Aaron Sorkin – Ranked

Aaron Sorkin has been one of the biggest names in TV and film writing since the early 1990’s. Throughout his career he has captivated audiences with his distinct, innovative, and dialogue-heavy writing style. Both his television work, which includes shows like The West Wing, Sports Night, and The Newsroom, and his films, including The Social Network, A Few Good Men, Charlie Wilson’s War, and The American President, have garnered praise from fans and critics alike. In this specific piece though, I am solely going to be taking a look at his award-winning and influential film career.

Any analysis of Sorkin’s career starts and end with a discussion revolving around dialogue. Sorkin’s fast paced, witty dialogue has been his trademark since he made his Hollywood debut with A Few Good Men. Perhaps more than any screenwriter in history, Sorkin has the ability to keep the audience engaged in literally whatever discussion is being had on screen. I don’t think there is any screenwriter better at writing banter than Sorkin. I don’t find this ability to be a gratuitous one either because Sorkin’s dialogue doesn’t just sound great, it is often essential to understanding his characters and the story being told. In a Sorkin script, so much can be taken away from moments that may appear, on the surface, to just be two or more characters engaging in small talk. It is in these sharp and swift exchanges though, that the audience learns about the characters, the tone of the film, and the conflict, without ever having any of these things explicitly explained to them. In other words, Sorkin grabs your attention with his dialogue, and through that dialogue he gives you the information needed to fully understand the story, without you ever noticing.

Sorkin’s films have taken an in-depth look at a variety of different worlds, such as politics, law, tech, and professional sports, amongst others. One thing I appreciate about his writing style is that he never dumbs down the language used in these fields for the sake of the audience. Sorkin has an innate ability to never make the audience feel uninformed, even when he includes jargon in his scripts that they may not be familiar with. The meaning always comes across, even if the exact definitions of the terms may not be known by everyone watching. Perhaps the greatest thing about Sorkin’s dialogue, from an aesthetic standpoint, is just how musical he is able to make it sound. There is a rhythmic quality to Sorkin’s scripts that make both his television and film work even more entertaining. Seemingly, he is writing music as much as he is writing dialogue while working on a script. However, it is that rhythmic quality that makes me feel a little unsure when people laud Sorkin’s dialogue for being “so realistic.” I’d argue that Sorkin’s dialogue is realistic in that it is an example of how we all wish we sounded, rather than how we actually sound. More specifically, Sorkin’s dialogue would actually be “realistic” if we all lived in a world where we could think of the right retort in the moment, rather than three hours after the exchange took place. This isn’t a criticism though, Sorkin’s scripts gives us that sensation of having the right thing to say in the right moment, which I think is why we love them. I don’t think being completely realistic should necessarily be the goal in screenwriting. Art, including television and film, should be a representation of real life, but still needs to be interesting enough to make us want to watch it, and escape from the dullness of our actual real lives. It’s clear to me that Sorkin understands this idea.

Dialogue is not the only thing that makes Sorkin’s scripts special. He is also incredibly talented when it comes to creating and developing characters. Whether they are completely fictional or real people, he has written some of the most memorable characters of the last 30 years or so. What makes Sorkin’s character development so excellent is that he knows the best approach is to show us who a character is and what they want, rather than tell us. As I mentioned earlier, Sorkin is not the kind of screenwriter who spends a lot of time explaining things to the audience. Instead of simply telling the audience what a character needs or wants, and what obstacles stand in their way, he shows us that character going for what they want while facing different obstacles along the way. Throughout his career, Sorkin has written stories that primarily focus on one central character, as well as stories driven by an ensemble. All of his films contain fully fleshed out and realized characters though. Every character in a Sorkin script is there for a reason, they serve a purpose to the overall story in one way or another. Sometimes when you watch a film, you can tell that the screenwriter didn’t give the proper time or attention to all of the characters in their script. Conversely, Sorkin always seems to be in control of every character he writes. It is important to also mention the incredibly talented group of actors that have worked on Sorkin-penned films over the years. Sorkin does indeed create the characters, but it is up to the actor to then bring that character to life. Throughout his career, Sorkin has gotten lucky with casting quite often, as the studio and the director making his scripts into films continuously find the right actor to play the right part. One cannot think about Sorkin’s film career without also thinking of the great performances from actors like Tom Cruise, Jack Nicholson, Michael Douglas, Brad Pitt, Jesse Eisenberg, and Jessica Chastain.

