In 1973, I was eleven years old and my brother was nine. We had just seen ‘The Poseidon Adventure’, and were very excited to see it pop up on the Oscar Nominations, and so stayed up to watch the entire broadcast together. We have continued the tradition every year, and, even when we moved away from home, miles away from each other, we would still call up and compare notes every year during the show.

My brother has thrown an “Oscar Party” either at his home or at his restaurant in Chicago, for longer than I can remember, and since 2005, I’ve commemorated each party by creating a ‘caricature poster’ that includes each of the acting nominees, best picture nominees (and often directors and animated features). Above is the most recent entry for 2019, and the first one I’ve done in a couple years (I only got as far as a rough sketch for 2017, and completely missed 2018). Below are the previous posters (mostly they are in black and white, but I broke out of the format in 2009 with a ‘3-D Poster’ and again in 2011 with a full color poster).

I have backdated a few when I’ve gotten ‘in the zone’ some years, and couldn’t stop with just one poster, so 2004 was actually drawn in 2015, and in 2019 I got on a roll and completed 1973, 1974 and 1975 as well as the 2019 poster.

I have been dating the posters as to the year of the ceremony, so that an oscar poster dated 2007 is actually portraying the movies from 2006 (these dating conventions change depending on your source, or who you talk to). I have placed the samples below in the order of the year depicted, however, some of them were drawn the same year, and others were ‘backdated’, and I have indicated which year they were drawn.

1973 (drawn in 2019): The Godfather, Cabaret, Deliverance, Sleuth, Lady Sings the Blues, etc
1974 (drawn in 2019): The Exorcist, The Sting, Paper Moon, Save the Tiger, etc
1975 (drawn in 2019): The Godfather Part II, Chinatown, Lenny, Alice Doesn’t Live Here Anymore, A Woman Under the Influence, etc
2004 (drawn in 2015): The Lord of the Rings: Return of the King, Mystic River, Cold Mountain, etc
2005: Million Dollar Baby, Ray, Closer, Sideways, The Aviator, Hotel Rwanda, etc
2006: Capote, Crash, Ring of Fire, Brokeback Mountain, Transamerica, etc
2007: The Queen, Amin, The Devil Wears Prada, Little Children, Little Miss Sunshine, Babel, etc
2008: Juno, There Will Be Blood, Elizabeth, No Country for Old Men, Michael Clayton, etc
2009: Frost/Nixon, The Wrestler, Milk, The Curious Case of Benjamin Button, etc
2010 (in 3-D): Avatar, Precious, Inglorious Basterds, An Education, Up in the Air, etc
2011: The King’s Speech, Black Swan, True Grit, The Social Network, The Kids Are Alright, etc
2012 (painting, in color): Moneyball, Marilyn & Me, The Help, The Artist, War Horse, etc
2013: Lincoln, Les Miserables, Silver Linings Playbook, Flight, Life of Pi, etc
2014: Nebraska, American Hustle, Blue Jasmine, The Wolf of Wall Street, etc
2015: Birdman, The Imitation Game, The Theory of Everything, Selma, etc
2016: Mad Max Fury Road, The Revenant, Carol, The Martian, The Big Short, etc
2019: A Star is Born, Bohemian Rhapsody, Black Panther, BlacKkKlansman, Roma, Vice, etc