‘Two for the Money’ Rewatchables Breakdown

Bill Simmons, Chris Ryan and Cousin Sal dive into the wild world of 2005’s sports-betting drama Two for the Money (starring Matthew McConaughey, Al Pacino and Rene Russo), all while placing their own imaginary Monday night parlays. They kick things off with a cold open before analyzing how the movie handles the highs and lows of wagering big, sharing plenty of behind-the-scenes trivia along the way.

What Makes It Rewatchable

After hashing out the film’s best betting scenes, the crew picks their single most rewatchable moment and then fires off a rapid-fire “Categories” round to rank everything from standout performances to jaw-dropping plot twists. It’s equal parts film deep-dive and friendly smack talk—perfect for sports-movie junkies.

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