The Rewatchables

‘The Legend of Billie Jean’ With Bill Simmons and Chris Ryan

Sep 9, 2025
Dive into 1980s nostalgia as the hosts reminisce about 'The Legend of Billie Jean,' exploring its themes of female empowerment and iconic moments. They humorously compare the fast-paced movie industry to a football game, reflecting on memorable character dynamics and absurd portrayals. The duo critiques the film's box office performance while sharing laughs about hairstyles and celebrity culture. Join them for a whimsical journey through iconic fashion, unforgettable cars, and your favorite nostalgic flicks that shaped an era.
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INSIGHT

Early Viral Fame And Empowerment

  • The film prefigures modern viral fame and female empowerment tropes long before the internet era.
  • Billie Jean's rise shows how notoriety and fame blur, foreshadowing later media phenomena.
INSIGHT

Movie As A Precursor To Media Culture

  • The hosts connect the movie's media themes to later celebrity scandals and instant notoriety.
  • They argue the film captures a turning point where cable and video began manufacturing fame.
ANECDOTE

’80s VHS Camera Memories

  • Bill Simmons recounts owning a heavy VHS camcorder and making student films in high school.
  • He describes editing on two VCRs and the frantic rush to capture shots before batteries died.
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