Sean Penn is a well-known name in Hollywood. His marriage to Madonna only increased his popularity, but his time as an actor and director is what he is truly famous for. Yet there are a few shocking elements of his life that are often forgotten. Not only has he been to jail on more than one occasion and conducted a slightly underwhelming prison break, but he ended up briefly becoming pen pals with none other than the notorious serial killer, the Night Stalker.
Actor and director
Over the years, Penn has created an impressive résumé. His first foray into Hollywood was as an extra in Little House on the Prairie in 1974. In 1981 he played a minor character in the film Taps. It wasn’t until the following year that he took on the role of Jeff Spicoli in Fast Times at Ridgemont High. This helped catapult his career. From there, he continued to impress audiences with a string of powerful performances in films like Dead Man Walking (1995) and Mystic River (2003).
He received Academy Award nominations for both, winning Best Actor for the latter. His second Oscars win came for his role as Harvey Milk in the 2008 film Milk. Despite achieving fame as an actor, Penn has never shied away from exploring new territories in the film industry, and he demonstrated his directorial talents with the critically acclaimed dramas The Indian Runner (1991), The Crossing Guard (1995), The Pledge (2001), and Into the Wild (2007).
Jail time
Despite his rising career, Penn was also jailed more than once in the 1980s. The first instance was when he and then wife, Madonna, were staying in a Macau hotel when a man accosted the actor. He and his personal assistant “grabbed the guy, ran him through the room to the balcony and hung him over — on the ninth floor.” Soon enough, they were both taken to jail, except they weren’t shut in properly. Instead of staying put, they both walked out and flew to Hong Kong.
The second incident occurred in 1987 after Penn punched an extra on the set of Colors. This, combined with a reckless driving charge, earned him 60 days in the Los Angeles County jail. It was while there that he had a strange encounter with Richard Ramirez. Penn recounted his strange experience with the Night Stalker while he was incarcerated in a nearby cell. After a while, Ramirez had clearly noticed the actor and decided he wanted an autograph
An unlikely pen pal
Penn explained, “he sent one of the deputies over, deputy came to my cell and told me, ‘Hey, you know, Richard Ramirez wants your autograph.'” He only agreed to do it if the sergeant approved it, which he did: “So they went over to Ramirez and, you know, this guard basically wanted to play Cupid in some way. We were both on 24 lockdown…but so I get this thing from him and it says, ‘Hey Sean, stay tough and hit them again. Richard Ramirez, 666,'” including a petagram and devil.
Before you worry that Penn started a lengthy correspondence with a serial killer, he didn’t. Instead, he responded, “Richard, it’s impossible to be incarcerated and not feel a certain kinship with your fellow inmates. Well Richard, I’ve done the impossible, I feel absolutely no kinship with you. And I hope gas descends upon you before sanity does…it would be a kinder way out.”
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Despite his response, he still kept the original message from Ramirez until it burned inside Penn’s Malibu Hill house in a 1993 inferno.