Madonna’s ex-husband, Sean Penn, has revisited one of the darkest encounters from his time behind bars. The actor was married to Madonna when his 1987 jail sentence placed him near notorious killer Richard Ramirez.
The Oscar winner’s time in Los Angeles County Jail led to an autograph request he never expected.
Sean Penn opened up about the unsettling jail encounter with the infamous killer
In a recent VICE News interview, Penn recalled spending more than 30 days in Los Angeles County Jail while Richard Ramirez was housed nearby. Ramirez, later convicted as the serial killer known as the Night Stalker, was awaiting trial.
Penn received a 60-day sentence for reckless driving and punching an extra on the set of Colors. He served 33 days in 1987 and said Ramirez was positioned across from him in a high-security area.
After about a month, a deputy approached Penn and said Ramirez wanted his autograph. Penn did not immediately agree. He asked for a sergeant to approve the exchange and insisted that Ramirez send him a note first.
According to Penn’s earlier account, Ramirez wrote, “Hey Penn, stay tough and hit them again,” before signing his name alongside “666,” a pentagram and a drawing of the devil.
Penn’s reply made his feelings unmistakable. He wrote that incarceration usually created some connection among inmates, but told Ramirez, “I feel absolutely no kinship with you.” He also said he hoped the gas chamber reached Ramirez before sanity did.
The Sean Penn-Night Stalker encounter ended with that brief exchange. Penn kept Ramirez’s note for years, but said it was later destroyed when his Malibu home burned.
Ramirez was convicted in 1989 of 13 murders and numerous other crimes. He received a death sentence and remained on death row until his death from cancer-related complications in 2013.
The unsettling Sean Penn jail story unfolded during his marriage to Madonna, which lasted from 1985 to 1989. Their relationship has continued to generate attention, including speculation that Madonna’s new music referenced Penn.
Penn has also faced backlash over comments about selfies and drew attention when he reportedly skipped the 2026 Oscars despite winning another Academy Award. Neither headline compares with being housed near one of California’s most infamous killers.
Penn’s response showed that even behind bars, he wanted Ramirez to know there would be no celebrity endorsement or friendly connection.
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