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.

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The mysterious death of Brittany Murphy. David Lynch and the real-life brutal murder that inspired Twin Peaks. Steve McQueen’s brush with Charles Manson. The three conspiracies surrounding Marilyn Monroe’s death. The indecent arrest of John Waters. Dennis Hopper’s easy riding and excessive 70s Hollywood. Woody Harrelson’s Dad’s connection to the JFK assassination. The obsessive murder of Dorothy Stratten. Bill Murray’s bust. Chris Farley burning out too soon. Al Pacino’s armed robbery. The serial killer and Gianni Versace. Heath Ledger’s overdose. If it’s a story that meets up at the corner of Hollywood and True Crime, then it’s an episode of HOLLYWOODLAND, the show that explores the lives of our most celebrated actors and actresses through the true crimes that have most impacted them. Hosted and produced by award winning podcaster Jake Brennan, creator of DISGRACELAND, HOLLYWOODLAND is the first true spin-off of DISGRACELAND and is produced similarly with edge-of-your-seat storytelling and gripping, immersive sound design by the folks at Double Elvis. Episodes are roughly 30 minutes long and released every Monday.

• No. of episodes: 46
• Latest episode: 2025-04-28
• History True Crime

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