Aaron Sorkin’s The Trial of the Chicago 7 hits Netflix today, and while it’s only his second directorial effort, he’s still been one of the most prominent storytellers in Hollywood for the last three decades. Along with massive TV shows like The West Wing and plays like To Kill A Mockingbird, Sorkin has written screenplays for nine movies.
Some consider Sorkin the greatest living American screenwriter, while others dismiss him as overly indulgent and out of touch. It’s certainly true that not all of his scripts translate into great films, and some of them may not even be great scripts in the first place. But all of Sorkin’s work is utterly engaging, and his voice is one of the most distinct in modern American cinema. The writer injects a unique theatricality into his movies, forgoing realism in favor of lengthy monologues and rapid dialogue that makes every character into a smarmy, nearly infallible genius. He’s almost as infatuated with corporate and political mechanics as he is with the egos that manipulate them. And the density of his characters’ chatter always requires a nimble pace.
Let’s take a walk through the films of Aaron Sorkin, from worst to best.
9. Charlie Wilson’s War
A tonally messy comedy that falls short of satirical resonance, Charlie Wilson’s War is the final film from esteemed director Mike Nichols. The movie chronicles the origins of American logistical support for the Afghan mujahideen during an extended conflict with the Soviets. At its best, Sorkin’s script explores the fragility of the international political system and the absurdity of the United States’ dominance within it, paying special attention to how politicians and wars can be bought and sold.
Unfortunately, the movie bizarrely wavers between reverence and disgust for American politics, which leaves its actors with the tricky task of balancing earnestness and satire. Each scene has high entertainment value, but the flow of the overall movie feels incredibly inconsistent and disappointingly toothless. It doesn’t help that star Tom Hanks allegedly rejected a much darker, more fitting ending that would have tied the project together thematically. Julia Roberts and Philip Seymour Hoffman costar, with the latter rattling off Sorkin’s dialogue like it’s second nature.
8. The American President
The second collaboration between Sorkin and director Rob Reiner, The American President imagines what would happen if a widowed commander-in-chief pursued romance while running for reelection. The result is in an intermittently intriguing reflection on the intersections between the personal and the political. For better or worse, this film feels like the most stereotypically Sorkinian movie ever made: there’s a political setting, rapid-fire wit, likable characters who are almost perfect at their jobs, lengthy monologues, horrendously over-the-top musical cues, and an odd balance of snark and earnestness. It’s basically a rough draft of an extended West Wing episode with a dash of romantic comedy thrown in.
The American President is completely watchable, thanks primarily to its lighthearted tone and wonderful cast –– Michael Douglas, Annette Bening, and Michael J. Fox all sound amazing as they rattle off indulgent dialogue and lofty speeches. But Sorkin’s screenplay is one of his weakest to date. The conversations here occasionally sound like someone trying and failing to imitate Sorkin’s style — there are so many attempted clever one-liners that many of them fall flat, registering as failed dad jokes instead of pop poetry. And the plot, while charming, is so far removed from actual American politics that it’s difficult to buy into in the first place.
7. Malice
Despite a star-studded cast including Nicole Kidman, Bill Pullman, and Alec Baldwin, Sorkin’s second screenplay is his least-known project, and undoubtedly his most unique work to date. Cowritten with Scott Frank and Jonas McCord, Malice combines elements of the medical drama, erotic thriller, and murder mystery to create an absurdly twist-heavy melodrama. The screenplay features so many heel turns and red herrings that it’s absolutely impossible to guess where this movie is going until the very end.
This is the rare Sorkin film that prioritizes plot over dialogue — there’s only a few theatrical flourishes here and there that indicate the writer’s involvement, including a monologue-heavy deposition scene that’s effectively a warm-up for The Social Network. The story is effortlessly engaging, but it moves in so many different directions that it’s difficult to discern whether it makes any sense at all.
6. Molly’s Game
Sorkin’s directorial debut tells the true story of a professional skier who runs a high-stakes celebrity gambling ring after a career-ending injury. The film takes a heavily explanatory approach to the poker world for maximum accessibility –– Molly Bloom, played by Jessica Chastain, narrates several riveting card games with Sorkin’s signature speed and wit. His directorial voice isn’t particularly distinct or flashy, as he lets his writing do most of the heavy lifting, but he still elicits great performances from his cast –– Chastain excels in the titular role, while Michael Cera leaves a chilling impression as an entitled Hollywood star who may or may not be based on Tobey Maguire.
The majority of Molly’s Game is completely engrossing, as Sorkin builds layers of tension through flashbacks and time jumps. But the film falters when it attempts to develop its central character –– many of the emotional beats are too earnest for the movie’s snarky tone.
