Well this is the most ambitious thing I've done in a while! There are a few movies in there that didn't actually fare so well at the Oscars (most notably Citizen Kane and 2001), but I couldn't do a classic movie drawing without including them.
Left to Right:
Eliza Doolittle (My Fair Lady), Charles Foster Kane (Citizen Kane), HAL (2001: A Space Odyssey), Gollum (Lord of the Rings), Judah Ben Hur (Ben Hur), T.E. Lawrence (Lawrence of Arabia), Jack Dawson (Titanic), Scarlett O'Hara (Gone With the Wind), Rick Blaine (Casablanca), Vito Corleone (The Godfather), Hannibal Lecter (Silence of the Lambs), Maria Rainer (The Sound of Music), Forrest Gump (Forrest Gump), Salieri (Amadeus)