10 Best Rom-Coms in Film History

Image via United Artists Published Aug 15, 2026, 12:18 PM EDT Diego Pineda has been a devout storyteller his whole life. He has self-published a fantasy novel and a book of short stories, and is actively working on publishing his second novel. A lifelong fan of watching movies and talking about them endlessly, he writes reviews and analyses on his Instagram page dedicated to cinema, and occasionally on his blog. His favorite filmmakers are Andrei Tarkovsky and Charlie Chaplin. He loves modern Mexican cinema and thinks it's tragically underappreciated. Other interests of Diego's include reading, gaming, roller coasters, writing reviews on his Letterboxd account (username: DPP_reviews), and going down rabbit holes of whatever topic he's interested in at any given point. Sign in to your Collider account Throughout film history, the cinematic art form has evolved in all sorts of unpredictable ways. And through it all, one thing has remained constant: incredible romantic comedies. Pretty much ever since the dawn of cinema as a storytelling medium, audiences have been craving these sorts of stories that remind them of the beauty of love and romance while also managing to get a cackle out of them every few minutes. Rom-coms have greatly evolved throughout the years, too; from the classic screwball comedies of the '30s like It Happened One Night to modern masterpieces like Punch-Drunk Love. This is a genre about as timeless and universally beloved as they come, and over the years, the best rom-com movies in film history have proven why that has always been the case. 10 'Punch-Drunk Love' (2002) Image Via Sony Pictures Releasing After making the cinematic colossus that is Magnolia, the great Paul Thomas Anderson wanted to make something far smaller, simpler, and shorter to recover from the emotional exhaustion of his multi-story epic. A huge fan of Adam Sandler's comedies, he set out to make his next film a 90-minute-long Sandler rom-com. The result? Punch-Drunk Love, proof that PTA doesn't need to go big in order to go all out. Indeed, Punch-Drunk Love may not be a particularly big film in any sense, but that's precisely what makes it a masterpiece. One of the most anxiety-inducing romance movies ever, it's a deeply moving, gleefully offbeat, and irresistibly hilarious masterpiece featuring some of the strongest work of Sandler and Emily Watson's careers. Calling it the best rom-com of the 21st century so far is a take about as hot as the Arctic Circle. 9 'Annie Hall' (1977) Image via United Artists Controversial though he may be, there's no denying the tremendous impact and influence that Woody Allen had not just on the New Hollywood film movement, but also the romantic comedy genre as a whole. He has the most Best Screenplay Oscar nominations and wins out of anyone in history, and his first win in that category—along with a Best Picture win—came for the legendary Annie Hall. It should be pretty much impossible for anyone who loves romantic comedies to watch Annie Hall and not have a phenomenal time doing it. Featuring some of Allen's most vibrantly distinct writing and directing work, as well as Diane Keaton delivering one of the most undeniable Best Actress Oscar-winning performances ever, this '70s classic was absolutely revolutionary in its messy, chaotic, realistic look at modern relationships. Collider Exclusive · Oscar Best Picture Quiz Which Oscar Best PictureIs Your Perfect Movie? Parasite · Everything Everywhere · Oppenheimer · Birdman · No Country Five Oscar Best Picture winners. Five completely different visions of what cinema can be — and what it can do to you. One of them is the film that was made for the way your mind works. Ten questions will figure out which one. 🪜Parasite 🌀Everything Everywhere ☢️Oppenheimer 🐦Birdman 🪙No Country for Old Men FIND YOUR FILM → 01 What kind of film experience do you actually want? The best movies don't just entertain — they leave something behind. ASomething that pulls the rug out — that makes me think I'm watching one kind of film and then reveals I'm watching another entirely. BSomething overwhelming — funny, sad, absurd, and genuinely moving, all at once. CSomething grand and weighty — a film that makes me feel the full scale of what I'm watching. DSomething formally daring — a film that pushes what cinema can even do. ESomething lean and relentless — pure tension with no wasted frame. NEXT QUESTION → 02 Which idea grabs you most in a film? Great films are driven by a central obsession. What's yours? AClass, inequality, and what people are willing to do when desperation meets opportunity. BIdentity, family, and the chaos of trying to hold your life together when everything is falling apart. CGenius, moral responsibility, and the catastrophic weight of a decision you can never take back. DEgo, legacy, and the terror of becoming irrelevant while you're still alive to watch it happen. EEvil, chance, and whether moral order actually exists or if we just tell ourselves it does. NEXT QUESTION → 03 How do you