5) The Trial of the Chicago 7
Sorkin doesn’t display much growth as a director in his sophomore outing, but The Trial of the Chicago 7 still packs a hefty political punch –– a strength that his films have lacked since his early career. The filmmaker constructs the story, which follows the protests and police brutality outside the 1968 Democratic Convention, in such a way that intentionally parallels our twenty-first century police state. The courtroom theatrics don’t work nearly as well as they do in A Few Good Men, primarily due to a more convoluted story and decidedly less-flashy performances. Instead, Chicago 7 finds more power in the scenes outside of the courthouse, especially in the engrossing sequences where the filmmaker cleverly blends flashbacks with behind-the-scenes strategizing from the defendants.
The film’s progressive characters and themes don’t really fit Sorkin’s political tendencies –– his repeated romanticization of American political systems and norms make him an odd choice to tell this particular story –– but he still manages to pose intriguing questions about divisions within the progressive movement and the best strategy for radical reform. And there are definitely several more factors that are cause for hesitation –– the treatment of the Black Panthers feels like a hesitant afterthought, the final scene is one of the tackiest that Sorkin has ever written, and the cast skews both too old and too British for a fundamentally youthful, American story. But Chicago 7’s timeliness and cleverness makes it a relatively successful piece of political filmmaking despite its flaws.
4. Steve Jobs
This biopic of the titular tech giant is like an Apple product in movie form: it’s slick, streamlined, and widely appealing in its simplicity. Sorkin’s script avoids the cardinal sin of biographical filmmaking –– that is, cramming too much of a person’s life into a two-hour movie –– by narrowing its scope. Steve Jobs presents its subject in three forty-minute chapters that play out in real time, all leading up to critical product launches. The limited timeframe creates tons of tension, as Jobs navigates logistical and interpersonal conflicts mere moments before taking the stage and changing the world.
Sorkin primarily focuses on the cost of greatness, and brilliantly highlights a harsh reality –– the drive that makes people successful in the business world also makes them insufferable on a personal level. The film is far from perfect –– the time constraint makes the integration of Jobs’ familial issues feel absurdly forced, and the hokey final minutes seem like they’re part of a completely different movie –– but Steve Jobs is still a brilliantly entertaining and consistently insightful portrait of a fascinating man.
3. Moneyball
Moneyball has a far more realistic, subdued rhythm than the screenwriter’s other projects, probably because Sorkin didn’t initiate this project –– Schindler’s List scribe Steve Zaillian wrote an earlier version of the screenplay, and also worked on a separate draft of the movie while Sorkin worked on his own. The movie dramatizes the story of Billy Beane, the Oakland A’s’ GM who revolutionized baseball scouting and management.
Beane proves to be the most likable protagonist in Sorkin’s filmography, thanks to Brad Pitt’s incredible performance. In typical Sorkinesque fashion, he’s a quick-witted smartass, but Pitt provides enough emotion and nuance to set himself apart from the screenwriter’s other protagonists. The writing for the character is also more layered than usual –– it’s rare to see the lead in a Sorkin movie doubt himself; in Moneyball, Beane does it repeatedly, perhaps due to Zaillian’s influence or Beane’s actual story. But regardless of its origin, Pitt completely sells the character’s internal conflict with his signature swagger and grace.
2. A Few Good Men
Sorkin trained in theatre in college and started his writing career as a playwright, so it makes sense that his first foray into screenwriting was adapting his own play. Directed by Rob Reiner, A Few Good Men examines military ethics through the lens of a riveting legal battle. Reiner directs a stellar cast (including Tom Cruise, Demi Moore, Jack Nicholson, and Kevin Bacon) to near-perfect performances that make legal jargon more exciting than a shootout. Here, the director exploits Sorkin’s indulgent wit for maximal dramatic effect by arranging his speeches in a calculated rhythm of tension –– people shout over each other and interrupt at perfect intervals.
But A Few Good Men also makes great use of silence. In the midst of long-winded monologues and constant sharp banter, many of the film’s most impactful moments arrive when characters catch their breath and have nothing to say. Glimpses of confusion, hesitance, and reservedness rarely surface in Sorkin’s characters, so when they finally go quiet, it feels very, very important.
1. The Social Network
David Fincher’s Facebook film combines several disparate genres –– legal thriller, college comedy, Shakespearean tragedy –– that all come together for one of the greatest fact-based movies ever made. The screenplay is Sorkin’s best work by a wide margin, as the structure and pacing are practically flawless, and his ridiculously witty dialogue sounds more natural coming from pretentious Ivy Leaguers and slimy entrepreneurs than in any other setting he’s depicted.
Fincher’s direction substantially elevates Sorkin’s material –– while the scribe writes every character as an eloquent genius, the director elicits remarkable performances from his young actors that assures everyone a degree of sympathy. The Social Network parallels Steve Jobs in its exploration of the ties between corporate success and personal failure, but Fincher sets his film apart by achieving something Danny Boyle never could: he makes us feel sorry for his backstabbing bullies despite their perpetual cruelty.
