Year-by-Year: 1940s

1940 (great year)

1. Pinnochio
2. The Great Dictator
3. Rebecca
4. The Shop Around the Corner
5. The Foreign Correspondent (this top 5 is great, the top 3 in particular are very interchangeable)
6. Contraband
7. The Thief of Baghdad
8. The Grapes of Wrath
9. Night Train to Munich
10. The Mortal Storm

Best Director: 

1. Charlie Chaplin, The Great Dictator (another great year)
2. Alfred Hitchcock, Rebecca
3. Ernst Lubitsch, The Shop Around the Corner
4. Ben Sharpsteen, Hamilton Luske, Bill Roberts, Norman Ferguson, Jack Kinney, Wilfred Jackson, T. Hee, Pinnochio
5. Unsure; either Michael Powell, Contraband (it's amazing how productive the likes of him and Hitchcock were at the time) or Powell and his collaborators Ludwig Berger, Tim Whelan, the Kordas and William Cameron Menzies for Thief of Bagdhad.

Best Actor: 

1. Laurence Olivier, Rebecca
2. Charlie Chaplin, The Great Dictator
3. James Stewart, The Shop Around the Corner
4. Conrad Vedit, Contraband
5. Henry Fonda, The Grapes of Wrath

Best Actress: 

1. Joan Fontaine, Rebecca
2. Rosalind Russell, His Girl Friday
3. Valerie Hobson, Contraband
4. Margaret Lockwood, Night Train to Munich
5. Margaret Sullavan, The Shop Around the Corner (so interesting how my win is a Gothic Romance lead and the other four are screwball comedy stars)

Best Supporting Actor:

1. John Carradine, The Grapes of Wrath
2. George Sanders, Rebecca
3. Walter Brennan, The Westerner
4. Conrad Veidt, The Thief of Baghdad
5. Frank Morgan, The Shop Around the Corner

Best Supporting Actress:

1. Jane Darwell, The Grapes of Wrath
2. Paulette Goddard, The Great Dictator
3. Judith Anderson, Rebecca
4. Laraine Day, Foreign Correspondent
5. Evelyn Venable, Pinnochio

1941

1. The Maltese Falcon
2. Citizen Kane
3. The Strawberry Blonde
4. Ball of Fire
5. Sullivan's Travels
6. Dumbo
7. The Lady Eve
8. The Devil and Daniel Webster
9. Love Crazy
10. 49th Parallel

Best Director: Orson Welles, Citizen Kane

Best Actor: Humphrey Bogart, The Maltese Falcon

Best Actress: Barbara Stanwyck, The Lady Eve

Best Supporting Actor: Van Heflin, Johnny Eager

Best Supporting Actress: Mary Astor, The Maltese Falcon

1942

1. Casablanca
2. Saboteur
3. Bambi
4. Now, Voyager
5. Yankee Doodle Dandy
6. This Gun for Hire
7. In Which We Serve
8. This Above All
9. Mrs Miniver
10. The Magnificent Ambersons

Best Director: Michael Curtiz, Casablanca

Best Actor: Humphrey Bogart, Casablanca

Best Actress: Ingrid Bergman, Casablanca

Best Supporting Actor: Claude Rains, Casablanca

Best Supporting Actress: Agnes Moorehead, The Magnificent Ambersons

1943(interesting to note how many anti-war/violence films came out this year)

1. The Life and Death of Colonel Blimp
2. Shadow of a Doubt
3. The Ox-Bow Incident
4. Heaven Can Wait
5. Five Graves to Cairo
6. This Land is Mine
7. The Human Comedy
8. The More the Merrier
9. The Silver Fleet
10. Sahara

Best Director: Powell and Pressburger, The Life and Death of Colonel Blimp

Best Actor: Joseph Cotten, Shadow of a Doubt

Best Actress: Teresa Wright, Shadow of a Doubt

Best Supporting Actor: Dana Andrews, The Ox-Bow Incident

Best Supporting Actress: Deborah Kerr, The Life and Death of Colonel Blimp

1944

1. Double Indemnity
2. Laura
3. Henry V
4. Gaslight
5. Arsenic and Old Lace
6. Lifeboat
7. The Way Ahead
8. Going My Way

Best Director: Billy Wilder, Double Indemnity

Best Actor: Fred MacMurray, Double Indemnity

Best Actress: Barbara Stanwyck, Double Indemnity

Best Supporting Actor: Edward G. Robinson, Double Indemnity

Best Supporting Actress: Tallulah Bankhead, Lifeboat

1945 (need to watch Children of Paradise)

1. Brief Encounter
2. A Tree Grows in Brooklyn
3. The Lost Weekend
4. Leave Her to Heaven
5. 'I Know Where I'm Going!'
6. Rome, Open City
7. The Way to the Stars
8. And Then There Were None
9. Spellbound (I've decided I'l also put films I don't really like but are worth a watch on these lists, if I've really no other alternative)

Best Director: David Lean, Brief Encounter

Best Actor: Ray Milland, The Lost Weekend

Best Actress: Celia Johnson, Brief Encounter

Best Supporting Actor: James Dunn, A Tree Grows in Brooklyn

Best Supporting Actress: Someone from A Tree Grows in Brooklyn, for sure. I remember all the ladies making incredibly strong impressions, but I need to recollect who's lead/supporting, and so on. As an alternative, Jane Wyman, The Lost Weekend, is another strong performance.

