The 10 Highest-Grossing Sean Penn Movies. Ranked

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Sean Penn first began performing in television before moving to New York City in the 1980s to pursue a career in movies. He starred in several Off-Broadway performances that showed versatility, and critics noticed his work. In the early 1990s, Penn diversified his portfolio and branched out in the fields of producing and directing. He earned his first Academy Award nomination in 1995 and won his first Academy Award in 2004. The actor has continued working in drama and action movies and received several awards, including a Cannes Best Actor, a Golden Globe, a SAG Award, a Critics’ Choice Award, and an Honorary César.

As one of the most respected actors in Hollywood, Sean Penn has starred in over a hundred projects throughout his career and continues to contribute to the cinema with his work in feature films and documentaries. Let’s take a look at his highest-grossing movies.

The Tree Of Life (2011)

Directed by Terence Malick, The Tree Of Life is an art film that chronicles the meaning of life throughout the various ages of aging. According to Screen Rant, Penn portrays the role of Jack O’Brien as an adult who finds it difficult to adjust to the world of modern materials. The movie starred Brad Pitt, and Jessica Chastain grossed $61.7 million worldwide.

The Game (1997)

A critical triumph, David Fincher has never disappointed with his psychological crime thrillers. The movie collected $80.3 million in theatres against a $70 million budget. The Game saw Sean Penn plays the role of Conrad van Orton, the younger brother of the lead character played by Michael Douglas. A sequence in the film is noted as one of the 100 Scariest Movie Moments.

Dead Man Walking (1995)

A film based on a true story, Dead Man Walking stars Sean Penn and Susan Sarandon in leading roles that earned them Oscar nominations, and Sarandon won in her category. In the film, Penn is a convicted death row murderer who is counseled by Sarandon’s character of a merciful nurse as his execution date approaches. The movie made $83 million worldwide.

I Am Sam (2001)

A heartbreaking movie in every shape and form, I Am Sam remains one of Sean Penn’s most memorable performances. The film earned Penn an Oscar nod and collected $92.5 million against a $22 million budget. The actor played the lead role of Sam Dawson, a mentally challenged parent fighting to get his child’s custody, as reported by Collider. The movie gained critical acclaim and launched the career of young actress Dakota Fanning.

The Thin Red Line (1998)

Sean Penn and Terence Malick’s first collaboration, Thin Red Line, is a World War epic that stars a string of A-List actors, including George Clooney, Adrien Brody, and John Travolta, with Sean Penn in the leading role as First Sergeant Edward Welsh. The film was a moderate success at the box office and made $97.9 million on a $52 million budget.

Gangster Squad (2003)

Gangster Squad is an action thriller based on the fictionalized version of real-life LAPD officers who were called the Gangster Squad. Penn is the most powerful mobster in LA and the leader of the Squad. The movie grossed $104.1 million and starred Josh Brolin, Anthony Mackie, Ryan Gosling, Emma Stone, and Nick Nolte.

Mystic River (2003)

Sean Penn won his first Academy Award as a Lead Actor in the Clint Eastwood-directed Mystic River. As mentioned by Esquire, his performance in the movie is cited by New York Times as one of the most definitive portrayals in the last half-century. Playing the character of a dead girl’s father, the movie touched audiences and earned $156.8 million worldwide.

The Interpreter (2005)

The Interpreter is a unique political thriller. It was the first film allowed to shoot inside the United Nations Headquarters. It is the last film by acclaimed director Sydney Pollack before passing away in 2008. Starring Sean Penn and Nicole Kidman in lead roles, it made $162.7 million worldwide.

The Secret Life Of Walter Mitty (2013)

Adapted from the short story by James Thurber, The Secret Life Of Walter Mitty grossed $187.8 million in total and has earned a cult following since its release. The adventure and comedy movie follows the life of an opposing assets manager Walter Mitty played by Ben Stiller, the movie's director, as stated by IMDB. Penn played the supporting role of Sean O’Connell, a photojournalist.

The Angry Birds Movie (2016)

Sean Penn forayed into new territory when he performed voice acting in a computer-animated film, The Angry Birds Movie. He lent his voice to the character of Terence, who grunts and growls. It remains one of his highest-grossing movies as it garnered $352.3 million in theatres worldwide.

Sean Penn has portrayed several critically acclaimed roles in movies over the years. His Lead Role in Milk earned him his second Oscar, while his other movies, 21 Grams and Colors, are also his well-appreciated roles. Penn is also a documentary director and was recently in Ukraine filming the Russian invasion in the country before returning to America.

Sources: Screen Rant, Collider, Esquire, IMDB