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Aaron Sorkin Top 5s and ‘The Trial of the Chicago 7’

October 16, 2020/ 116 min/ Sean Fennessey · Amanda Dobbins

An Aaron Sorkin special: Sean Fennessey and Amanda Dobbins walk through the writer-director's signatures, trade top-five Sorkin lists, and review 'The Trial of the Chicago 7,' out this weekend on Netflix.

12 films across 4 segments.

AI-generated This episode was transcribed and analyzed with AI models. The matches aren't perfect — expect the occasional misheard title or a link to the wrong film.

The Sorkin Signaturescareer overview

Molly's Game poster

Molly's Game 2017

Sorkin's 2017 directorial debut, the underground-poker drama with Jessica Chastain as Molly Bloom. The hosts keep coming back to the Kevin Costner father-daughter park-bench scene (Amanda thinks it's the best part, Sean thinks there's no reason for it to be in the movie) as a case study in Sorkin's father-of-daughters crutch.

Charlie Wilson's War poster

Charlie Wilson's War 2007

Cited as one of Sorkin's overtly political documents and part of the mid-career pivot from invention to real events. Also where the recurring 'I'm never sick at sea' Gilbert and Sullivan line turns up again.

Malice poster

Malice 1993

Brought up for Alec Baldwin's 'I am God' monologue, which Sean rates as the only Sorkin kicker rivaling 'I am the president' from 'The American President.'

Amanda's Top Five Sorkinranked by Sorkin-ness; her No. 1, 'The West Wing,' and other TV are listed under Not films

A Few Good Men poster

A Few Good Men 1992

No. 2. Her most-seen movie, partly a function of 90s cable, and the broadest-appeal Sorkin, carried by the biggest movie-star performances: Tom Cruise, Jack Nicholson, Demi Moore, Kevin Bacon.

The Social Network poster

The Social Network 2010

No. 3. Shared with Sean; both called it the movie of the 2010s. Amanda singles out the Dakota Johnson 'what was your latest preneur?' throwaway and the ink-not-pencil precision of the writing.

The American President poster

The American President 1995

No. 4. A formative movie she watched with her dad and owned on VHS; a Clinton-era liberal fantasy and a test run for 'The West Wing,' down to Martin Sheen getting promoted from chief of staff to president.

Moneyball poster

Moneyball 2011

No. 5. She ranks it low only because she's ranking by Sorkin-ness, not greatness: otherwise 'one of the greatest movies ever made.' Timed her rewatch to the Braves' playoff run.

Sean's Top Five Sorkinranked by entertainment value; his No. 4, 'Sports Night,' is TV and listed under Not films

A Few Good Men poster

A Few Good Men 1992

No. 1. A conventional military courtroom drama lifted into 'the conversation for the most rewatched movie of my lifetime' by Sorkin's script, and by Cruise and Nicholson.

The Social Network poster

The Social Network 2010

No. 2. His pick for best movie of the last decade; possibly Sorkin's best script, period. The Sorkin-plus-Fincher pairing where the sum is greater than the parts.

Moneyball poster

Moneyball 2011

No. 3. Written first for Soderbergh, directed by Bennett Miller. Sean loves how Pitt and Hill do Sorkin 'slow as molasses,' but still wishes for the darker cut-glass Soderbergh version.

Steve Jobs poster

Steve Jobs 2015

No. 5. Sean's most passionate pick: 'immensely underrated.' A three-act opera directed by Danny Boyle, with what he calls the best Michael Fassbender performance and a robbed Seth Rogen as Wozniak. Read as a spiritual sequel to 'The Social Network.'

‘The Trial of the Chicago 7’spoilers; new on Netflix

The Trial of the Chicago 7 poster

The Trial of the Chicago 7 2020

Sorkin's second feature as director, about the 1969 conspiracy trial of eight anti-war activists charged over the 1968 Democratic National Convention protests. Sacha Baron Cohen as Abbie Hoffman, Eddie Redmayne as Tom Hayden, Yahya Abdul-Mateen II as Bobby Seale, Jeremy Strong as Jerry Rubin, Mark Rylance as William Kunstler, Frank Langella as Judge Hoffman, Joseph Gordon-Levitt as prosecutor Richard Schultz, with a Michael Keaton cameo as Ramsey Clark. Both hosts liked it and neither put it in their top five. Sean calls it the 'peak Sorkin' movie but faults it as a filmmaker's work (the talk scenes are great, the action and protest scenes aren't sharp enough) and is troubled that Sorkin sides with Hayden's incremental protest over Hoffman's cultural revolution. Amanda finds the closing reading of the war dead genuinely moving but feels the smallness of the slice Sorkin chose. Pegged as a heavy Oscar contender against 'Mank' and 'Nomadland.'

Also mentioned raised along the way

Other tellings of the Chicago 7 story Medium CoolPunishment ParkBananasChicago 10

In passing Last Action HeroInglourious BasterdsMoonlightPulp FictionZodiacW.JFKNetworkThe Wizard of OzThe GodfatherGoodfellasRules of EngagementThe Caine MutinyHillbilly ElegyMankNomadlandBorat Subsequent MoviefilmFantastic Beasts and Where to Find ThemThe Theory of EverythingThe Devil Wears Prada

Not films filtered out: TV, games, ads

TV The West Wing (Amanda's No. 1 Sorkin)Sports Night (Sean's No. 4 Sorkin)Studio 60 on the Sunset StripThe NewsroomGilmore GirlsSuccessionConspiracy: The Trial of the Chicago 8

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