Bill Simmons is joined by his buddy JackO who gives his thoughts on the Red Sox firing their GM, Dave Dombrowski, the surging Yankees, the Democratic presidential candidates, and more (4:10). Then Bill sits down with Academy Award–winning actor Sean Penn to discuss his long career, his new novel Bob Honey Sings Jimmy Crack Corn, what he’d learned from Clint Eastwood, Jack Nicholson, and David Fincher, and more (33:08).

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