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For hitting a photographer, actor Sean Penn was sentenced to thirty-two days in the Los Angeles County Jail. Due to his celebrity status, he had to be kept in protective custody, and was placed in the cell next to Richard Ramirez. Sean Penn’s then-wife Madonna caught sight of Ramirez when she came to visit Sean. In the visiting booth, she demanded to know who the “good-looking” guy was, and was informed that he was the infamous Night-Stalker.

During the course of Sean Penn’s stint in jail, he met Ramirez because they had to take showers at the same time because we were both high-priority inmates, each had high profiles. There were threats on then both. During their time together, Richard Ramirez asked him for his autograph. Sean Penn agreed saying,“I’ll give you mine if you’ll give me yours.“

Paper passing was contraband, so Penn asked a guard if he could give them a free pass and, playing cupid in the situation, he agreed. He brought over Ramirez’ autograph. It read, “Dear Sean: Stay tough and hit ‘em again. Richard Ramirez, 666.” It included a pentagram and a very good illustration of his view of the Devil.”

So Penn then wrote Ramirez back something to the effect of, “Dear 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. He got a kick out of it. He had a sense of humor.”  

When asked if he felt sorry about those incarcerated, Penn later said about Richard.”Ramirez was odd. He was like a textbook psycho. He was funny. What he did was obviously horrible, but in jail, he was like the typical bad actor. He was like the psychos on The Mod Squad. He’d jerk off a lot when nurses were around. He’d start jerking off and laugh this manic laugh. Yeah, he was a big star there. “