like your story told? Form is content. The way a story is shaped changes what it means. AGenre-twisting — I want it to start in one lane and migrate into something completely different. BMaximalist and genre-blending — comedy, action, drama, sci-fi, all in one ride. CEpic and non-linear — cutting between timelines, building a mosaic of cause and consequence. DA single unbroken flow — I want to feel like I'm living it in real time, no cuts to safety. ESpare and precise — every scene doing exactly what it needs to do and nothing more. NEXT QUESTION → 04 What makes a truly great antagonist? The opposition defines the protagonist. What kind of opposition fascinates you? AA system — invisible, structural, and almost impossible to fight because it has no single face. BThe self — the ways we sabotage, abandon, and fail the people we love most. CHistory — the unstoppable momentum of events that no single person can stop or redirect. DThe industry — the machinery of culture that chews up talent and spits out irrelevance. EPure, implacable evil — a force so certain of itself it becomes almost philosophical. NEXT QUESTION → 05 What do you want from a film's ending? The final note is the one that lingers. What do you want it to sound like? AShock and inevitability — a conclusion that recontextualises everything that came before it. BEarned emotion — I want to cry, laugh, and feel genuinely hopeful, even if the world is a mess. CDevastation and grandeur — an ending that makes me sit in silence for a few minutes after. DAmbiguity — something that leaves enough open that I'm still thinking about it days later. EBleakness — an honest refusal to pretend the world is tidier than it actually is. NEXT QUESTION → 06 Which setting pulls you in most? Where a film takes place shapes everything — mood, stakes, what's even possible. AA gleaming modern city with a hidden underside — beauty masking rot, wealth masking desperation. BA collapsing suburban life that opens onto something infinite — the multiverse of a single ordinary person. CThe corridors of power and science at a world-historical turning point — where decisions echo for decades. DThe grimy, alive chaos of New York and Hollywood — fame as both destination and trap. EVast, indifferent landscape — desert and highway where violence arrives without warning or reason. NEXT QUESTION → 07 What cinematic craft impresses you most? Every great film has a signature — a technical or artistic element that makes it unmistakable. AProduction design and mise-en-scène — every frame composed to carry meaning beneath the surface. BEditing and tonal control — the ability to move between registers without losing the audience. CScore and sound design — music that becomes inseparable from the dread and awe of what you're watching. DCinematography as performance — the camera not recording events but participating in them. ESilence and restraint — what's left unsaid and unshown doing more work than any dialogue could. NEXT QUESTION → 08 What kind of main character do you root for? The protagonist is the lens. Who you choose to follow says something about you. ASomeone smart and resourceful who makes increasingly dangerous decisions under pressure. BSomeone overwhelmed and ordinary who turns out to be capable of something extraordinary. CA brilliant, tortured figure whose gifts and flaws are inseparable from each other. DA self-destructive artist whose ego is both their superpower and their undoing. EA quiet, principled person trying to make sense of a world that has stopped making sense. NEXT QUESTION → 09 How do you feel about a film that takes its time? Pace is a choice. Some films sprint; others let tension accumulate slowly, deliberately. AI love a slow build when I know the payoff is going to be seismic — patience for a devastating reveal. BGive me relentless momentum — I want to feel breathless and emotionally spent by the end. CEpic runtime doesn't scare me — if the material demands three hours, give me three hours. DI want it to feel propulsive even when nothing is technically happening — restless energy throughout. EDeliberate and unhurried — I want dread to accumulate in the spaces between the action. NEXT QUESTION → 10 What do you want to feel walking out of the cinema? The best films leave a mark. What kind of mark do you want? AUnsettled — like I've just seen something I can't fully explain but can't stop thinking about. BMoved and energised — like the film reminded me what actually matters and gave me something to hold onto. CHumbled — like I've been in the presence of something genuinely important and overwhelming. DExhilarated — like I've just seen cinema doing something it's never quite done before. EHaunted — like a cold, quiet dread that stays with me for days. REVEAL MY FILM → The Academy Has Decided Your Perfect Film Is…Your answers have pointed to one Oscar Best Picture winner above all others. This is the film that was made for the way your mind works. ParasiteYou are drawn to films that operate on multiple levels simultaneously — that begin in