San Francisco Frontiers - Sean Penn: Hollywood's rebel with a cause wins third Oscar

After previous lead actor Oscars for "Mystic River" and "Milk," the best supporting actor win makes Penn just the eighth performer in Academy Awards history to pick up a trio of golden statuettes.

Penn fended off his "One Battle" co-star Benicio Del Toro, as well as Delroy Lindo ("Sinners"), Australia's Jacob Elordi ("Frankenstein") and Sweden's Stellan Skarsgard ("Sentimental Value").

Famed for both his powerful, challenging performances and his disdain for Hollywood's awards circuit, Penn did not attend Sunday's Oscars gala.

In "One Battle After Another," he plays Colonel Steven Lockjaw, a ramrod military officer who briefly succumbs to his passion for revolutionary Perfidia Beverly Hills (Teyana Taylor).

Years later, he literally mobilized an army to prevent that brief indiscretion from destroying his political ambitions.

The character could hardly be further from the real Penn, whose liberal views and social activism have led him to adventures that seem straight out of a movie.

Most famously, in 2015 he secretly traveled to a clandestine location in Mexico to interview drug lord Joaquin "El Chapo" Guzman, not long before the notorious crime kingpin's arrest.

He befriended Hugo Chavez, the then-leader of Venezuela and fierce nemesis of Washington, and gave his "Mystic River" Oscar to Ukrainian President Volodymyr Zelensky, saying it could be melted "down to bullets they can shoot at the Russians."

- Married to Madonna -

Born in August 1960 in Los Angeles to director Leo Penn and actress Eileen Ryan, Penn grew up in the industry that he has so often infuriated by refusing to play its game, and abandoned his dream of being a lawyer to study acting.

In 1981, he made his Broadway debut in the play "Heartland" and his movie debut that same year as a military cadet in "Taps." He won some fame as a surfer dude in Amy Heckerling's 1982 hit teen flick "Fast Times at Ridgemont High."

It was arguably not his acting that first propelled him to global celebrity, but his 1985 marriage to pop star Madonna, with whom he co-starred in the universally-panned 1986 mega-flop "Shanghai Surprise."

After four years of turbulent marriage, during which he served 32 days in jail in 1987 for hitting a movie extra, the pair divorced.

But while Penn's romances have had their well-chronicled highs and lows, his acting career only followed one trajectory: up.

Penn took starring roles in films such as "Colors" (1988) opposite Robert Duvall, as a brutal sergeant in Brian de Palma's "Casualties of War" (1989) and in the 1989 comedy "We're No Angels" with Robert De Niro.

In 1991, he made his directorial debut with "The Indian Runner," an impressive Vietnam War-themed drama inspired by a Bruce Springsteen song.

Penn appeared as a reptilian lawyer in the 1993 thriller "Carlito's Way," before saying he was retiring from acting to direct, and making 1995's "The Crossing Guard" with Jack Nicholson and Anjelica Huston.

In 1995, Penn was lured back to the screen by friend Tim Robbins, earning his first Oscar nomination for the death row tale "Dead Man Walking."

As his bad boy image began to wear off, he garnered two more Academy Award nods for "Sweet and Lowdown" (1999) and for his role as a mentally disabled father in 2001's "I Am Sam."

- 'Milk' -

In 2004, Penn finally converted an Oscar nod into a win with Clint Eastwood's drama "Mystic River," in which he plays a grieving father who takes justice into his own hands.

He would triumph again five years later with "Milk," in which he portrayed Harvey Milk, the San Francisco activist who became one of the first openly gay men elected to US public office.

In the ensuing years, Penn took fewer major movie roles as he pursued his own activism.

In 2013, Penn organized a brilliant operation to smuggle Jacob Ostreicher, an American businessman under house arrest in Bolivia on suspicion of organized crime and money laundering, out of South America using false documents.

He has also spearheaded humanitarian campaigns, including the Hurricane Katrina response in New Orleans, and in Haiti after the impoverished Caribbean nation's 2010 earthquake.

But "One Battle" has put the 65-year-old firmly back at the heart of Hollywood.

He joins Daniel Day-Lewis, Jack Nicholson and Walter Brennan as the only male actors with three Oscars -- a feat also achieved by Meryl Streep, Ingrid Bergman, Frances McDormand and Katharine Hepburn, who won four.

Penn has two children with his second ex-wife, the actress Robin Wright.

W.Carter--SFF