‘Two for the Money’ Rewatchable Breakdown

Bill Simmons, Chris Ryan and Cousin Sal dive back into the 2005 sports thriller Two for the Money, starring Matthew McConaughey, Al Pacino and Rene Russo. They kick things off with a cold open before digging into the film’s high-stakes betting scenes (1:53), debating the single most rewatchable moment (30:13) and rolling out their signature “Categories” segment at 48:33.

Along the way you get that classic Ringer camaraderie—sharp takes, playful jabs and a favorite Monday night parlay vibe—peppered with sponsor shout-outs from Subaru’s Share the Love event and a friendly State Farm reminder. It’s part sports analysis, part movie club, and all about the gamble.

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