He has jumped into riots, protested against wars, drunk with dictators and aided natural disaster relief.
Now, Sean Penn has taken his boldest step yet in what appears to be a never-ending quest to ensure he is remembered as more than an actor. He found the world's most hunted criminal and asked him some questions for Rolling Stone magazine.
Why, you might have asked, would Joaquín "El Chapo" Guzmán sit down with the guy from Fast Times at Ridgemont High?
Because while you know Penn as a box office regular, the cartel kingpin knows him as a rebellious activist. Penn has been using his Hollywood power to jump into high-profile conversations for nearly the entirely of his career, from humanitarian moments in New Orleans and Haiti to political kerfuffles as controversial as this encounter with Guzmán.
"I take no pride in keeping secrets that may be perceived as protecting criminals," Penn wrote in his Rolling Stone piece, published on Sunday.
But as he was gearing up to meet the people who would eventually lead him to Guzmán, Penn said, he was in his "rhythm" - this was the kind of story he has been working towards for years, and not just because it might lead to a movie eventually. The escaped fugitive was "interested in seeing the story of his life told on film," if the project involved Mexican actress Kate del Castillo.
Presumably, he did not foresee that contacting two extremely famous actors would lead authorities to his capture last week.
A Mexican law enforcement official denied media reports that the Mexican government has requested to interrogate Penn. But the official added that "lines of investigation" could include Penn, without specifying how.
The actor's drive to be at the heart of the action seems to come from basic curiosity. A 2006 profile in the New Yorker describes how Penn drove into the thick of the Rodney King riots in Los Angeles in 1992 because he wanted to see it for himself. The adventure ended with a shopping cart crashing into his windshield.
"He's not taking a secondhand opinion. He really wants to know what's going down," actor-director Dennis Hopper told the magazine.
As his success continued on screen, Penn's growing reputation allowed for his curiosity to take him to more dangerous and exclusive places. In 2002, he travelled to Iraq. In 2003, after the invasion of US troops, he went back, this time to write about the experience for the San Francisco Chronicle. Penn enjoyed the experience of playing reporter enough to try it again in 2005, this time in Iran. Reporting, he told the New Yorker, was just like acting.
"You wake up in the morning with an interest in listening and expressing," he said. "It all feels the same to me. Acting is Everyman-ness, and loving Everyman. Finally, you're reaching out to people's pain."
Penn wasn't approaching turmoil in the Middle East as an unbiased journalistic observer. He had previously taken out an advertisement in the Washington Post condemning President George W. Bush on Iraq, and later called for his impeachment.
"The needless blood on your hands, and therefore, on our own, is drowning the freedom, the security, and the dream that America might have been, once healed of and awakened by, the tragedy of September 11, 2001," Penn wrote to Bush in 2010.
Though he allegedly tried to interview Bush, Penn never made it to the White House. Instead he veered towards a different brand of world leader, developing relationships with Cuban President Raúl Castro and Venezuela's late Hugo Chávez.
Penn visited Cuba for Christmas in 2005, "under the auspices of religious tourism," with his then-wife Robin Wright and their two children. The family was introduced to Castro in a private midnight meeting, where they discussed the actor's trips to the Middle East, Latin American history and gay rights.
Penn wrote about the encounter in a 17,000-word story for The Nation, in which he also describes meeting and befriending Chávez. When Chávez died in 2013, Penn called him one of the "most important forces we've had on this planet".
This is apparently what piqued Guzmán's interest in Penn.
"He asks about my relationship with the late Venezuelan President Hugo Chavez with what seems to be a probing of my willingness to be vilified through associations," Penn wrote in Rolling Stone.
"I speak to our friendship in a way that seems to pass an intuitive litmus test measuring the independence of my perspective."
When he flew to the post-disaster scenes of Hurricane Katrina and the Haiti earthquake, Penn was accused of showboating. He responded by saying he hoped those critics would "die screaming of rectal cancer," then founded "J/P Haitian Relief Organisation."
The non-profit held a benefit gathering the same evening as the Rolling Stone interview Guzmán with was released.
"I'm just another a-- trying to feel good about himself," he told Esquire last year. And why shouldn't I? That's what everybody should try to do."
"I'd seen plenty of video and graphic photography of those beheaded, exploded, dismembered or bullet-riddled innocents, activists, courageous journalists and cartel enemies alike," he wrote.
"I was highly aware of committed DEA and other law-enforcement officers and soldiers, both Mexican and American, who had lost their lives executing the policies of the War on Drugs. The families decimated, and institutions corrupted."
It's just the kind of thing that would make a captivating movie, perhaps one day, starring Sean Penn.