The Big Picture: The Chicago Movie Draft LIVE in Chicago! Episode Release Date: July 22, 2025

Introduction In this special live episode of The Big Picture hosted by Sean Fennessey and Amanda Dobbins, the Ringer team delves into the vibrant world of Chicago cinema. The episode, titled "The Chicago Movie Draft LIVE in Chicago!", features a dynamic conversation among regular hosts and guests, including Chris Ryan and Chicago theater legend Tracy Letts. The main event centers around drafting the best Chicago movies across various categories, intertwined with engaging trivia sponsored by the Criterion Collection.

Trivia Challenge The episode kicks off with a lively trivia segment, sponsored by the Criterion Collection and the Criterion Channel. Sean emphasizes the importance of a fair and respectful trivia process:

Sean Fennessey [02:25]: "If you yell out the answer, no more trivia. If you start saying things that are not the right answer just to get attention for yourself, no more trivia."

Amanda adds a humorous caution:

Amanda Dobbins [01:36]: "If people start blurting out answers, there will be no more Trivia."

The trivia questions ranged from identifying the highest-grossing movie of 2025 to specific details about classic Chicago-based films like Jurassic World: Rebirth and True West. Audience participation was encouraged, with prizes linked to Criterion’s curated selection of Chicago-rooted films.

One standout moment occurs when Chris Ryan correctly identifies Nezha 2 as the highest-grossing movie:

Chris Ryan [04:07]: "Nejatu."

Drafting the Movies: Categories and Picks Following the trivia, the focus shifts to the main event: drafting Chicago movies across six categories—Drama, Oscar Nominee, Blockbuster, Action/Horror/Thriller, Comedy, and Wild Card. Each participant selects their top choices, providing insights and personal anecdotes about each film.

1. Drama

   • Sean Fennessey: Picks Risky Business.

     Sean Fennessy [74:54]: "One of the most dramatic films ever made, Risky Business."

   • Chris Ryan: Chooses Eight Men Out, highlighting its portrayal of the Black Sox scandal.

     Chris Ryan [76:10]: "An incredibly dense and well-written piece of filmmaking."

   • Amanda Dobbins: Selects A League of Their Own, appreciating its heartfelt narrative.

     Amanda Dobbins [83:02]: "An amazing film about confidence and anxiety."

2. Oscar Nominee

   • Sean Fennessy: Selects The Fugitive, praising its action and storytelling.

     Sean Fennessy [36:41]: "The Fugitive is my pick for Oscar nominee."

   • Tracy Letts: Chooses Hoop Dreams, a highly acclaimed documentary.

     Tracy Letts [41:19]: "The best sports movie ever made, a real Chicago story."

3. Blockbuster

   • Sean Fennessy: Picks The Color of Money.

     Sean Fennessy [37:16]: "A quintessential Chicago movie with Paul Newman."

   • Amanda Dobbins: Chooses My Best Friend's Wedding, a beloved rom-com.

     Amanda Dobbins [73:08]: "A top five romantic comedy for me."

   • Tracy Letts: Selects The Untouchables.

     Tracy Letts [70:31]: "A delightful representation of Chicago."

4. Action/Horror/Thriller

   • Sean Fennessy: Drafts House of Games, lauding its intricate plot.

     Sean Fennessy [80:00]: "An extraordinary con man movie."

   • Amanda Dobbins: Picks Widows, commending its strong performances.

     Amanda Dobbins [65:50]: "A very Chicago movie with incredible cast."

   • Tracy Letts: Chooses Henry: Portrait of a Serial Killer, highlighting its chilling narrative.

     Tracy Letts [67:46]: "A terrifying depiction of Chicago's darker side."

5. Comedy

   • Sean Fennessy: Selects Wayne's World, embracing its cult status.

     Sean Fennessy [62:16]: "A classic Chicago movie beloved by many."

   • Amanda Dobbins: Chooses Ferris Bueller's Day Off, a personal favorite.

     Amanda Dobbins [38:57]: "A great teen movie about confidence and dancing in the streets."

   • Tracy Letts: Picks The Blues Brothers, celebrating its timeless humor.

     Tracy Letts [43:22]: "A rocking good time and a great comedy."

6. Wild Card

   • Sean Fennessy: Chooses Dark of the Moon, praising its thought-provoking narrative.

     Sean Fennessy [86:03]: "A film that changed the way I think about the world."

   • Amanda Dobbins: Selects While You Were Sleeping, a unique romantic comedy.

     Amanda Dobbins [93:35]: "A messed-up yet charming romantic comedy."

   • Tracy Letts: Picks Love Jones, admiring its emotional honesty.

     Tracy Letts [89:29]: "A beautiful, underseen story about young love in Chicago."

Discussions and Insights Throughout the drafting process, participants engage in spirited discussions about the eligibility of certain films, the portrayal of Chicago in cinema, and personal connections to the selected movies. Tracy Letts shares anecdotes from his theater background, emphasizing the cultural richness of Chicago's artistic scene.

A memorable exchange occurs when Sean connects his personal experiences with Chicago cinema:

Sean Fennessy [04:09]: "I haven't seen Neizia."

Amanda humorously contemplates the challenges of correctly placing movies within categories:

Amanda Dobbins [08:32]: "I'll take four out of five. Can anybody do four out of five?"

Tracy reflects on the significance of the Steppenwolf Theater in Chicago's theater landscape, offering deep insights into the city's theatrical prowess.

Conclusion As the draft concludes, the results reveal Amanda Dobbins as the winner of the trivia challenge with her picks for three out of five correct answers. The episode wraps up with heartfelt thanks to all participants, including Tracy Letts and Chris Ryan, and acknowledgments to the Steppenwolf Theater and the event team.

Amanda Dobbins [117:29]: "This was amazing. Thank you for voting for me."

Sean summarizes the evening's achievements and hints at future episodes, promising more engaging content and discussions about iconic films.

Sean Fennessy [119:00]: "Later this week we will be back with an episode about Fantastic Four's first steps. So this is going to be a cool week on the podcast."

The live episode successfully blends humor, competition, and in-depth discussions, celebrating Chicago's rich cinematic heritage and fostering a sense of community among movie enthusiasts.