I briefly mentioned that Sorkin has written films about real people in his career. In recent years, this seems to be something he has grown more and more interested in doing. Since 2007, he has written five films based on true stories. Occasionally, these films, and Sorkin himself, will be criticized for not accurately portraying the real-life events of the story being told. I especially remember this being a controversy when Steve Jobs was released in 2015. I have slightly mixed feelings on this issue. While I understand why people close to these stories may be upset that they are not being depicted 100% accurately, I also appreciate the fact that filmmakers do need to be allowed to take some artistic liberties while telling a story. The fact of the matter is, every single film that is “based on a true story” is not giving the audience a fully precise representation of the real-life story. Sorkin tells true stories, but he also understands what makes a film compelling. He may exaggerate somethings, change language, or focus heavily on conflicts that were ultimately not that substantial in real-life, but he does so for the sake of storytelling.

His films not being 100% accurate is not the only criticism that Sorkin has received throughout his career. At times, people have criticized some of his work for basically being “too Sorkin-ey.” This means his distinct style actually overpowers the final product, and this perceived overindulgence of his own style has led some to dismiss a handful of his works throughout his career. I can understand this criticism, and at times I may agree with it myself, however, this criticism also feels unfair on certain occasions. I’d argue that, because we are all incredibly aware of what a Sorkin project looks like and what his trademarks are, it’s almost seen as “cooler” now to mock or criticize his style, than to genuinely appreciate it. Also, not only has his past greatness led to extremely high expectations for every new project of his, but people pay attention to the script more when Sorkin’s name is attached. That can lead to far more nitpicking and scrutiny of his scripts than most normal movie script get.

At the end of the day, Sorkin’s film career has been a mostly great one so far, highlighted by some decade-defining films. Even if he were to never type another word, he has already established his legacy as one of the greatest screenwriters of all time.

Now, without further ado let’s unnecessarily take a bunch of meaningful works of art from a brilliant filmmaker and pit them against each other for no apparent reason.

8. Malice (1993)

“Welcome to the game.”

Malice is probably Sorkin’s least known film, and widely regarded as his worst from those who are familiar with it. The film can be best described as a thriller, which is a departure for Sorkin. This was his second film, released after the incredible success of A Few Good Men, which came out just one year earlier. It is not surprising that Sorkin has not returned to the style and tone of Malice since 1993 though. The story itself centers on a seemingly normal and happy married couple whose lives are upended when a successful, charming, and powerful doctor comes into the picture. The doctor, Jed, is played by Alec Baldwin and the married couple, Tracy and Andy, are played by Nicole Kidman and Bill Pullman. My problems with the film do not lie in the performances, which I find to be perfectly fine. The story is without a doubt Sorkin’s messiest though. There are some holes in the plot, as well as storylines that feel ultimately unnecessary. Also, Malice‘s director, Harold Becker, is undoubtably the least-acclaimed director Sorkin has worked with throughout his career, which clearly had an effect on the overall quality of this film, relative to Sorkin’s others. Unlike A Few Good Men, which has managed to age incredibly well, Malice feels incredibly dated when watched in 2020. This is certainly not a completely terrible film though. In fact, I’d argue that despite its flaws, it’s pretty entertaining. It is still a Sorkin script led by three great actors, and there is enough mystery and intrigue packed into the story to keep the viewer engaged throughout, even if some of the twists and turns are fairly predictable. I certainly wouldn’t recommend this film as a starting point to someone unfamiliar with Sorkin’s work, but if you are familiar with his work, you’ve never seen Malice, and the story intrigues you, then I think it is, at the very least, worthy of a watch.

