What Sean Penn's Life In Jail Was Really Like

Sean Penn has lived many lives, and one of them included a short stint in jail because of his actions on a 1987 movie set. According to the Los Angeles Times, Penn, who was already on parole because of a serious incident involving assault, got physical with an extra, who decided to make their time on the "Colors" set together last longer — i.e. he took his photo. In response, Penn reportedly punched the man, whom the publication identified as Jeffrey Klein. The star was unable to avoid jail time on the back of his celebrity. By June, a judge had handed Penn a 60-day jail stint, due to start in July of that year.

At the time, Howard L. Weitzman, who represented him through his legal trouble, spoke on Penn's behalf, conveying his apparent remorse over the incident. "He feels this is an unfortunate experience," said the attorney (via the Los Angeles Times). "He has to learn that people are going to attempt to goad him into situations where he may react inappropriately." He continued, "He needs to and does understand that incidents like this are inescapable and he can control and will control them." Whether or not Penn actually walked away from the incident with a newfound perspective, well, we'll get to that later. 

What's certain, however, is that Penn crossed paths with a terrifying figure ... and he lived to tell the tale.

According to the Los Angeles Times, Sean Penn was supposed to start his jail sentence in July 1987. However, he didn't actually check into the jail until August 3, 1987, because the judge over his case honored the scheduling conflicts with his filming schedule, according to UPI. While Sergeant Terry Padilla assured the publication that Penn wore the "same jail clothing, eats the same food and has the same privileges as our other prisoners," at the Mono County Jail, he was able to spend his time in lockup at the smaller, less dangerous facility — to the tune of $75 a day (which amounted to $4,500 for 60 days).

Interestingly, he still crossed paths with dangerous serial killer, Richard Ramirez, also known as The Night Stalker. During a panel at Loyola Marymount University, Penn revealed that he sent Ramirez a note after a deputy revealed that the murderer had requested an autograph. "But so I get this thing from him and it says, 'Hey Penn, stay tough and hit them again. Richard Ramirez, 666' with a pentagram and a rendition of the devil," he said (via The Hollywood Reporter). "I said, you know, Richard it's impossible to be incarcerated and not feel a certain kinship with your fellow inmates. Well Richard ... I feel absolutely no kinship with you. And I hope gas descends upon you before sanity does ..."

Well, we did say he's lived several lives. 

By 2023, Sean Penn's brief stay in jail was about 36 years in his past, but he reminded everyone about his trip behind bars after Will Smith waltzed onstage and slapped Oscars presenter Chris Rock during the 2022 Academy Awards. As the world reacted to Smith's out-of-character behavior, Penn joined the ranks of his many, many detractors. "I don't know Will Smith. I met him once. He seemed very nice when I met him. He was so f***ing good in 'King Richard,'" he prefaced his comments to Variety in 2023. "So why the f*** did you just spit on yourself and everybody else with this stupid f***ing thing? Why did I go to f***ing jail for what you just did? And you're still sitting there?" he added.

Given Penn's own history with violence, some questioned his right to take this stance. "Kind of ironic that this guy of all people is gonna act outraged by violence with his history," commented one fan on Reddit. "Sean Penn had been and has always been an enormous prick all of his life," argued another fan. "He was so quick to jump all over Chris Rock at an awards show for making a joke. So quick to defend him after the Smith assault despite all of Penn's violent and covered-up antics." Some fans also questioned the timing of Penn's commentary about the viral moment, which took place over a year earlier. "Wow Sean thank you for finally speaking on this...over a year later," wrote one fan.