Two-time Academy Award winner Sean Penn has become an American film icon in a career spanning over three decades.

Penn has been nominated five times for the Academy Award as Best Actor for Dead Man Walking, Sweet and Lowdown, I Am Sam and won his first Oscar for his searing performance in Clint Eastwood's Mystic River and his second Oscar as Best Actor for Gus Van Sant's Milk. The performance as gay rights icon Harvey Milk also garnered Penn "Best Actor" awards from The Screen Actors Guild, New York Film Critics Circle, and Los Angeles Film Critics Association.

Penn's feature film directorial debut came with The Indian Runner, which he also wrote and produced. He directed The Crossing Guard, which he also wrote and produced. His third film as director/producer was The Pledge. Penn later wrote and directed the United States contribution to the compilation film 11'09'01. This important project gathered 11 acclaimed directors from around the world to create short films in response to the horrific events of September 11, 2001. As a writer, producer, and director, Into the Wild marked Penn's fourth feature film, which opened to rave reviews. The film garnered two Academy Award nominations and nominations from the DGA and WGA for Penn.

Penn has appeared on stage in productions including Alfred Hayes' Girl on the Via Flaminia and Albert Innaurato's Earthworms In Los Angeles. On Broadway, Penn performed in Kevin Heelan's Heartland and John Byrne's Slab Boys. He appeared in David Rabe's Hurlyburly, at the Westwood Playhouse, and Goose and Tom Tom, at Lincoln Center, both productions directed by the author. Additionally, Penn starred in The Late Henry Moss, written and directed by Pulitzer Prize-winning writer Sam Shepard.

Sean Penn was presented with the Modern Master Award at the Santa Barbara International Film Festival and became the youngest recipient to ever receive the Donostia Lifetime Achievement Award from the San Sebastian Film Festival. He has been honored with the John Steinbeck Award for outspoken torch-bearers in the creative arts and the Desert Palm Achievement Award for Acting, after being presented with the Director of the Year Award for Into the Wild from the Palm Springs International Film Festival. Penn served as President of the jury for the Cannes International Film Festival and later that year was named a Knight in the French Legion of Honor.

As a journalist, Penn has written for TIME, Interview, Rolling Stone, and The Nation magazines. Penn's landmark interviews with Venezuelan President Hugo Chavez, and Cuba's President Raul Castro, was President Castro's first-ever interview with an international journalist. Penn’s latest story for Rolling Stone found him in the jungle of Mexico interviewing then at large drug lord Joaquin “El Chapo” Guzman Loera prior to his most recent capture by the Mexican authorities.

Penn's humanitarian work found him in New Orleans in the immediate aftermath of Hurricane Katrina and more recently in earthquake-ravaged Haiti. Penn established the J/P Haitian Relief Organization (J/P HRO). Today the organization employs a predominantly Haitian staff of over 350 professionals to support families in areas affected by the earthquake transition to resilient, sustainable, and prosperous communities.

For his efforts, Penn has received numerous honors and awards, including the Stanley Kramer Award from the Producers Guild of America and the Children's and Families Global Development Fund Humanitarian Award. Penn was knighted by Haitian President Rene Preval in a ceremony in Port-Au-Prince. He was also presented with the Peace Summit Award at the 12th World Summit of Nobel Peace Laureates, a tribute for extraordinary solidarity by the Haitian Parliament in a combined meeting of the National Assembly and the International Humanitarian Service Award from the American Red Cross.