7. Molly’s Game (2017)

“You know what makes you feel okay about losing? Winning.”

Sorkin’s directorial debut, Molly’s Game, is also his most recent film. The film was released in 2017 to mostly mixed reviews. It is based on a true story, and chronicles the life of Molly Bloom, an Olympic level skier who went on to run some of the most exclusive high-stakes poker games in the world. The story, as well as the performance of Jessica Chastain who stars in the titular role, are certainly the two greatest aspects of this film. Like I previously stated, this was the first time Sorkin got behind the camera and directed one of his own scripts. I cannot say that Sorkin did a bad job as director, but I will say that Molly’s Game does seem to be missing some of the magic that Sorkin’s other works possess. The film as a whole just feels a bit more unimaginative and less polished than previous Sorkin films, which were obviously handled by more experienced directors. The script for this film is very strong. However, there is an abundant use of narration included in this film, which I found to be a very strange choice for a screenwriter most known for his dialogue. The reliance on Jessica Chastain’s voiceover throughout the film is another reason Molly’s Game just feels a little bit less-than for me, when I compare it to Sorkin’s other works. One of the best things this film has going for it though is that it is undeniably watchable. To me, this is the case for all of Sorkin’s works. Even the lesser films in his catalogue are going to be fairly entertaining and utterly watchable because of his style. Molly’s Game is no exception. It certainly isn’t Sorkin’s best, and his directing skills may not be as great as his writing skills, but the performance of Chastain and the strength of this script still keep you entertained throughout.

6. Charlie Wilson’s War (2007)

“You know you’ve reached rock bottom when you’re told you have character flaws by a man who hanged his predecessor in a military coup.”

This was the first film released after Sorkin’s television run of Sports Night, The West Wing, and Studio 60 on the Sunset Strip ended. In fact, when Charlie Wilson’s War was released in 2007, it had been 12 years since the release of the previous Sorkin film, The American President. Charlie Wilson’s War was also the final film in Mike Nichols’ legendary career. I mentioned earlier that Sorkin’s film have possessed some great actors over the years, but an argument can certainly be made that this film has more talent surrounding it than any other. When you have names like Tom Hanks, Julia Roberts, Amy Adams, and the late great Philip Seymour Hoffman attached to an Aaron Sorkin script being directed by Mike Nichols, it is virtually impossible for a bad film to be made. And, despite its relatively low spot on this list, I absolutely wouldn’t call Charlie Wilson’s War a bad film by any means. In fact, this may be Sorkin’s most comedic and most purely-fun film of all time. One might not be able to tell that from the plot description though, because this film tells the true story of Texas congressman Charlie Wilson’s covert efforts to assist rebels in Afghanistan during their war with the Soviet Union. The script is extraordinary, the performances are memorable, and the directing is excellent as well. Of course, Sorkin has dipped into the world of politics many times throughout his career, but I find Charlie Wilson’s War to be one of the most brutally honest looks into that field that Sorkin has ever given us. There is a moment towards the end of this film in which Sorkin has Hoffman’s character relay this idea that even though an event may seem good or bad in the moment, no one knows what the future will bring or what the ultimate effect of that event will be. The final moments of this film capture that idea and that sensation so impressively well, which sheds a light on how our political system works in a lot of ways. The reason this film ranks a little lower on my list is because, despite being entertaining, it lacks some of the emotion that Sorkin’s other films possess.

5. The American President (1995)

“You fight the fights you can win? You fight the fights that need fighting!”

