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Sean Penn Had An Unlikely Pen Pal: The ‘Night Stalker’ Richard Ramirez

Photo Credit: Marc Piasecki / FilmMagic/ Getty Images
Photo Credit: Marc Piasecki / FilmMagic/ Getty Images

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).

Sean Penn and Madonna pose in black clothing in front of a blue backdrop on the red carpet.
Sean Penn and Madonna attend the 5th Annual Sean Penn & Friends HELP HAITI HOME Gala, January 9, 2016. (Photo Credit: Angela Weiss / Getty Images)

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.

Sean Penn in a leather jacket, light shirt, and jeans, walks behind a friend out of a building.
Sean Penn (left) leaves Los Angeles County jail after serving about half of his 60-day sentence for assaulting a movie extra and reckless driving, September 17, 1987. (Photo Credit: Bettmann / Getty Images)

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.

Richard Ramirez in a prison jumpsuit standing beside men in suits.
Richard Ramirez, better known as the Night Stalker, appears in court to fire his public defenders and hire a private attorney, October 9, 1985. (Photo Credit: Bettmann/ Getty Images)

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.”

More from us: These Brat Pack Film Facts Have Us Feeling Major ’80s Nostalgia

Despite his response, he still kept the original message from Ramirez until it burned inside Penn’s Malibu Hill house in a 1993 inferno.

Rosemary Giles

Rosemary Giles is a history content writer with Hive Media. She received both her bachelor of arts degree in history, and her master of arts degree in history from Western University. Her research focused on military, environmental, and Canadian history with a specific focus on the Second World War. As a student, she worked in a variety of research positions, including as an archivist. She also worked as a teaching assistant in the History Department.

Since completing her degrees, she has decided to take a step back from academia to focus her career on writing and sharing history in a more accessible way. With a passion for historical learning and historical education, her writing interests include social history, and war history, especially researching obscure facts about the Second World War. In her spare time, Rosemary enjoys spending time with her partner, her cats, and her horse, or sitting down to read a good book.