
The Rewatchables “The Re-Departed” With Bill Simmons, Chris Ryan, and Sean Fennessey
10 snips
Oct 5, 2021 Bill Simmons, Chris Ryan, and Sean Fennessey rewatch "The Departed" and discuss its unique storytelling style, top-notch performances, and themes of identity and fathers and sons. They delve into Al Pacino's acting approach, Leonardo DiCaprio's Oscar controversy, and the shocking death of a character. They also explore the inaccurate portrayal of Whitey Bulger in movies and TV series, compare scenes from "Infernal Affairs" and "The Departed," and analyze the absurdity and maximalism of the film. The hosts debate the opening montage, discuss what has aged poorly, and examine Boston's misrepresentation in films. They consider alternate casting choices, recognize memorable supporting performances, and explore the impact of the song "Shipping Up to Boston." Lastly, they speculate about a future episode with Michael Mann.
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Episode notes
X Motif As Death Foreshadowing
- The film uses recurring visual motifs (X marks) to signal doomed characters and build thematic cohesion.
- These layered images quietly foreshadow mortality across the movie's chaotic editing.
Oscar Win In Context
- The Departed's Academy success reflected a weak Oscar year, not unanimous consensus on its superiority.
- The win gave Scorsese the overdue trophy but sits amid debate about that year's strongest films.
Baldwin And Wahlberg's Rewatchable Beats
- The Baldwin driving-range scene and Wahlberg's opening with DiCaprio are repeatedly called rewatchable for their comic and character-rich beats.
- Hosts say those scenes deliver prime Boston flavor and memorable dialogue.



