I'll make a few stray comments I guess.
69. Pink Cadillac - I don't get the hatred for this. I can see Eastwood fans giving it a fair chance and still not liking it, but it is a personal and thematically coherent movie rather than a complete mess. The villains are a white power militia so maybe people will start thinking that it's cool to like this one.
56. Firefox - This is the kind of movie where I agree with all the points made in an auteurist analysis of why it's classic Eastwood but unlike Pink Cadillac it doesn't translate to me enjoying it all that much.
46. Sudden Impact - One of his better genre films and should be higher. B.D. hates it though.
45. Midnight in the Garden of Good and Evil - One of his most ambitious. I'm a fan, but it never pleased Dirty Harry fans or fans of the book.
43. The Eiger Sanction - a real mess, should be toward the bottom.
37. Joe Kidd - I've never seen this but it's supposed to be pretty bad and a major disappointment from a Clint Eastwood/John Sturges collaboration. Actually I don't think Sturges' later stuff is supposed to be very good. Anyway surprised to see it right above The Gauntlet and Space Cowboys, too good movies I'd think most of people who liked Eastwood for both high and low brow reasons would enjoy.
36. The Enforcer - least interesting Dirty Harry movie
33. Changeling - pretty close to being genuinely bad, he took over it at the last minute and it's full of part that remind you that it's a Clint Eastwood for this or that reason like he was scrambling to put his mark on it but instead just making a mess.
30. Heartbreak Ridge - I think this one is underrated and light years more engaged and entertaining than American Sniper, so seeing it this high is one of the lists few pleasant surprises.
29. Invictus - one of his flattest and most boring. The heroes are well cast but they're too flawless, at least in context of this story, for Eastwood to sink his teeth into them.
25. A Perfect World
24. White Hunter, Black Heart - Two of his best, should be even higher.
20. In the Line of Fire - there's know huge crippling flaw to make me think it's truly bad but this one is just a commercial cash in that I've never wanted to revisit.
14. American Sniper - right before the list gets good with some recognition for Bird at #13, this is a pretty toothless and anonymous movie given its massive commercial success and avalanches of controversy.