Never one given to convention, two-time Oscar winner Sean Penn is candid about his disappointment with the general state of movie-making in Hollywood and how he at one point even considered retiring from acting. “I’m 54 years old, I’ve smoked a lot,” said the star of upcoming drama The Gunman, which is scheduled for a 20 March opening, “so I don’t know how much time I’ll (have), you know? We’ll see. I will probably act many more times, but I won’t be disappointed if I don’t. If I don’t make a few of the films I want to make as a director, I’ll be disappointed.” He was addressing students at the Loyola Marymount University&’s School of Film and Television on 4 March.

In a wide-ranging conversation that encompassed the 1950s Hollywood blacklist, attempts to improve conditions in Haiti (where Penn has been running a refugee camp) and the state of American film, Penn — who was taking part in the ongoing Hollywood Masters interview series moderated by The Hollywood Reporter&’s Stephen Galloway — also recalled one especially unusual encounter — with serial killer Richard Ramirez. (Penn likely crossed paths with Ramirez when he was serving a brief jail term in 1987 for probation violations)

“He wrote me (a letter,” he said. “I was down here on Bauchet Street, in LA County Jail, in the cell kind of across from him. And after about a month of seeing each other around, he wanted my autograph. So he sent one of the deputies over, (and the) deputy came to my cell and told me, ‘Hey, Richard Ramirez wants your autograph.’ And I didn’t trust the deputy, because I’d gotten in some trouble inside there, and just passing a piece of paper is contraband, so you can get extra days for that and I already had extra days and I didn’t want more. “So I said, ‘Bring the sergeant down here, and I’ll talk to him, and if he approves it. Then I want him to write something first and I’ll write him something back.’ So the sergeant came down and approved it and they went over to Ramirez — this guard basically wanted to play Cupid in some way. So I get this thing from him and it says, ‘Hey, Sean, stay tough and hit them again — Richard Ramirez, 666,’ with a pentagram and a rendition of the devil.” Penn wrote back, “I said, ‘You know, 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, you know? It would be a kinder way out.’ And they gave it to him. And then my house burned down years later and that damn thing of his burned with it.”

The filmmaker, whose pictures include Mystic River, Fast Times at Ridgemont High and Dead Man Walking, also spoke of his disappointment with the current state of motion pictures, which led him to think of retiring as an actor at one point. “I really got disenchanted,” he said, “and I thought I was done. I’m born in 1960, so that puts me in what for anybody who&’s studying film should know is an extraordinary age of eating cinema. You know, if you’re going to the restaurant of cinema, in the 1970s in this country, every weekend is an event that has lasted to this day. I mean, such extraordinary American films. That was what I was entering, that&’s the business that I’m going into. (But) it died with another cinema&’s (birth). “At that time, the very best art films were the biggest movies of the year. And people in Hollywood dined out on, ‘Oh, you know, we made $60 million.’ And then I came out, and $60 million was like Dr Evil saying ‘$1 million!’ It started to move towards where it is today. Rather than building a career as an actor you’re looking to win a contest to be in a movie. It&’s different. You know, Dustin Hoffman said — I had dinner with him one night, and he said, ‘You’re not retired, you’re disappointed.’”

Penn addressed his ongoing issues with the invasion of privacy, to which public figures are subject. “I hear people talk about privacy and the importance of privacy, and now that Pandora’ Box has opened with social media, the Internet and so on,” he said, “and virtually anybody can be hacked and will be. And I believe that within a year from now, any wife or husband, any parent, is going to be able to access everybody&’s entire email history and text history and photography history, no matter how many times you’ve deleted it.

Everybody&’s going to have access to everyone&’s history and all of it&’s going to come out. Do I care a lot about people&’s privacy and how that&’s going to affect them? Not if they ever bought a People magazine, because they’ve been doing it to me for 30 f…ing years. Guess what, you know, the only way you deserve privacy is if you promote privacy. And the culture has not. It&’s run around, pulling people&’s pants down, like a bunch of silly children. And I just think it&’s taken us down a notch in everything that we aspire to.” Asked about the status of the refugee camp he has operated since the devastating 2010 earthquake in Haiti, he replied, “We’ve relocated all 60,000 (refugees in the camp),” while acknowledging that at one point the sheer scale of the disaster proved almost too much. “The only time that I was really overwhelmed was a month after we arrived,” he said. “I had gotten to know Port-au-Prince (well). And all of those references had disappeared.

It all felt fixable until I went up in a helicopter the first time and we were delivering some supplies across the country. (There was) an incredible amount of pain, and just for a moment I felt that it could never be fixed.”