The American President was the third Sorkin film ever released and, in some ways, led to one of the best television shows of the last 20 years, The West Wing. Sorkin has stated in interviews that the initial idea for The West Wing came from a friend of his who told him the idea after seeing a poster for The American President in Sorkin’s house. It is not hard to see how this film inspired that initial idea, seeing as many of its main character are made up by the President of the United States and his senior staff. The actual plot of this film is far different from The West Wing though. The American President tells the story of a widowed U.S. President, played by Michael Douglas, falling in love with a lobbyist, played by Annette Bening. Both Douglas and Bening give great performances in this film, which is crucial to its success because a lot of that success relies on the believable, romantic chemistry between the two. The film is also rounded out by some very solid supporting performances, given by actors such as Martin Sheen, Michael J. Fox, Anna Deavere Smith, and David Paymer, amongst others. Many of Sorkin’s films have romantic elements included in them, but The American President is his definitive rom-com, and it’s a damn entertaining rom-com as well. Sorkin’s writing style fits perfectly with this genre, and Rob Reiner, who had directed Sorkin’s A Few Good Men three years prior to this film, was the perfect director to take on this project as well. The story is not overly-complex, which, in many ways, leads to the film’s overall success. It is clear that Sorkin wasn’t trying to do too much or say too much with this script, instead, he simply wanted to make an enjoyable and fun movie, and he ultimately accomplished that goal. This is sneakily one of the best rom-coms to come out of the 90’s, and I would recommend it to anyone interested in that genre, or interested in Sorkin’s work in general.

4. Steve Jobs (2015)

“I don’t want people to dislike me. I’m indifferent to whether they dislike me.”

Sorkin’s 2015 film about the controversial Apple co-founder is the number four film on my list. Some may consider this placement too high, but I have been a defender of Steve Jobs since it was released five years ago. Perhaps the most notable thing about this film, besides from Sorkin’s involvement with it, is the way in which it is told. Sorkin, and director Danny Boyle, do not approach this story in a conventional manner. Instead, they choose to look at the life of Jobs by taking a detailed look at three separate product launches throughout his career. I found this unorthodox approach to be wildly effective for a variety of reasons. First, this structure allows the audience to see how Jobs evolved throughout the course of his career. Second, Sorkin and Boyle examine Jobs from a multitude of different angles. The audience gets to see how he interacted with current colleagues, former colleagues, and his family, as well as how he viewed himself, the work he did, and American consumers. Lastly, Sorkin’s unique story structure makes this film feel different from the hoards of biopics released every year that all follow a similar formula. I really appreciate Sorkin’s attempt to do something new with this format, and find the result to be incredibly compelling. In terms of dialogue, this film contains some of the best arguments Sorkin has ever written in film or in television. From the opening scene, the audience understands that, maybe even more so than any of Sorkin’s other films, Steve Jobs is going to be carried by dialogue. A film as dialogue-driven as this one needs incredible acting performances to be successful, and Michael Fassbender, Kate Winslet, Seth Rogen, Jeff Daniels, Michael Stuhlberg, and Katherine Waterston are all tremendous in their respective roles. I would recommending rewatching this film if you haven’t seen it since its initial release because I think it is truly some of the best writing work of Sorkin’s career.

3. Moneyball (2011)

“How can you not be romantic about baseball?”

In my opinion, this past decade has clearly been Sorkin’s best, from a film perspective. In fact, Moneyball is the second of three 2010’s films that will ultimately make up 75% of my top four Sorkin films. Initially, I thought about placing this film lower on my list since Sorkin was brought into this project late to revise and rewrite a script that, at that point, already had undergone two previous versions. Also, this is the only film in Sorkin’s career in which he shares screenwriting credit with another writer. Steven Zaillian, an incredibly acclaimed screenwriter in his own right, apparently wrote the second version of this script and is credited as the co-writer. Regardless of all that though, I couldn’t deny my love for this film, and knew I had to find a place for it near the top of this list. This film is, of course, based on the Michael Lewis book of the same name, which chronicled how Oakland A’s general manager, Billy Beane, transformed his team in the early 2000’s and changed baseball forever. As with all of the greatest sports films in history, Moneyball is so effective because it’s not really about sports. It uses the backdrop of sports to tell a moving story about the human condition. One cannot write about this film without mentioning the Oscar-nominated performance given by Brad Pitt. If someone were to ask the question, “what makes a movie star, a movie star?” all you would have to do is show them Pitt’s performance in this film. Pitt absolutely commands the screen in every scene he is in. His performance is exceptionally effortless, yet unbelievably effective. I must mention that Jonah Hill was also nominated for his outstanding work in this film too, and Philip Seymour Hoffman, Robin Wright, Chris Pratt, and Ken Medlock all give great supporting performances as well. This is Pitt’s movie from start to finish though. In fact, the only thing that maybe shines as much as Pitt does, is the script. Moneyball manages to be funny, inspiring, heartwarming, and heartbreaking all at the same time and because of that, it is my number three Sorkin film.