1946(actually have quite a bit more I want to see from this year, though I have seen The Big Sleep and wasn't a huge fan of it)

1. It's a Wonderful Life
2. The Best Years of Our Lives
3. Beauty and the Beast
4. Great Expectations
5. A Matter of Life or Death
6. A Night in Casablanca
7. The Killers
8. I See a Dark Stranger
9. The Yearling
10. Notorious

Best Director: Frank Capra, It's a Wonderful Life

Best Actor: James Stewart, It's a Wonderful Life

Best Actress: Ingrid Bergman, Notorious

Best Supporting Actor: Harold Russell, The Best Years of Our Lives

Best Supporting Actress: Donna Reed, It's a Wonderful Life

1947(really need some recommendations for this year, though I love/like all the films on this list. I'd say Out of the Past and Ride the Pink Horse seem like two films that'd be up my street. It seems to be a pretty strong year overall though, since I can already craft some pretty nifty lineups with the limited number of films I've seen.)

1. Odd Man Out
2. Miracle on 34th Street
3. Brighton Rock
4. The Ghost and Mrs. Muir
5. Black Narcissus
6. The Secret Life of Walter Mitty
7. Monsieur Verdoux

Best Director: 

1. Carol Reed, Odd Man Out
2. John Boulting, Brighton Rock
3. Powell and Pressburger, Black Narcissus
4. George Seaton, Miracle on 34th Street
5. Norman Z. McLeod, The Secrey Life of Walter Mitty

Best Actor: 

1. Richard Attenborough, Brighton Rock
2. James Mason, Odd Man Out
3. Rex Harrison, The Ghost and Mrs. Muir
4. Edmund Gwenn, Miracle on 34th Street
5. Danny Kaye, The Secrey Life of Walter Mitty

Best Actress: 

1. Gene Tierney, The Ghost and Mrs Muir
2. Hermione Baddeley, Brighton Rock
3. Deborah Kerr, Black Narcissus
4. Natalie Wood, Miracle on 34th Street
5. Maureen O'Hara, Brighton Rock

Best Supporting Actor: 

1. F.J. McCormick, Odd Man Out
2. Harcourt Williams, Brighton Rock
3. Gene Lockhart, Miracle on 34th Street
4. W.G. Fay, Odd Man Out
5. Robert Newton, Odd Man Out

Best Supporting Actress: 

1. Kathleen Byron, Black Narcissus
2. Kathleen Ryan, Odd Man Out
3. Virginia Mayo, The Secret Life of Walter Mitty
4. Edna Best, The Ghost and Mrs. Muir
5. Maureen O'Hara, Miracle on 34th Street

1948 (some serious re-watches/films I have to watch  for my top 10, any recommendations would be appreciated. I really liked Drunken Angel, but I feel a re-watch might benefit it, and I still have not seen The Treasure of Sierra Madre. So this list might change anytime soon)

1. The Bicycle Thieves
2. The Fallen Idol
3. Drunken Angel
4. Oliver Twist
5. The Red Shoes
6. Hamlet

Best Director: Vittorio De Sica, The Bicycle Thieves

Best Actor:

1. Toshiro Mifune, Drunken Angel
2. Takashi Shimura, Drunken Angel
3. Laurence Olivier, Hamlet
4. Ralph Richardson, The Fallen Idol
5. Lamberto Maggiorani, The Bicycle Thieves

Best Actress: Moira Shearer, The Red Shoes

Best Supporting Actor: Alec Guinness, Oliver Twist

Best Supporting Actress: Sonia Dresdel, The Fallen Idol

1949 (very strong year. I still need to see The Quiet Duel)

1. The Third Man
2. The Heiress
3. White Heat
4. Stray Dog
5. Battleground
6. Kind Hearts and Coronets
7. The Small Back Room
8. The Adventures of Ichabod and Mr Toad
9. The Hasty Heart
10. The Passionate Friends

Best Director: 

1. Carol Reed, The Third Man
2. William A. Wellman, Battleground
3. Raoul Walsh, White Heat
4. William Wyler, The Heiress
5. Akira Kurosawa, Stray Dog

Best Actor: 

1. James Cagney, White Heat
2. Toshiro Mifune, Stray Dog
3. David Farrar, The Small Back Room
4. Takashi Shimura, Stray Dog
5. Dennis Price, Kind Hearts and Coronets

Best Actress: 

1. Olivia de Havilland, The Heiress
2. Alida Valli, The Third Man
3. Kathleen Byron, The Small Back Room
4. Ann Todd, The Passionate Friends
5. Patricia Neal, The Hasty Heart

Best Supporting Actor: 

1. Ralph Richardson, The Heiress
2. Alec Guinness, Kind Hearts and Coronets
3. Trevor Howard, The Third Man
4. Orson Welles, The Third Man
5. Edmond O'Brien, White Heat

Best Supporting Actress: 

1. Virginia Mayo, White Heat
2. Joan Greenwood, Kind Hearts and Coronets
3. Miriam Hopkins, The Heiress
4. Margaret Wycherly, White Heat
5. Keiko Awaji, Stray Dog