The Rewatchables ‘Two for the Money’ With Bill Simmons, Chris Ryan, and Cousin Sal
11 snips
Nov 25, 2025 
Join Bill Simmons and Chris Ryan as they chat with Cousin Sal, a comedic force and gambling aficionado. They dive into the chaotic world of the 2005 film 'Two for the Money,' discussing its ties to early 2000s sports-advisor culture. Cousin Sal shares wild gambling stories while the trio hilariously critiques Pacino's commanding performance and McConaughey's charming persona. They also paint a vivid picture of outdated elements like fax machines and 900-numbers, while debating which film moments truly stand the test of time.
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The 900-Number Hustle
- Cousin Sal and Bill recall calling 900-number sports advisors in the 90s and being fooled by weighted “sucker lists.”
- Sal tells a story where his friend paid $400 for a tip that turned out to be Duke +17 and lost big.
Sports Advisors Were Proto-Substacks
- The sports-advisor era felt like the original Substack: paid picks, personality-driven, and high spectacle.
- Bill and Craig note modern paid-pick sites are the same product evolved with tech.
Gut Versus Analytics Theme
- The film intentionally pits gut-driven touting against analytics to capture a culture clash in sports betting.
- Chris Ryan highlights the movie’s antagonism toward analytics as a key theme.
