39 minutes | May 25, 2022

Sean Penn: A Prison Escape, The Night Stalker, and Madonna’s True Blue Bad Boy

In the summer of 1985, Sean Penn’s marriage to preeminent material girl Madonna was an epochal moment for ‘80s-era Hollywood. The bad boy from Bad Boys and the boy-toy pop superstar blissfully brought together the worlds of movies and music on a Malibu bluff overlooking the Pacific. But their subsequent attempt to make a movie together was anything but blissful. A wild film shoot in China would lead to even wilder things, like the time Sean dangled a photographer upside-down from a ninth-story balcony. Or the time he escaped a prison in Macau and had to have a pardon from the government negotiated by a former member of the Beatles. Or the time he spent in an American prison, where he found himself passing notes with a fellow inmate down the hall…one who happened to be one of the most notorious serial killers in history.

This episode contains themes that may be disturbing to some listeners, including domestic violence and sexual assault.

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