Acting & Activism: Sean Penn is a Rebel With A Cause


[Sean Penn at the 2008 San Francisco premiere for the film Milk]

A Star Is Born

On August 17, 1960, Sean Justin Penn was born to actor and director Leo Penn and actress Eileen Ryan. From his parents, he learned to value both the creative process and the rights of the individual.  During the McCarthy Era, his father’s successful film career was cut short when he was branded a Communist and blacklisted after refusing to “name names” to the Un-American Activities Committee.

Leo’s integrity and loyalty was firmly imprinted on young Sean when the father and son visited the film set of The Last Tycoon [starring Robert De Niro and Jack Nicholson].  The film’s director, Elia Kazan, was heard singing the praises of Leo Penn and Leo, who was known as a warm and genial sort, walked right by, ignoring Kazan.  You see, Kazan HAD named names and Leo was not interested in consorting with him.  The incident resulted in the concept of artistic and personal integrity, over success and celebrity, being indelibly implanted on Sean.

Spicoli, The Falcon & The Snowman

Growing up in the Los Angeles area, Sean made friends with the likes of future stars Emilio Estevez, Charlie Sheen and Rob Lowe, but Sean’s career trajectory was not to be found in the frothy Brat Pack films that would earn his friends their celebrity.  Sean’s interest was always in offbeat roles and films, although his first breakout role was that of surfer dude and party king, Jeff Spicoli, in 1982’s Fast Times at Ridgemont High, in which Penn stole the film and created buzz.

The “serious” film crowd took notice and Penn answered the call by starring in the crime drama Bad Boys. His portrayal of troubled youth Mick O’Brien gained him critical acclaim. This role also marked the beginning of Penn earning a reputation for devotion to his craft, as his research had included him spending time on the job with the Chicago police crimes unit.

[Promotional poster for The Falcon & The Snowman]

In 1985, Penn’s acting career took yet another major leap forward as he starred in the espionage drama The Falcon And The Snowman [based on a true story] . His performance in the role of U.S military secret-seller Andrew Daulton Lee was breathtaking [this was the first film I saw Penn in and it made me a fan for life] and again Penn was lauded as an outstanding young actor.

The longterm affects of Penn’s portrayal of Lee was not only on his film career. Lee, who had been convicted of espionage, was paroled in 1998. In an interview in 2005, it was stated that Penn later hired Lee as his personal assistant, partly because he wanted to reward Lee for allowing him to play Lee in the film, and also because he was a firm believer in rehabilitation and thought Andrew Lee should be successfully reintegrated into society since he was a free man again.  Leo Penn’s life lessons were becoming an integral part of Sean Penn’s life.

Living In A Material World

1985 was also the year in which Sean Penn married the mega pop star Madonna. The unlikely union of reticent movie star and attention-loving songstress had serious and unwanted results. During the four years of the marriage, Penn became as famous for his angry outbursts against the paparazzi, as for his acting.  Penn had always had an uneasy relationship with the press, but the intense media attention surrounding his marriage sent Penn railing against the photographers who constantly pursued him and his wife. Amongst the incidents, he was notably arrested and sentenced to jail for assaulting a photographer in 1987.  Madonna and Sean Penn ended their volatile union by divorcing in 1989.

Dead Man Walking

While recovering from the conflict of the Madonna years, Penn continued his successful film career, with critically acclaimed turns in Brian de Palma’s 1989 feature Casualties of War and 1990’s State of Grace.

Penn also tried his hand at screenplay writing and directing in 1991.  His star-studded feature The Indian Runner was well received and was a fulfilling experience for Penn.

The ’90’s were a prolific career period for Penn – he was nominated for 3 Golden Globe awards [Carlito’s Way, Dead Man Walking, Sweet and Lowdown] and received 2 Academy Award nominations for Best Actor [Dead Man Walking, Sweet and Lowdown]. He won the Independent Spirit Award for Best Male Lead for his role in Dead Man Walking.

Acclaimed Actor/Director, Beleaguered Activist

The new Millennium was a watershed time for both for Sean Penn’s career and his activism.

In 2001, he was nominated for an Academy Award for Best Actor, a BAFTA for Best Actor and a Screen Actors Guild Award for Leading Male for his touching portrayal of a mentally-challenged father in I Am Sam . His honesty in the role was credited to him researching the part by spending time at Los Angeles’ GOAL Center, where he befriended developmentally disabled adults – two of the centre’s residents were even given roles in the film.

2003 brought Penn’s first Oscar win – for Best Actor in the heartrending mystery Mystic River.

In 2007, Penn was nominated for several awards for both screenwriting and directing, for his feature Into The Wild.

2008 saw him win his second Best Actor Oscar for the role of slain gay rights leader, Harvey Milk. In place of the usual “gratitude” acceptance speech, Penn said “…I think that it is a good time for those who voted for the ban against gay marriage to sit and reflect and anticipate their great shame and the shame in their grandchildren’s eyes if they continue that way of support. We’ve got to have equal rights for everyone!”


His first foray into activism came in 2002 – he visited Baghdad, Iraq because he did not, he said, accept the government’s spin on the situation following 9/11 and was following EL Doctorow’s advice that it is “the responsibility of the artist to know the time in which he lives”.

Penn subsequently took out a 56,000$ ad in The Washington Post to feature an open letter he wrote to U.S. President George W. Bush in which Penn criticized the planned attack on Iraq, The War On Terror and the “deconstruction of civil liberties.” The letter was scathing and in it, Penn asked for the impeachment of President Bush and also called Bush, Vice President Dick Cheney, and Secretary of State Condoleezza Ric “villainously and criminally obscene people.”  Penn received both support and scathing criticism for his stance, but he was unwavering in his convictions and continued to protest the Iraq war, The War on Terror and the loss of civil liberties throughout the Bush Presidency.

[Sean Penn in New Orleans, 2005]

In September 2005, in the aftermath of Hurricane Katrina, Penn travelled to New Orleans, Louisiana to assist with relief efforts.  He was filmed physically assisting flood victims – feats that were both lauded and maligned – Penn was ridiculed for being attention-seeking and silly.  But Penn got his message across via the massive media exposure – that the US government’s failure to respond swiftly to the disaster was resulting in tremendous loss of life and livelihood.

[Sean Penn in Haiti]

In 2010, one week after a 7.0 earthquake devastated Haiti, Penn travelled to the stricken country to help.  The unfathomable loss of life led him to co-found the  J/P Haitian Relief Organization, which has been running a 55,000 person tent camp overseeing 11,000 tents, medical personnel, a market and food dispersement. He helps funds fledgling schools, evaluating each and greeting fleetingly excited children personally. He even fights gangs, which overwhelm the country in many places.  In July of 2011, Penn told CBS “There’s something that takes over and it’s really an obligation because you see the strength of the people who have never experienced comfort, and the gifts that that can give to people like myself and to our country and culture. You see the enormous gaps.”

Sean Penn is still in Haiti and has said that he will stay there indefinitely.


As Sean Penn has said “Your life is what you bring to any story. This is a life craft. It`s “How do you feel? Who are you? What do you have to say?”


Sean Penn has been called “humourless”. I’m not so sure…Watch Sean on “Between Two Ferns with Zach Galifianakis”: