Drama
Eight Men Out 1988
John Sayles on the 1919 Black Sox; a show of hands put roughly 80% of the room as never having seen it.
The Big Picture · Draft
The Chicago Movie Draft LIVE in Chicago!
July 22, 2025/ 119 min/ Sean Fennessey · Amanda Dobbins · Chris Ryan · Tracy Letts
A live Chicago movie draft from the Steppenwolf Theatre, with playwright and Steppenwolf company member Tracy Letts as the fourth chair. After a Criterion-sponsored trivia round, Sean, Amanda, Chris Ryan, and Letts each fill a six-slot board (Drama, Oscar Nominee, Blockbuster, Action / Horror / Thriller, Comedy, Wildcard) while arguing over what counts as a Chicago movie. The room votes; Amanda wins.
24 films across 1 segment.
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 teams drafting Chicago movies
Chris Ryan
Oscar Nominee
Primal Fear 1996
Gregory Hoblit; Edward Norton's Oscar-nominated breakout, with John Mahoney as a Steppenwolf company member.
Blockbuster
The Dark Knight 2008
Ryan's ruling: Begins is Mongolia, Dark Knight is Chicago, Rises is Pittsburgh.
Action / Horror / Thriller
Thief 1981
First overall pick. Michael Mann's safecracker movie with James Caan; his favorite Chicago film, a Criterion title.
Comedy
The Sting 1973
George Roy Hill, Newman and Redford; Best Picture winner. Ryan prefers it to Butch Cassidy and the Sundance Kid.
Wildcard
Glengarry Glen Ross 1992
Mamet; drafted in honor of Letts, who has twice played Williamson on the Steppenwolf stage.
Sean Fennessey
Drama
Risky Business 1983
Tangerine Dream score; the category-fraud pick the whole table contested as a comedy.
Oscar Nominee
The Fugitive 1993
Andrew Davis; Tommy Lee Jones won Supporting Actor. Argued as the most Chicago-per-minute movie there is.
Blockbuster
The Color of Money 1986
Scorsese; Newman and Cruise. 'Spiritually Chicago' before it moves on to Atlantic City.
Action / Horror / Thriller
House of Games 1987
Mamet's con-man movie with Joe Mantegna and Ricky Jay; a film Sean's father showed him at ten.
Wildcard
Transformers: Dark of the Moon 2011
Bay's moon-landing / JFK conspiracy entry; the joke pick that got its own printed placard.
Amanda Dobbins
Drama
A League of Their Own 1992
Penny Marshall; Amanda insists on drama, citing the war telegram and the Cooperstown coda.
Blockbuster
My Best Friend's Wedding 1997
Her most-watched Julia Roberts rom-com and a top-five in the genre for her; owned it on VHS.
Action / Horror / Thriller
Widows 2018
Steve McQueen's Chicago-politics heist; the long Colin Farrell car shot from the poorest wards to his own block.
Comedy
Ferris Bueller's Day Off 1986
Her favorite John Hughes movie, watched a thousand times on VHS.
Wildcard
While You Were Sleeping 1995
Sandra Bullock on the L; occasion for Amanda's unprompted full-plot recap.
Tracy Letts
Drama
Medium Cool 1969
Haskell Wexler shot fiction into the real 1968 Chicago riots: 'Look out, Haskell, it's real.' The least-seen pick of the night.
Oscar Nominee
Hoop Dreams 1994
Steve James; Letts's No. 1 pick and, to him, the best sports movie ever made.
Blockbuster
The Untouchables 1987
De Palma, Morricone score; Letts notes it cast no Chicago actors except improv guru Del Close.
Action / Horror / Thriller
Henry: Portrait of a Serial Killer 1986
John McNaughton; Michael Rooker on Lower Wacker, filmed as Letts arrived in town.
Comedy
The Blues Brothers 1980
Belushi and Aykroyd, Aretha Franklin, and the record-setting police-car pileup.
Wildcard
Love Jones 1997
Theodore Witcher's only feature; Larenz Tate and Nia Long, a Criterion edition.
On the board, undrafted honorable mentions
My BodyguardOrdinary PeopleCooley HighThe Breakfast ClubThe Front PageThe Man with the Golden ArmPlanes, Trains and AutomobilesAbout Last NightMidnight RunJudas and the Black MessiahBackdraftI, RobotHigh FidelityBridesmaidsFlatlinersSinnersBarbershopRunning ScaredHis New JobBlackhatThe Accountant
Also mentioned raised along the way
In the trivia round Ne Zha 2Ne ZhaJurassic World RebirthManhunterChicagoThe Great ZiegfeldBlues Brothers 2000CandymanFinal Destination BloodlinesRookie of the YearStraight Talk9 to 5
Also mentioned His Girl FridayButch Cassidy and the Sundance KidSleepless in SeattleFallenTank GirlWild ThingsMad Dog and GloryThe Texas Chain Saw MassacreDressed to KillField of DreamsNotting HillPretty WomanApollo 13Game NightApocalypse NowBreakfast at Tiffany'sThe MatrixMission: ImpossibleSoul FoodPorky'sThe HustlerBatman BeginsThe Dark Knight RisesOppenheimerMementoCollateralNorth by NorthwestScarfaceCompulsionMean GirlsWayne's World 2
Not films filtered out: TV, games, ads
Plays August: Osage CountyWho's Afraid of Virginia Woolf?True WestBalm in GileadThe Glass MenageriePicasso at the Lapin Agile
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