The categories have changed names and identities over the course of the Academy Awards’ history, but since the dawn of the Oscars in 1929, some kind of award has been given out to a year’s best screenplays, split into original and adapted. Logically, over the course of such a long amount of time, several of the greatest scripts ever written for a film have been awarded with an Oscar nomination, and an even more select few have gone on to win.
These are some of the best screenplays ever written, testaments to how to write a good movie. Decorated with meaningful and memorable dialogue, compelling and layered characters, and a well-paced story that keeps things entertaining throughout, these Oscar-winning scripts truly are the stuff of legend. Regardless of how they were actually executed on screen, they’re as flawless as they come on paper.
25
‘Citizen Kane’ (1941)
Praised by some as the single greatest film of Hollywood’s Golden Age, Citizen Kane may or may not live up to that title depending on the viewer’s tastes, but it’s undeniable that it’s far and away one of the era’s most important and groundbreaking cinematic achievements. Co-written, directed, produced, and led by Orson Welles (being his first film, no less!), it sure is one of the greatest character dramas ever filmed.
While the majority of the film’s strength comes from Welles’ impeccable direction and camerawork, the script (co-written by him, and Herman J. Mankiewicz) is nothing to scoff at. Using a clever framing device and a revolutionary non-linear structure, it’s a script with searing thematic power and unexpected complexity considering the time period. It’s an epic story unlike any other cinema has ever told.
24
‘Schindler’s List’ (1993)
Steven Spielberg has made several of the most iconic American films in history, many of them exceptionally written; but most of the time, it’s Spielberg’s direction that mainly makes those works stand out, more so than the script. That’s not the case for Schindler’s List, Spielberg’s masterpiece, where his beautiful direction and Steven Zaillian’s legendary screenplay work together in perfect balance.
This is one of the best biopics of all time, a deeply intricate Holocaust drama that never avoids the complexity of its historical setting or of its subject, even if a bit more moral ambiguity in the depiction of Oskar Schindler might have benefited the story. Deeply emotional, multi-layered, and well-researched, this is undoubtedly one of the greatest war films ever made.
23
‘Good Will Hunting’ (1997)
Though they’re obviously best-known for their work as actors, Matt Damon and Ben Affleck‘s first Oscar victories came for the screenplay of Good Will Hunting. What a well-deserved win it was, too. Here we have one of the most beautiful, tender, poignant dramas of the ’90s, largely inspired by Damon and Affleck’s own experiences growing up in their hometown of Cambridge, Massachusetts.
The story’s narrative arc is generally somewhat predictable, but that hardly matters when the story is so rich in emotional detail and the characters are so beautifully fleshed out. Though much of the film’s timelessness comes from its performances (mainly Damon’s and Robin Williams‘ Oscar-winning turn), it’s the brilliantly written dialogue and the emotional power of each individual character moment that realy makes this movie pop off.
22
‘Amadeus’ (1984)
Wolfgang Amadeus Mozart needs no introduction, and as one of the greatest period pieces and greatest biopics of all time, neither should Amadeus. Written by Peter Shaffer, Miloš Forman‘s magnum opus is cinema’s quintessential tale of rivalry, a story of genius that definitely takes some creative liberties with the historical facts behind its story, but all of them are to the benefit of the narrative.
There’s no getting around it: Amadeus is mesmerizing even before it’s brought from page to screen. While the technical qualities of the picture elevate it to incredible heights, the script is just as strong, with one of the most creative and emotionally resonant framing devices in the history of American cinema. That framing alone is enough to make this more than just a story about a famous musician: It’s a provocative portrait of the human experience like few others.
21
‘Sunset Boulevard’ (1950)
Billy Wilder was a chameleon, capable of writing and directing films across all sorts of genres, styles, and tones. For proof, one needn’t look much further than one of his best works: the noir dark comedy Sunset Boulevard, which made meta commentary on Hollywood cool before it became more typical. If there was anything that Wilder was, it was ahead of his time. Co-written by Wilder, Charles Brackett, and D. M. Marshman Jr., this is noir screenwriting perfection.
