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401 – Playing By Heart

August 17, 2026 · 2 h 34 min

Show notes

Playing by Heart (1998) Directed by Willard Carroll Shown: Angelina Jolie, Ryan Phillippe

In the bygone moviegoing trend of “interconnected stories of Angelenos,” this week’s episode is a forgotten entry with a loaded cast. Playing By Heart from writer/director Willard Carroll follows multiple stories of romantic struggles, with Gena Rowlands and Sean Connery as a TV chef and her producer husband as the film’s epicenter. With themes of infidelity and HIV/AIDS throughout, the ensemble’s standout was a pre-Oscar Angelina Jolie as a manic actress chasing after a blue-haired Ryan Phillippe. While Miramax put its full weight into Shakespeare in Love, this film fell by the wayside in their awards lineup after mixed reviews.

This week, we talk about Jolie’s breakthrough years with Gia and her NBR prize for this film. We also discuss Gillian Anderson’s rare film performances, Ellen Burstyn serving Hannah Pitt, and Dennis Quaid’s deranged plot line of hoaxing strangers with sob stories at various L.A. bars.

Topics also include the original title “Dancing About Architecture,” AIDS onscreen post-Rent, and being haunted by April Grace.

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