Sean Penn: Hollywood hellraiser turned activist

Madonna and Sean Penn had a tempestuous 1985-1989 marriage but are said to remain close

Sean Penn is one of the more colourful Hollywood stars of recent decades, emerging from his early incarnation as a hard-drinking young Hollywood actor to become a double Oscar winner and high-profile campaigner on social and political issues.

The 55-year-old's secret interview in the Mexican jungle with fugitive Joaquin "El Chapo" Guzman, published in Rolling Stone shortly after the notorious drug lord was recaptured, is just his latest brush with controversy.

Penn was a noted critic of the administration of President George W Bush, visiting Baghdad ahead of the 2003 US-led invasion of Iraq which he firmly opposed. He also met Washington betes noires like Venezuelan President Hugo Chavez and Cuban leader Raul Castro.

Meanwhile, his personal life - involving marriages and relationships with high-profile women including Madonna, Scarlett Johansson and Charlize Theron - has become the stuff of tabloid legend.

Born in 1960 in Los Angeles, the son of actor and director Leo Penn and actress Eileen Ryan, Sean was one of three brothers. Childhood friends included Emilio Estevez and Charlie Sheen, both of whom would also go on to become successful actors.

Appearances on US TV in his early teenage years - the first a cameo in the popular western series Little House on the Prairie - started his acting career, which took off after his central role in the 1983 film Bad Boys, a crime drama mostly set in a juvenile detention centre.

The 1980s also saw him marry Madonna, then as now one of the best-known pop singers on the planet. Their supposedly private wedding on a Malibu clifftop was an occasion that saw several media organisations deploy helicopters that buzzed the ceremony in an attempt to film and photograph the happy couple.

Back in the day: Sean Penn and Madonna, seen here in 1986, have not faded from public view

The often tempestuous marriage, characterised by frequent rows and Penn's fraught relationship with press photographers and cameramen, lasted four years and saw the couple star together in the 1986 film Shanghai Surprise - a widely derided box office flop.

Penn's next serious relationship was with actress Robin Wright, with whom he went on to have two children and a 14-year marriage. It was eventually dissolved after several withdrawn divorce petitions by both parties.

Despite once being quoted as describing awards seasons as times "where manipulation and very good marketing are rewarded", Penn has been nominated five times as best actor in the Academy Awards, initially in 1996 for his role as a racist murderer on death row in Dead Man Walking.

He has won the Oscar twice, in 2003 for his role as an ex-convict Boston shopkeeper in Mystic River and in 2008 for his portrayal of a gay rights activist and politician in Milk, a performance that led director Gus Van Sant to describe him as "the Brando of our generation".

He has also worked extensively behind the camera, directing both films and music videos for singers including Shania Twain.

Penn on meeting Guzman:

"I search the skies for helicopters. There is no question in my mind but that the DEA [US Drug Enforcement Agency] and the Mexican government are tracking our movements."

"He is interested in the movie business and how it works. He's unimpressed with its financial yield... He suggests to us that we consider switching our career paths to the oil business."

"I will discover that his already accomplished engineers had been flown to Germany last year for three months of extensive additional training necessary to deal with the low-lying water table beneath the prison. A tunnel equipped with a pipe-track-guided motorcycle with an engine modified to function in the minimally oxygenised space, allowing El Chapo to drop through a hole in his cell's shower floor, into its saddle and ride to freedom."

Winning an Oscar for playing Harvey Milk - the first openly gay person to be elected to public office in California - gave Penn a platform to voice support for gay marriage, but he had already tied his colours to the liberal mast with his vocal opposition to the policies of the Bush administration, in particular the invasion of Iraq.

He visited Baghdad to express solidarity with the Iraqi people a few months ahead of the US-led invasion. "Sacrificing American soldiers or innocent civilians in an unprecedented pre-emptive attack on a separate sovereign nation may well prove itself a most temporary medicine," he said at the time.

He also developed a friendly relationship with Venezuela's socialist President Chavez, another staunch critic of President Bush, and - in a foretaste of his Guzman interview - was allowed to question Cuban leader Raul Castro in the run-up to the 2008 US presidential election that foreshadowed a softening of US policy towards the communist island.

But Penn has also become known for his humanitarian work, including during the chaotic aftermath of the hugely destructive earthquake that hit Haiti in January 2010.

The actor spent time in Haiti, helping to dispense food and medicine and even reportedly sweeping floors. He went on to found the J/P Haitian Relief Organization, which employs hundreds of people working on development projects in the poor Caribbean nation.

Broken engagement

Five years before and closer to home, Penn got involved in the rescue effort after Hurricane Katrina devastated parts of the US Gulf Coast.

"Displaying a mix of bravado, altruism and daredevil recklessness, he repeatedly swam over to trapped homeowners to take them to higher and drier ground," Vanity Fair reported.

More recently, Penn has enjoyed romantic relationships with actresses Scarlett Johansson and Charlize Theron, the latter ending abruptly last year when Theron reportedly broke off their engagement.

Despite having divorced more than a quarter of a century ago, Penn and his first wife remain close.

As news of his interview with Guzman broke, Madonna accompanied Penn to a benefit concert in Beverly Hills for his Haiti charity, where she was one of the acts performing.

At the event Penn spoke passionately about his charity's work in Haiti. "We can't depend on governments," he said. "We have to make it better now."

But Republican senator and presidential candidate Marco Rubio was more interested in Penn's interview with the Mexican drug lord.

"If one of these American actors who have benefited from the greatness of this country, who have made money from our free enterprise system, want to go fawn all over a criminal and a drug trafficker in their interviews, they have a constitutional right to do it," he told ABC News. "I find it grotesque."