One of the earliest war movies in history, “Wings” became the very first film to win the Academy Award for Best Picture. 1920s mega-star Clara Bow played the love interest of two air combat pilots (Richard Arlen and Buddy Rogers) in World War I. The film impressed audiences for its unbelievable aerial sequences, a major feat for the earlier days of cinematic technical prowess. Gary Cooper played a small role in the film, which led to him becoming one of Hollywood’s biggest stars.

Gary Cooper leads in this tale of an incredible sniper, Alvin C. York, who becomes a World War I hero when his marksmanship forces a German platoon to surrender. Cooper’s acclaimed performance not only won the Oscar for Best Actor—and earned 11 total nominations including Best Picture—it led to the American Film Institute naming York as the 35th greatest hero in American film history.

The second James Jones story to make the list—see #33, “From Here to Eternity” starred Burt Lancaster, Montgomery Clift, and Frank Sinatra as soldiers stationed in Hawaii in the months before the Pearl Harbor attack. It ended up winning eight Oscars in 1954 and has since been added to the National Film Registry for its tremendous cultural significance. It was Sinatra’s only Academy Award win for his acting work.

At almost four hours long, “Gone with the Wind” is a sprawling epic film about the downfall of a well-to-do southern family. Set in Georgia during the Civil War, the adaptation of Margaret Mitchell’s 1936 novel set all kinds of box office records. Clark Gable and Vivien Leigh starred in the picture that eventually took home 10 Oscars in 1940, including Best Picture, Best Director, Best Writing, and Best Actress in a Leading Role. AFI listed it as #6 on a list of best American movies of all time.

Denzel Washington won his first Oscar for his role in this Civil War film about one of the first all-black regiments in American history. Matthew Broderick plays Captain Robert Shaw, a white colonel in charge of a group of black volunteers for the Union Army. The group deals with racism and prejudice within their own army as they fight against the Confederacy and the evils of slavery on the other side. The film enjoyed massive critical success: New York Times film critic Vincent Canby called the cast “superior” and correctly predicted that Washington was “on his way to a major screen career.”