2. Milk (2008)

A year after directing “Into the Wild,” Sean Penn returned to true-life terrain, this time in front of the camera in “Milk,” Gus Van Sant’s bold biopic of Harvey Milk, a gay rights activist and the first openly gay politician to be elected into public office in the state of California.

While “Milk’s” story has all the elements of a great screenplay—a compelling protagonist, a struggle in overcoming adversity, a series of tenuous relationships (both romantic and professional) and an untimely ending—it took more than a decade for the film to come together.

Its eventual big-screen mounting is from a script by Dustin Lance Black, an LGBT activist who was inspired by “Milk’s” story after seeing Rob Epstein’s acclaimed documentary, “The Times of Harvey Milk,” while in college.

Black dedicated three years of his life researching the script, which he wrote on spec. The result was a film that connected with people in a universal way, including Penn (who won an Oscar for the role), who related to “Milk’s” outspoken nature when it comes to fighting for one’s beliefs.

Appropriately, the film’s release coincided with California’s 2008 vote on Proposition 8, which eliminated the state’s recognition of same-sex marriages.