2. A Few Good Men (1992)

“You can’t handle the truth!”

Sometimes things just happen to go your way in Hollywood. For example, sometimes you adapt your own play into your first screenplay, and you end up getting Tom Cruise and Jack Nicholson to star in it. That is precisely what happened to Aaron Sorkin in the early 1990’s with A Few Good Men. This was Sorkin’s debut into the filmmaking world, and it is hard to think of a better way for him to announce himself. This film is deserving of the iconic nature it possesses due to its most famous exchange. It may be that famous exchange between Tom Cruise and Jack Nicholson that sticks out most in people’s heads when they think of A Few Good Men, but this film is so much more than just one great scene. As a whole, it is an incredibly well-written and compelling drama backed by some powerhouse performances. It also happens to be one of the most rewatchable films of all time. One of the most impressive things about this film is the fact that it came out nearly 30 years ago, yet doesn’t feel dated at all. Someone who has never seen this film could watch it today and be just as enthralled as the people who saw it in 1992 were. A large reason for that is the script. As I previously stated, this was obviously Sorkin’s first script, and I honestly wouldn’t have a problem if someone praised it as his best. This film is practically all dialogue, but the intensity of that dialogue almost makes it feel like an action movie, especially during that final courtroom scene I was mentioning earlier. Sorkin’s ability to pair emotionally fueled characters with the right lines of dialogue is second to none, and this film is a great example of that. It has one of the most memorable film quotes of all time, possibly the best Tom Cruise performance of his career, and one of the greatest supporting performances in the history of film … which just goes to show you how good of a film my number one Sorkin movie of all time is.

1. The Social Network (2010)

“We lived on farms, then we lived in cities, and now we’re going to live on the internet.”

There is quite simply no greater Sorkin-penned movie than 2010’s The Social Network. Towards the end of 2019, many people gave this film the title of “the greatest film of the decade,” and it is not hard to see why. Not only is Sorkin’s script incredible, but this film has one thing that no other Aaron Sorkin film has, which is David Fincher. This film having Fincher behind the camera elevates it to another level entirely. There is a simple story that illustrates Fincher’s ability to get the most out of Sorkin’s dialogue, which is when Jesse Eisenberg and Rooney Mara were filming the opening scene of The Social Network, he made them do 99 takes. He did this not because they were giving bad performances, but because he wanted them to get comfortable with the language and the rhythm of Sorkin’s script. Another example of Fincher elevating Sorkin’s script is the totality of the performance given by Eisenberg. Throughout his career, Sorkin has had Tom Cruise, Tom Hanks, Jack Nicholson, Amy Adams, Julia Roberts, Michael Fassbender, Philip Seymour Hoffman, Brad Pitt, Nicole Kidman, Michael Douglas, and Annette Bening act out his scripts, but I would still argue that the number one performance given in any Sorkin film is Eisenberg’s performance in this film. I give a lot of this credit to Fincher because, although Eisenberg is a talented actor in his own right, I think it was Fincher’s direction that got him to do such a stellar job with Sorkin’s impeccably written script. Eisenberg isn’t the only one who gives a worthwhile performance in this film either, Andrew Garfield, Armie Hammer, and Justin Timberlake all probably give the best performances of their entire career in this film as well. Moreover, this is without a doubt Sorkin’s most emotionally effective film. Similar to Moneyball, he uses the seemingly inconsequential true story behind The Social Network to make one of the most gripping, interesting, and moving films of the decade. This is a film that will live on long past the decade it was released in though. It will be remembered as a classic, as well as the best cinematic work of Sorkin’s career.