Sissy Spacek, 31 Days of Oscar, Day 28

Best Actress. Coal Miner's Daughter (1980)

James Stewart, 31 Days of Oscar, Day 27

Best Actor. The Philadelphia Story (1940). And Lifetime Achievement. (1985)

Audrey Hepburn, 31 Days of Oscar, Day 26

Best Actress. Roman Holiday (1953)

Billy Bob Thornton, 31 Days of Oscar, Day 25

Best Actor. Sling Blade (1996)

Joan Crawford, 31 Days of Oscar, Day 24

Best Actress. Mildred Pierce (1945)

Brad Bird, 31 Days of Oscar, Day 23

Brad Bird. Best Animated Feature. The Incredibles (2004), Ratatouille (2007)

Eva Marie Saint, 31 Days of Oscar, Day 22

Eva Marie Saint. Best Actress - On The Waterfront (1954)

Gary Cooper, 31 Days of Oscar, Day 21

Best Actor, High Noon (1952)

Penelope Cruz, 31 Days of Oscar, Day 20

Best Supporting Actress. Vicky Cristina Barcelona (2008)

William Holden, 31 Days of Oscar, Day 19

William Holden. Best Actor - Stalag 17 (1953)

Greer Garson, 31 Days of Oscar, Day 18

Greer Garson. Best Actress - Mrs. Miniver (1942)

Charlton Heston, 31 Days of Oscar, Day 17

Best Actor, Ben Hur (1959)

Teresa Wright, 31 Days of Oscar, Day 16

Best Supporting Actress. Mrs. Miniver (1942)

Sean Connery, 31 Days of Oscar, Day 15

Sean Connery. Best Supporting Actor - The Untouchables (1987)

Bogart and Bergman, 31 Days of Oscar, Day 14

Humphrey Bogart, Best Actor - The African Queen (1951) And Ingrid Bergman, Best Actress - Gaslight (1944), Anastasia (1946), Murder on the Orient Express (1974)

Clark Gable, 31 Days of Oscar, Day 13

Clark Gable. Best Actor. It Happened One Night (1934)

Betty Davis, 31 Days of Oscar, Day 12

 Two Time Oscar winner.  Dangerous (1935), Jezebel (1938)

Ernest Borgnine, 31 Days of Oscar, Day 11

Ernest Borgnine. Best Actor . Marty, (1955)

Katherine Hepburn, 31 Days of Oscar, Day 10

4 time Best Actress Winner.
Morning Glory (1933), Guess Who's Coming to Dinner ( 1967), The Lion in Winter (1968), On Golden Pond (1981)

Billy Wilder, 31 Days of Oscar, Day 9

6 time Academy Award winner Billy Wilder.

Elizabeth Taylor, 31 Days of Oscar, Day 8

Elizabeth Taylor.  Best Actress, Butterfield 8 (1960) and Who's Afraid of Virginia Woolf? (1966)

Marlon Brando, 31 Days of Oscar Day 7

Marlon Brando. Best Actor On The Waterfront (1954)

and The Godfather (1972)

Vivien Leigh, 31 Days of Oscar Day 6

Two time Best Actress Oscar winner.
Gone With The Wind (1939),  Streetcar Named Desire (1951).

James Cagney, 31 Days of Oscar Day 5

James Cagney. Best Actor 1942 Yankee Doodle Dandy.

Hattie McDaniel, 31 Days of Oscar Day 4

The first African American to win an Academy Award.
Best Supporting Actress for Gone With The Wind, 1939.

Henry Fonda, 31 Days of Oscar Day 3

Best actor, 1981. On Golden Pond and an honorary Oscar for lifetime achievement.

Loretta Young, 31 Days of Oscar Day 2

Best Actress, 1947
Loretta Young.

Ray Milland, 31 Days of Oscar Day1

Going to do a caricature each day of an oscar winner coinciding with TCMs 31 days of Oscar.

The great Ray Milland, Won an Academy Award for Best Actor 1945 for The Lost Weekend.

There are 8 Movies Referenced here..

The Big Clock, The Lost Weekend, Her Jungle Lover, It Happens Every Spring,

The Major and The Minor, Dial M for Murder, Ministry of Fear, The Thing with TwoHeads.