The dialogue, recited by actors of the stature of Gloria Swanson and William Holden, flows like honey. But it’s the script’s critique of faded fame, the dark side of the American Dream, and Hollywood’s corruption of its aging stars that really packs the most punch. Dark, angry, yet without ever sacrificing its sense of humor, Sunset Boulevard‘s screenplay is one of the best of the ’50s.
20
‘Moonlight’ (2016)
Though there’s an argument to be made that the 21st century so far hasn’t been as great for cinema overall as the best decades of the 20th, that argument is easy to shut down when you bring up films like Moonlight, one of the biggest masterpieces of the last 10 years. It’s a gorgeous coming-of-age in three chapters, raw and poignant but never falling into queer misery tropes. Instead, it’s as hopeful as same-sex romance dramas get.
There’s a tenderness and a care with which Barry Jenkins approaches this story that any lesser writer might have very easily fetishized, elevating it to larger-than-life levels even before it comes off the page. The triptych structure of the story works wonderfully, allowing the audience to appreciate the trajectory of Chiron’s journey of self-discovery with the utmost thematic insight.
19
‘Fargo’ (1996)
No list of the best screenplays of any sort could ever be complete without the Coen brothers, and though the duo have only won two Best Screenplay Oscars (at least half as many as they deserve), they both came for two of the best-written films of their respective decades. But as phenomenal as No Country for Old Men‘s script is, there’s no beating Fargo.
The film’s script is arguably the brothers’ best, full of their usual sardonic wit and quirky-yet-dark tone. It’s a creatively structured, darkly funny meditation on morality in a violent world, with some of the best plotting of any ’90s movie. The puzzling Mike Yanagita detour has split viewers on Fargo‘s script for decades, but aside from that divisive moment, this is an absolutely perfect piece of writing.
18
‘Brokeback Mountain’ (2005)
Ang Lee‘s direction of Brokeback Mountain is what makes it one of the greatest romance movies since Titanic, but Lee would never have gotten there without Diana Ossana and Larry McMurtry‘s script. It’s no coincidence that this is a Western: Subverting the genre’s iconography and syntax at every turn, it turns the hypermasculinity of the American West into a tender tale of a forbidden gay romance.
Lee, Heath Ledger, and Jake Gyllenhaal have never been better, but it’s the script’s richly detailed and emotionally profound narrative that allows them to shine. Working on the relatively sparse basis of Annie Proulx‘s short story of the same title, Ossana and McMurtry crafted a decades-spanning character epic with an ending so beautifully sad that you can’t get to the end of the script without getting the last few pages wet with tears.
17
‘Dog Day Afternoon’ (1975)
Sidney Lumet came into the Hollywood picture right near the tail end of the industry’s Golden Age, and with that experience, he became one of the key figures of the New Hollywood film movement. One of his best films from the era is Dog Day Afternoon, a hectic thriller soaked in a mixture made of equal parts black comedy, character-driven drama, and irresistible suspense.
Much of the film’s strength comes from Lumet’s direction and Al Pacino‘s performance, but the script should never become underrated. Penned by Frank Pierson following intensive research on the real story of the 1972 Chase Manhattan robbery in Brooklyn, the script balances tight pacing, groundbreaking LGBTQ+ representation, and fascinating anti-heroic characters to perfection.
16
‘Annie Hall’ (1977)
You don’t get to become the man with the most Best Screenplay Oscar wins without tremendous amounts of talent, even if you’re someone as creepy as Woody Allen. There’s really no question as to what the writer-director’s best movie is: That would have to be Annie Hall, for which he co-wrote with Marshall Brickman one of the most brilliant rom-com scripts of all time.
Praised for its groundbreaking non-linear structure, its witty fourth wall breaks and internal monologues, and its endlessly neurotic dialogue (an Allen staple), this is one of the funniest movies of the 20th century, no doubt. But full of funny and creative bits as it may be, what has allowed Annie Hall‘s script to age as well as it has is the fact that it’s so deeply analyzable in its comments on love, sexuality, Jewish identity, and modernist ways of thinking.
