Welcome to 5 Favorites. Each week, I will put together a list of my 5 favorites (films, performances, whatever strikes my fancy) along with commentary on a given topic each week, usually in relation to a specific film releasing that week.

Sean Penn may have started his acting career in fluff roles in films like Fast Times at Ridgemont High and Taps, but his career took a decidedly impressive twist as the 1980s turned into the 1990s. His first pinnacle came with his Oscar-nominated performance as a death row inmate in Dead Man Walking. His second pinnacle was more of a plateau lasting from Mystic River in 2003 to Milk in 2008, a five-year period in which he won two Oscars for acting. As a director, however, his work has been less than spectacular with Into the Wild being the only film to stand out amongst his filmography. This week, his latest self-directed starring vehicle, Flag Day, releases in theaters, so I thought I would give a run down of my five favorite films featuring Sean Penn.

Dead Man Walking (1995)

As Matthew Poncelet, Penn shows a level of maturity as an actor that his prior efforts had only hinted at. The gruff, penitent death row prisoner provided him the kind of nuanced character he could sink his teeth into and ultimately delivered one of this best performances to date. His co-star is Oscar winner Susan Sarandon as Sister Helen Prejean who grows closer to the convicted killer while simultaneously empathizing with his victim’s families.

Actor Tim Robbins had only directed one film previously, the modestly successful Bob Roberts, but his ability to get the audience in close with a convicted killer and make his search for salvation a compelling drama, worked incredibly well for him and his stars. The film scored four Oscar nominations, but not one for Best Picture. It’s a great film that asks us to try and see life and loss from two sides even if it’s not convenient.

The Thin Red Line (1998)

Terrence Malick’s war masterpiece The Thin Red Line featured Sean Penn in a role that wasn’t particularly important as the film was more concerned with presenting the horrors and atrocities of war than it was with providing a coherent narrative. It was a film that divided audiences with some hailing it as a masterpiece and others finding it dismissive and dull. I fell on the side of masterpiece.

Although it’s an adaptation of James Jones’ autobiographical novel surrounding the conflict at Guadalcanal during World War II, the film is a meditation on death, nature, and the cycle of life. While we may seem as distant observers, watching as life meets death in the midst of the wilds of the world, we’re forced to contemplate whether we are merely animals acting out of instinct or the higher forms of life we so often claim to be. It’s a deep, complex film that might not be narratively dense, but it’s thematically and visually resplendent.

Mystic River (2003)

Having made numerous successful films over the course of a storied career, Clint Eastwood had diverged from the quality-conscious efforts of Unforgiven and The Bridges of Madison County, for several years before returning to a slate of thematically challenging and narratively complex series of films in the early-to-mid 2000s. This was the first in that series that led to his second Oscar the following year and more Oscar nominations for his films over the subsequent years.

Mystic River was about three childhood friends who must contend with the trauma one of them had gone through so many years earlier. A riveting mystery unfolds as we slowly become aware of the details surrounding the events and how they came to destroy the lives of everyone involved. Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, and Laura Linney all deliver powerhouse performances in a film that might well be the best acting ensemble gathered in Eastwood’s impressive directorial career.

21 Grams (2003)

In 21 Grams, Penn stars as a critically ill mathematician who finds his life intertwined with a grieving mother (Naomi Watts), and a born-again ex-con (Benicio del Toro). The three deliver strong performances in Alejandro G. Inarritu’s English language feature debut, his second film, and predecessor to his more widely recognized Babel and years before his Best Picture winner, Birdman. The astute screenplay by Guillermo Arriaga follows these three characters as they interact over a tragic car accident.

Milk (2008)

As the 2000s drew to a close, so too did Penn’s illustrious string of successes. Milk might well have been his greatest acting triumph yet. The film, about California’s first openly gay elected official recounts the rise of tragic assassination of one of the most notable gay figures in American history: Harvey Milk. The film co-stars Emile Hirsch, Josh Brolin, Diego Luna, James Franco, Alison Pill, Victor Garber, and Denis O’Hare in a poignant biopic that expresses the importance of representation in government.

Gus Van Sant, who didn’t come out publicly until well after the film was released, and screenwriter Dustin Lance Black were the perfect gay artists to bring this story to the big screen. Van Sant’s output has been mediocre at best, but with this effort, he put together a fine film with great performances. Although Penn himself isn’t gay, his portrayal of Harvey Milk was impressive and deserving of the Oscar it received.