I rewatch the most.
Jack Lemmon and Shirley MacLaine are, in my view, the perfect rom-com pairing. They’re both ridiculously endearing and comical, but they both master the dramatic undertones of the movie as well. Throw in Fred MacMurray’s faultless villainous performance and the touching wit and storytelling magnificence of I. A. L. Diamond and Wilder’s screenplay, and The Apartment thrives as a timeless classic of romantic passion, workplace politics, and the complexity of life that is phenomenally funny and surprisingly dark. It’s made even more triumphant by its unforgettable “shut up and deal” finale, marking one of the greatest and most rewarding movie endings of all time.
5
‘Citizen Kane’ (1941)
When I first watched Citizen Kane, I must confess, it felt a bit like homework; a prerequisite viewing that I ticked off a watchlist more so than invested in and enjoyed. Watching the classics can be like that sometimes. While I was impressed with its innovation, narrative creativity, and the magnitude of what Orson Welles achieved, I don’t know if I can say I truly loved it. Years later, I decided to revisit it, and each subsequent rewatch since has brought with it a greater immersion into its story and a more refined appreciation of its many qualities.
To this day, I find no character study film has been as bold or as brilliant as Citizen Kane. Its use of non-linear storytelling and unreliable narration as the reporter interviews key figures from Charles Foster Kane’s life in a futile attempt to garner some understanding as to what “Rosebud” truly means is ingenious. The investigation drives the film, but the stories of each character—and their relation to Kane—present an intricate, complex, and sometimes contradictory web surrounding the idea of a great man. I can’t say Citizen Kane is my favorite movie of all time, but its legacy of greatness is well-earned, and every rewatch is not only a marvelous treat but an enthralling lesson of filmmaking excellence as well.
4
‘Ikiru’ (1952)
While the aforementioned Seven Samurai is probably my favorite Kurosawa film, the one I find myself watching the most is 1952’s Ikiru. While so many of the legendary filmmaker’s masterpieces are enormous period epics and scintillating crime thrillers, I’ve always been drawn to the quiet allure of this somber and soulful gem. Kurosawa’s typically ingenious direction and Takashi Shimura’s deft performance of defeat and hope are the film’s defining features, but it is Ikiru’s stunning screenplay structure that resonates with me most when I return to it.
I hesitate to divulge the mid-point narrative turn in too much detail, but the pivot is inspired, allowing the first half of the film to examine a story of renewed belief and a defiant desire to live in the face of death, while the second half becomes a beautiful reflection on the impact one life can have. That gorgeous moment when Kanji sits on the swing in the snow happily singing to himself is a scene that imprints itself on the mind of so many people who watch the movie, a triumphant though bittersweet depiction of contentedness, pride, and reflection. Few films are as powerfully life-affirming as Ikiru, an inspirational tale of resolve and purpose that, every time I watch it, leaves a profound impression on me.
3
‘Casablanca’ (1942)
It is certainly easy to view Casablanca as the epitome of Old Hollywood divinity. The 1942 classic flaunts an effortlessly suave screenplay (making it a favorite of mine), smooth-talking performances (Claude Rains’s turn as Captain Louis Renault is entrenched among the greatest of all time in my view), and the majestic balance between effervescent fluidity and thematic richness. These elements are all staples of the Golden Age of cinema, executed so gloriously that Casablanca is Hollywood at its most stunning and sublime.
In many respects, it is a film you watch for the first time already knowing its biggest moments; its litany of iconic quotes is so embedded in movie pop culture that it is practically impossible to go into it blind. Fortunately, knowing what’s coming doesn’t make Casablanca any less marvelous, a fact that I find to be just as true on the 10th or 11th watch. Still, its greatest triumph in my eyes is the sharpness and impact of its narrative balance, the way it delves into rousing romantic drama and character-focused specificity while presenting a sense of the scope of WWII, while still finding moments for its wicked and wonderful wit to conjure a laugh. Casablanca is a true cinematic gem, a timeless masterpiece defined by its genius across all disciplines, and one of the most easy to rewatch movies ever made.
2
‘It’s a Wonderful Life’ (1946)
To say I’m a huge Jimmy Stewart fan would be an understatement. In my mind, he is not only the epitome of Old Hollywood class and charm, but the most emotionally resonant and hopeful lead the industry has ever seen. His performances in such gems as Mr. Smith Goes to Washington and Harvey are favorites of mine, but the film of his I rewatch the most is It’s a Wonderful Life. Typically getting a run on my TV every Christmas—and maybe once or twice between the festive seasons as well—it is a timeless feat of feel-good cinema, masterful in how it acknowledges the greed, corruption, and bleakness of the world yet still stands as an inspiring tale of basic human decency.
The story alone is marvelous, following honest everyman George Bailey through his life of sacrificial kindness leading up to his attempt to commit suicide in the hope of his family cashing the life insurance. Enter Clarence (Henry Travers), a somewhat oblivious angel with a heart of gold who shows George what his community would be had he never been born. There are so many scenes that make the film a treat to rewatch, from George’s impassioned defiance of Mr. Potter (Lionel Barrymore) after he speaks against his father’s character to the wonderfully witty first conversation between George and Clarence. Alas, the ultimate testament to the movie’s greatness is its grand finale. It is riddled with great moments, but my favorite is always when George reads the inscription in Clarence’s book and, when asked what it is, utters, “That’s a Christmas present from a very dear friend of mine,” with Stewart’s delivery imbued with such incredible warmth and tenderness. Christmas is a time of tradition for many, and when it rolls around again, you can bet your life on the decorations going up, the food being good, and It’s a Wonderful Life being watched again in my house.
1
‘City Lights’ (1931)
When I first started watching Chaplin movies—immediately after I watched the aforementioned The Kid for the first time—I put off watching City Lights. I don’t know why, exactly; perhaps the premise of movies like The Gold Rush, Modern Times, and even talkies like The Great Dictator just appealed to me more on paper. While I love all those movies, it is City Lights that stands as my favorite film of all. Chaplin’s trademark slapstick comedy is not only hysterical throughout, but it does so much to define the drive and determination of his character, whose desperate efforts to secure money for the blind flower girl he loves conjure what is one of the greatest romance movies of all time, in my opinion.
The beauty of silent cinema is that the characters and character dynamics need to communicate so efficiently, often taking on a cartoonish style of physicality. It can be juvenile at times, but in masterpieces like City Lights, it comes across as profoundly pure, even the skullduggery and trickery the Tramp sometimes employs as he tries to grab what he needs. Again, like It’s a Wonderful Life, City Lights is riddled with gorgeous and unforgettable scenes, from the iconic boxing match to Chaplin’s many run-ins with his millionaire friend, who can only remember him while drunk. However, it is the ending that lives on most in my mind. I shan’t spoil it, but it is note-perfect, a heartwarming ode to love that is so sincere and simple, yet unforgettably beautiful. I can comfortably say that City Lights is my most-watched movie of all time, enshrined among the greatest feats of cinematic art.
