Aaron Sorkins 10 Best Characters Ranked

Aaron Sorkin’s 10 Best Characters, Ranked

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Oscar and Emmy nominees abound, big-name Hollywood stars aplenty, these are the characters who have leaped farthest from Sorkin’s pages.

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Aaron Sorkins 10 Best Characters Ranked

Aaron Sorkin is one of the most exciting screenwriters and directors in Hollywood. He has worked in political thrillers, sports stories, and military escapades. What’s most notably remarkable about his work is that much of what you see on screen is people talking. Forget explosions, magic, and sex, when it comes to Sorkin, people talking is more than enough entertainment.

This list celebrates the very best of those people. Often within ensemble casts, these individuals – some based on real-life figures, some creations of Sorkin’s mind – stand out in their immediate wit and eventual depth. Oscar and Emmy nominees abound, big-name Hollywood stars aplenty, these are the characters who have leaped farthest from Sorkin’s pages.

10 Bonnie Bach (Charlie Wilson’s War)

Aaron Sorkins 10 Best Characters Ranked

Charlie Wilson’s War is a talent-rich political intrigue story that was seemingly forged in Oscar gold. Tom Hanks plays a cavalier Congressman, Philip Seymour Hoffman plays an eccentric CIA agent, and Julia Roberts plays a powerful socialite. Phew!

Beating them all to this number ten spot is Amy Adams’, Bonnie Bach. With more screen-time than Hoffman and Roberts, she is the unifying presence in the complex narrative and the emotional counterbalance to three strong personalities. Adams has been nominated for five Oscars since this performance.

9 John Scully (Steve Jobs)

Aaron Sorkins 10 Best Characters Ranked

Aaron Sorkin-Jeff Daniels is the artistic partnership that has not yet hit its peak. The short-lived The Newsroom had lots of potential. Sorkin’s stage adaption of To Kill a Mockingbird, starring Daniels as Atticus Finch, met rave reviews, but obviously not a mass audience.

For a vision of what the inevitable future masterpiece between the two might look like, revisit Steve Jobs. Leaning on Michael Fassbender’s titular character more than Daniels, the latter entertains with pure dialogue and achieves characterization extremely efficiently.

8 Dana Whitaker (Sports Night)

Aaron Sorkins 10 Best Characters Ranked

Real Sorkin-heads will be familiar with Sports Night, the scribes first foray into television that ran from 1998-2000 and led directly into The West Wing. It has an extremely similar energy to the political drama, just within a television studio (something Sorkin would attempt to return to after The West Wing with Studio 60 on the Sunset Strip.

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Felicity Huffman is magnificent as fictional executive producer Dana Whitaker. Despite the “boys club” environment, she takes the lead on her fair share of drama, scandal, and laughs too.

7 Josh Lyman (The West Wing)

Aaron Sorkins 10 Best Characters Ranked

It is difficult to overstate the charm and magic of The West Wing but to put it one way, it made Bradley Whitford cool. With the non-sexy title “Deputy Chief of Staff”, Whitford, like Lyman, puts on a dazzling performance of witty zingers and top-tier decision-making, often without breaking a sweat. (For reference, the current Deputy Chief of Staff is John Fleming, who you’ve never heard of.)

To this day, one of the trademarks of Aaron Sorkin’s work is the “walk-and-talk” scene. Lyman may very well be the greatest Sorkin walk-and-talker of all-time.

6 Peter Brand (Moneyball)

Aaron Sorkins 10 Best Characters Ranked

After Brad Pitt’s career-capping Oscar win this past year for Once Upon a Time…in Hollywood, many film fans revisited other notable roles of his and rediscovered appreciation for characters like his Billy Beane in Moneyball. It should not be forgotten, however, that the unexpected standout from that Aaron Sorkin/Michael Lewis/Bennett Miler project was Jonah Hill!

Of Superbad fame, Hill had not played anywhere near the drama space when he met the Sorkin character Peter Brand. Thus the clamor when his neutral-neutral goofiness served a particularly realistic and emotional purpose as a juxtaposition to Pitt’s big-timer down-and-out portrayal.

5 Molly Bloom (Molly’s Game)

Aaron Sorkins 10 Best Characters Ranked

The story of the life of Molly Bloom is epic, fascinating, and not to be covered here. One chapter of it was covered in the Oscar-buzzy 2017 film Molly’s Game. In real life and the film, Bloom attracted high-profile celebrities and wealthy folks to a regular secret high-stakes poker game, before it all went up in legal smoke.

On male-dominated stories like that of The White House and more recently The Trial of the Chicago 7, Sorkin has built much of his career. Here, as Bloom, Jennifer Chastain shows that women in a Sorkin script can be just as cutting, backstabbing, and gleeful all the livelong way.

4 The Winklevoss Twins (The Social Network)

Aaron Sorkins 10 Best Characters Ranked

Currently making noise on Netflix is the Hitchcock remake Rebecca, starring Armie Hammer. Since his breakout double-role here in The Social Network, the impossibly handsome actor has been ubiquitous in Hollywood as the malignant white male.

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How appropriate that that career be launched from the halls of Ivy League fraternity houses and the tables of corporate law firms. The Winklevoss Twins are vicious antagonists to the antihero Mark Zuckerberg. While in the latter’s mind it’s a Revenge of the Nerds scenario, all viewers see is the totality of the privileged.

3 Col. Nathan R. Jessup (A Few Good Men)

Aaron Sorkins 10 Best Characters Ranked

One of the greatest actors of all time, Jack Nicholson has never been above a character role or genre pieces, even late into his career. In fact, he elevates these jobs, often to all-time classics (See Batman, The Shining, Terms of Endearment…)

As a frumpy and callous defense witness up against a prime-career Tom Cruise, Nicholson once again gets eyeballs (and even sympathies) on his side scene after scene. In this role, Nicholson scored an Oscar nomination and one of the most famous movie lines of all time.

2 Mark Zuckerberg (The Social Network)

Aaron Sorkins 10 Best Characters Ranked

The Social Network is widely considered one of the best films of the 21st century thus far, in part due to its apparent prescience. Casting celebrity tech wiz Mark Zuckerberg as a Shakespearean villain might have read to 2010s audiences as an attempt to make just about anything into a thriller.

To viewers today, who have seen Zuckerberg testify in Congress numerous times and be indicated at the core of some of our nation’s most novel macro-issues, Jesse Eisenberg’s cold, sympathetic portrayal of a man who wanted more power and earned it is chilling contemporary canon.

1 Josiah “Jed” Bartlett (The West Wing)

President Bartlett is the epitome of The West Wing’s rosy view of the political world. The man does not have a nefarious, self-serving, or dishonest bone in his body. He is instead something of a savant dork (capable of quoting ancient literature or inane anthropological factoids off-hand) with the ability to make anyone in any room smile.

Through (Spoiler Alert) two terms in office, how does he fare in the storied oval office? The West Wing version of the American economy thrives, numerous complex combat situations are navigated, and only a few paltry scandals emerge. Bartlett would give himself a B+.

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