one genre and quietly, brilliantly migrate into another. Bong Joon-ho's Parasite is a film about class, desire, and the architecture of inequality that manages to be darkly funny, deeply suspenseful, and genuinely shocking across a single extraordinary running time. Your instinct is for cinema that hides its true intentions until the moment it's ready to reveal them. Parasite is exactly that — a film that rewards close attention and punishes assumptions, right up to its devastating final image. Everything Everywhere All at OnceYou want it all — and this film gives you all of it. The Daniels' Everything Everywhere All at Once is one of the most maximalist films ever made: action comedy, multiverse sci-fi, family drama, existential crisis, and a genuinely earned emotional core that sneaks up on you amid the chaos. You are someone who responds to ambition, who doesn't want cinema to choose between being entertaining and being meaningful. This film refuses that choice entirely. It is overwhelming by design, and its overwhelming nature is precisely the point — because the feeling of being crushed by infinite possibility is exactly what it's about. OppenheimerYou are drawn to cinema on a grand scale — films that understand history not as a backdrop but as a force, and that place their characters inside that force and watch what happens. Christopher Nolan's Oppenheimer is a film about the terrifying gap between what we can do and what we should do, told with the full weight of one of the most consequential moments in human history behind it. You want your films to feel important without feeling self-important — to earn their ambition through sheer craft and the gravity of their subject. Oppenheimer does exactly that. It is enormous, complicated, and refuses easy comfort. BirdmanYou are drawn to films that foreground their own construction — that make the how of the filmmaking part of the what it's about. Alejandro González Iñárritu's Birdman, shot to appear as a single continuous take, is cinema examining itself through the cracked mirror of a fading actor's ego. You respond to formal daring, to the feeling that a film is doing something that probably shouldn't be possible. Michael Keaton's performance and Emmanuel Lubezki's restless camera create something genuinely unlike anything else — a film that is simultaneously about creativity, relevance, self-destruction, and the impossibility of ever truly knowing if your work means anything at all. No Country for Old MenYou are drawn to cinema that trusts silence, that refuses to explain itself, and that treats dread as a form of meaning. The Coen Brothers' No Country for Old Men is a film about the arrival of a new kind of evil — implacable, arbitrary, and utterly indifferent to the moral frameworks we use to make sense of the world. It is one of the most formally controlled films ever made, and its controlled restraint is what makes it so terrifying. You want your films to haunt you, not comfort you. You are not interested in resolution if resolution would be dishonest. No Country for Old Men is honest in a way that most cinema never dares to be. ↻ RETAKE THE QUIZ 8 'Roman Holiday' (1953) Image via Paramount Pictures Directed by the legendary William Wyler, one of the biggest icons of Golden-Age Hollywood filmmaking, and co-written by John Dighton and the then-blacklisted Dalton Trumbo, Roman Holiday is one of the best romantic movies ever made. It stars Gregory Peck and Audrey Hepburn, who together make up one of the most iconic romantic pairings in the history of romantic comedies. But as perfect as Peck and Hepburn are in their roles, they're far from the only thing that Roman Holiday has going for it. It's a beautiful, lavish, and genuinely funny delight that was actually shot on location in Rome, making for backdrops about as gorgeous as the story they accompany. It's comfort food in its purest cinematic form, the kind of classic that everyone—regardless of how they typically feel about rom-coms—should check out at least once. 7 'To Be Or Not to Be' (1942) As the years have passed, many movies from 1942 have become undeniable classics, and To Be Or Not to Be is most definitely among the best. Directed by Ernst Lubitsch, this Hollywood gem is one of the best movies that were made in Hollywood during World War II. As far as superlatives go, there are plenty that apply here: We're talking about one of the best dark comedies of all time, one of the best WWII movies of all time, and definitely one of the best rom-coms of all time. Back in 1942, many found the film and its satirization of the Nazis to be in awfully poor taste. It took years for audiences to fully warm up to Lubitsch's masterpiece, but nowadays, it's widely recognized as what it always was: an impeccably produced, masterfully written, and irresistibly amusing satirization of an inherently ridiculous ideology which only keeps getting better with age. 6 'Chungking Express' (1994) Image via Miramax Hong Kong auteur Wong Kar-wai is one of the most beloved cult filmmakers of his generation, the mind behind several of the best movies since the '90s. One of them is undoubtedly Chungking Express, one of those romantic movies from the '90s that are perfect from start to finish. It's a multi-story narrative much in the same vein as that same year's Pulp Fiction, and it's an arthouse classic that has aged every bit as well. It's not your traditional romantic comedy by any stretch of the imagination. Purely driven by Wong's auteurial vision, it's a wonderfully naturalistic and aesthetically unique dramedy about the hope of finding love in a society of increasing isolation, alienation, and loneliness. Hauntingly timeless and poetic, it's perfect for those who find infectiously joyful rom-coms a bit too saccharine. 