Coogan's Bluff (1968)

IMDb plot summary: Arizona Deputy Sheriff Coogan is sent to New York City to escort an escaped fugitive back for trial.
Directed by Don Siegel. Starring Clint Eastwood, Lee J. Cobb, Susan Clark, and Tisha Sterling.

This is maybe one of the least likable heroes I have seen on screen in recent memory. Toward the end, when he is confronted about how he hurt someone and responds by going back to hurt them again, I thought, "Surely we MUST be meant to see him as the villain, right? This is too over-the-top for us to not!" But no luck, as his doubling down on his hurtful actions gets him both the criminal he's been chasing AND, apparently, the love of the woman who tried to call him out in the first place. (That last moment actually made me exclaim out loud, "DON'T go back to him, he's reprehensible!") I can't in a million years root for this character, and that makes the rest of this movie, which I think *is* trying to set him up as admirable, a really unpleasant watch.

How it entered my Flickchart:
Coogan's Bluff < An American in Paris
Coogan's Bluff < Persona
Coogan's Bluff < Playtime
Coogan's Bluff > Head
Coogan's Bluff < Shalako
Coogan's Bluff < Susannah of the Mounties
Coogan's Bluff > Attack of the Crab Monsters
Coogan's Bluff > The Good German
Coogan's Bluff > Tuck Everlasting
Coogan's Bluff > Harold & Kumar Go to White Castle
Coogan's Bluff < Broken Flowers
Final spot: #2886 out of 3127.