He shot at helicopters on the day he married Madonna, was arrested for dangling a photographer from a hotel balcony and has socialised with dictators and drug lords.
Sean Penn seemed to be rewriting the Hollywood hellraiser’s training manual.
But that was then – and today the star is intent only on good works.
Penn’s bad boy behaviour was seemingly atoned for when he rescued survivors of Hurricane Katrina in New Orleans in 2005.
But whatever his reputation, Penn has no desire to follow his acting peers into middle-aged sobriety and suburbia.
And on the eve of his 60th birthday, the actor claims he is not interested in holding on to his youth.
He said: “I’ve always thought of myself as a natural-born 77-year-old, so I’ve got 17 years before I’m going to feel like me.
“I’ll finally get 60 done so I can get on to 61, 62, and onwards to 77.
“When people ask that question on psychological profiles – ‘What age do you see yourself most comfortably?’ – for me, I don’t know why, but it’s always 77.”
This summer, the volatile star walked down the aisle for a third time to marry 28-year-old Leila George.
The Australian-born actress-turned-charity worker just happens to be the daughter of screen stars Greta Scacchi and Vincent D’Onofrio and is chief of staff for Community Organised Relief Effort – CORE – the non-profit group that Penn founded.
He insists that any potential birthday party will be low key and up to his new wife to organise.
Penn said: “For anyone who knows wonderful Australian women, they know that they are in command of any celebrations that happen.
"So that’s lying in wait for me… or it’s not. But in any case, because she is a diligent worker in Covid-19 response, any celebration that might happen will be under very rigid policy with very few people.”
Penn has a catalogue of beautiful ex-lovers, having enjoyed flings with scores of screen beauties including Elizabeth McGovern, Susan Sarandon and Charlize Theron.
His first bride was Madonna. The pair tied the knot in 1985 but their four-year marriage was fiery from the outset.
Tennis ace John McEnroe, who witnessed the couple together, said he was amazed the relationship lasted for as long as it did.
He said: “They didn’t throw punches in front of me but you could see that Sean is a very intense person. It seemed a normal thing 30 years ago.”
Since their split in 1989, Penn and Madonna have remained on good terms, with the actor publicly admitting that he still loves his first wife “very much”.
And at a 2016 fundraiser in Malawi, Madonna told her ex: “I’m still in love with you, yes. In fact, I think I love you more now that we’re divorced.”
Penn, who was also married to actress Robin Wright from 1996 to 2010, was born into showbusiness as the son of director Leo Penn and actress Eileen Ryan
By the age of 22, he was hailed as the finest actor of his generation after a tour de force performance in 1983 film, Bad Boys.
But Penn chose to avoid the Hollywood blockbusters favoured by the likes of Harrison Ford and Tom Cruise.
He once said: “I think a movie like Raiders of the Lost Ark is just like taking drugs. I’m against the whole idea of, ‘Oh, it’s good entertainment.’”
Despite being worth an estimated £115million, dad-of-two Penn is not a big spender. He said: “I’m not big on fancy houses, I’m not big on fancy cars, but I do like to get up and go and do the things I want to do.
“I’m not thinking so much about spending money right now. I’m thinking about how I’m going to make some.” Penn’s performances in Mystic River and Milk earned him Best Actor Oscars in 2004 and 2009, respectively.
But after starring in more than 50 films, it seemed natural for Penn to move from acting to directing.
In 2007 he received a Directors Guild of America nomination for Into the Wild and has just directed his two children – Dylan, 29, and Hopper, 27 – in Flag Day, which is about the daughter of a con artist who struggles to come to terms with her father’s past.
Penn said: “Directing Dylan was exhilarating and terrifying. When I said ‘Action’ the first time, I watched and felt every jaw on the crew drop.
“She turned out to be a miraculous truth machine and it was thrilling, really thrilling. She didn’t make it easy – no Aries woman would – but she made it possible. It’s pretty exciting for your favourite actress in the world to be your daughter, and to watch her work.”
In the last ten years, Penn – whose friendship with the late Venezuelan dictator Hugo Chávez sparked outrage – has been on a mission to rebuild Haiti after a devastating earthquake in January 2010 killed more than 300,000 people.
He has also published a host of opinion pieces, interviewed drug kingpin Joaquin “El Chapo” Guzman for Rolling Stone magazine and written two books about Bob Honey – a fictional septic tank entrepreneur turned mallet-wielding assassin.
Penn certainly isn’t afraid to say what he thinks. And when it comes to how the coronavirus pandemic has been handled, he is particularly vocal.
“When I see people who self-righteously say that this thing doesn’t exist or, ‘I am not going to wear a mask and you can’t contact trace me,’ well, you people are violating my civil liberties,” he said. “We all have to stand together.
“I’ve had friends who have suffered tremendously and I’ve had friends who tested positive but for the most part were asymptomatic. This is dangerous in ways that we don’t know yet.
“I’m torn between pragmatism and optimism. But we will survive this.”