Planning to watch every Oscar best picture winner

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Which should I look forward to most or which are they worst I should dread?

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Depends on which ones you've seen.

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which are they worst I should dread?

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Crash
Birdman
American Beauty
English Patient
Moonlight
Shape of Water

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Which should I look forward to most

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The Lost Weekend (underrated)
Bridge on the River Kwai
Lawrence of Arabia
Amadeus
The Sting
A Man for All Seasons
Waterfront
Etc.

Gone with the Wind, Casablanca if you've never seen those. I mean, they did get most right up to about 2002 or 3 or so, then it starts to get weird. So most prior to that year are all legitimately great movies, save a handful.

There's some real crap peppered throughout the winners of the 30s and 40s. To complete this task, I would do a rotation of newer winners that interest you, well-regarded movies from decades you're not familiar with, and the early ones that look like garbage to you.

If you start with and finish all the ones that interest you now, the rest could become a chore.

Birdman seems to get a lot of hate round here. I enjoyed it.

Forget about '71 winner The French Connection and go instead with nominee The Last Picture Show, the real picture of the year.

Winners and worth watching 1927 until 1939

27 Wings
28 The Broadway Melody
29-30 All Quiet on the Western Front
The scene in the grave yard has yet to be equaled on film
Disraeli is worth watching
31 Cimarron
32 Grand Hotel maybe the weakest of the early winners
33 Cavalcade
should have I am a Fugitive from a Chain Gang have won?
34 It Happened One Night this is the year the 30's start showing why it was the best decade in movie making in the US
Cleopatra
Thin Man
Imitation of Life
35 Mutiny on the Bounty
Captain Blood
Les Misérables
The Lives of a Bengal Lancer
36 The Great Zigfeld
37 The Life of Emile Zola
Captain Courageous
Lost Horizon
38 You Can't Take it with You
The Adventures of Robin Hood
Grand Illusion
39 Gone With the Wind
Goodbye Mr Chips
Ninotchka
Beau Geste
Stagecoach
Mr. Smith Goes to Washington
The Wizard of Oz
1939 is the strongest year overall for films made in the US. The above is just part of a long list of good movies.

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Both decent, but Best Picture? Yeah, no.

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I think it's healthier to look at best picture winners as a snapshot of Hollywood, and nothing more. It's unlikely that what they vote for will ever fully align with your (I mean anyone's) taste. I love paying attention to the Oscars because I love watching movies, but I can't actually assign any value to them and the movies they choose to nominate. It's a literal popularity contest, as made explicit in the first ceremony's division of film and "artistic picture". It's that distinction that's made winners like Moonlight and Parasite so weird and unique.

I think Casablanca, The Apartment, The Godfather, and Unforgiven are the only best picture winners that actually top my best of the year lists from their respective years.

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Forget about '71 winner The French Connection and go instead with nominee The Last Picture Show, the real picture of the year.

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Dude... I'm fan of Last Picture Show and all, but The French Connection is one of the best crime films and most revolutionary productions in cinema history. It paved the way and look for all the gritty 70s crime/NY films. It's also entertaining as hell and the acting is stellar... I think it's one of my 10-15 favorite movies.

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you'll find out that most Best Picture winners are actually fricking terrible movies.

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Most? Let’s calm down