Vertigo (1958)
Directed by Alfred Hitchcock
Vertigo is often considered Alfred Hitchcock’s greatest work as a filmmaker, but upon initial release, it was attacked harshly by critics and subsequently lost out to the altogether inferior and rather forgettable Gigi at the 1959 Academy Awards. Apparently, the story of a San Francisco cop (James Stewart) who becomes obsessed with an icy blonde-haired woman (Kim Novak) who just happens to resemble the deceased love of his life, did not sit well with moviegoers hoping for a thriller less deviant and subversive. Maybe more than any of Hitchcock’s other films, Vertigo stands up remarkably well. As for Gigi, well, the less said about it the better.

The Treasure of the Sierra Madre (1948)
Directed by John Huston
Despite winning multiple Oscars, including one for Best Director and Best Screenplay, John Huston’s seminal masterpiece managed to lose the best picture Oscar to Hamlet. Granted, Laurence Olivier’s Hamlet is one of the better Shakespeare adaptations, but it simply pales in execution, longevity and emotional impact when compared to The Treasure of the Sierra Madre. Ostensibly, an adventure film about three ne’er-do-wells looking for gold in the Mexican countryside, the film wonderfully explores how people react under pressure. Humphrey Bogart, in one of his most memorably disconcerting roles, plays the paranoid Fred C. Dobbs as a man corrupted and ultimately doomed by his greed.

2001: A Space Odyssey (1968)
Directed by Stanley Kubrick
Arguably, one of the most glaring miscalculations in Oscar history was awarding Best Picture to the musical adaptation Oliver and not to one of the most influential motion pictures of all time, 2001: A Space Odyssey, Stanley Kubrick’s science-fiction masterpiece. The film contains unforgettable images: a jump cut to a space satellite from a shot of a twirling bone; an ape learning the valuable and destructive power of tools; and probably the most iconic image of all, a giant baby hovering over the earth. Kubrick’s philosophical meditation on the meaning and origin of life in the universe is a stunning achievement in design, special effects, mood and narrative experimentation.

Do the Right Thing (1989)
Directed by Spike Lee
Presented with two films representing differing views of the African American experience, the Academy selected the maudlin Driving Miss Daisy as the Best Picture of the year and neglected Spike Lee’s incendiary polemic. Set to the pulsating and hypnotic music of Public Enemy, the film channels issues of racism, class, and the day-to-day struggle for peaceful cohabitation in a neighbourhood filled with contradictory attitudes, hopes and fears. The controversial ending still strikes a chord with audiences, challenging them to consider their own attitude towards race relations. Spike Lee starred, produced, wrote and directed Do the Right Thing, still his most important achievement as a filmmaker.

The Exorcist (1973)
Directed by William Friedkin
Considering what a rarity it is to see horror films nominated for Academy Awards (The Silence of the Lambs being the exception), the fact that The Exorcist managed to snag 10 nominations and won two (Best Screenplay and Best Sound) is an achievement in of itself. Yet, when it came down to award the Best Picture of 1973, the Academy chose The Sting, a light-hearted, depression-era heist film. At the time of its release, The Exorcist became a cultural landmark for the genre and was the first major blockbuster in horror movie history. The story about a little girl’s demonic possession is a rare fusion of classic melodrama and supernatural thriller, imbuing the film with the seriousness and intelligence missing in today’s horror films.