5 'Some Like It Hot' (1959) Billy Wilder was one of the greatest and most important filmmakers of Hollywood's Classical era, a director who was constantly far ahead of his time and never afraid to push the limits of the period. One of his most boundary-pushing masterpieces was released right at the tail end of Hollywood's Golden Age: Some Like It Hot, one of the most perfect Marilyn Monroe movies of all time. Also starring Tony Curtis and Jack Lemmon, this essential classic is a cornerstone of the entire rom-com genre. With its surprisingly nuanced exploration of themes like gender and sexuality having aged like fine wine, it still feels like an unexpectedly modern screwball comedy today, bolstered by its exceptional performances and the pitch-perfect screenplay by Wilder and I. A. L. Diamond. 4 'The Apartment' (1960) Image via United Artists As if any more proof were needed that there has never been any master of the big screen quite like Billy Wilder, there's also his Best Picture Oscar-winning The Apartment, which is also one of the greatest rom-coms in history. Penned by him and Diamond as well, it's a layered exploration of romantic love in the modern day that still feels poignantly timely and relevant today. One of those dramedy masterpieces with great acting, The Apartment works flawlessly in pretty much all areas: It's romantic yet beautifully realistic, it's impeccably performed, it's perfectly written, and it's a visual delight. With its balance between deep pathos and irresistible Wilder humor working like a charm from beginning to end, it's still considered one of the best motion pictures of the '60s. 3 'Singin' in the Rain' (1952) Image via Loew's Inc. There are many genres that have historically gotten along quite well with rom-com filmmakers, and one of the main ones is the musical. Calling Singin' in the Rain one of the most universally beloved musical movies of all time is the understatement of the century, seeing as this Gene Kelly and Stanley Donen masterpiece may very well be the greatest musical in the history of cinema. There's something here for pretty much everyone: Die-hard cinephiles will be delighted by the way the film depicts the mayhem of Hollywood's transition to sound, hopeless romantics will inevitably be won over by Don and Kathy's enemies-to-lovers arc, and those just looking for a few good tunes will be treated to some of the catchiest in the history of cinema. 2 'It Happened One Night' (1934) Image via Columbia Pictures Frank Capra was another filmmaker from Hollywood's Golden Age who was never afraid to push the limits of what the era allowed, particularly when it came to dancing around the censorial rules established by the Hays Code. Before the Code was strictly enforced, however, Capra made the Best Picture Oscar-winning It Happened One Night, one of those comedy movie masterpieces that became the blueprint for the entire genre. But aside from being an exquisitely meta critique of the censorship that it prophetically predicted would soon rule Hollywood, It Happened One Night is also a delectably romantic and incredibly funny masterpiece in and of itself. Led by Claudette Colbert and Clark Gable, who deliver two of the best comedic performances of the entire 20th century, this classic is widely regarded as one of the greatest feature films ever made—for good reason. 1 'City Lights' (1931) Image via United Artists There is no bigger poster boy of silent cinema than Charlie Chaplin, whose silent comedies are all still essential viewing for anyone and everyone interested in that era of cinema. There is no Chaplin masterpiece, however, more essential than the delightful rom-com City Lights. It's almost a century old by this point, yet it's still the most timelessly charming romantic comedy the big screen has ever seen. One of those must-see classics that are under 90 minutes, City Lights makes up for what it lacks in dialogue with tons of heart, humor, and beauty. Chaplin was always one of Hollywood's biggest sentimentalists, without ever allowing his work to get sappy. Balancing irresistible romance with hysterical slapstick and some of the most memorable set pieces in the history of Golden-Age Hollywood, this rom-com is easily the greatest in film history. City Lights Release Date March 7, 1931 Runtime 87 Minutes