Clint Eastwood’s Best Roles!

Jeremy Herbert at /Film decided to come up with his list of Clint Eastwood’s 14 Best Roles Ranked. Narrowing down Eastwood’s best roles to just 14 is tough. Before you click over to check out Herbert’s list, here are my top five (using just Herbert’s picks) and a few more that didn’t make his list, but would have made mine.
Harry Callahan from Dirty Harry: This is a pretty easy choice for me. I think Harry is Eastwood’s most iconic and best role. After that the choices become tougher, but for me Dirty Harry is #1.
Josey Wales from The Outlaw Josey Wales: I placed Josey in the second spot, but to be honest I almost placed Blondie aka The Man with No Name at #2. Today Josey gets the edge, but that could change. Wales loses everything but his humanity. And Herbert is right to mention the classic line: “Dyin’ ain’t much of a living, boy.”
Blondie from The Good, the Bad and the Ugly: The movie that made Eastwood an international superstar.
Will Munny from Unforgiven: I applaud Eastwood for having the patience to wait until he was old enough to play the character. Unforgiven doesn’t give us the typical good guy – bad guy movie. Our good guy is a bad guy. There’s no shooting guns out of the bad guy’s hands. Gut shots are slow, painful deaths. There’s no riding off into the sunset with the girl. John Wayne would have hated this film. I wouldn’t want all my westerns to be like this, but I do love me some Unforgiven.
Other Eastwood characters that would have made my list but didn’t make Herbert’s…
- Hogan from Two Mules for Sister Sarah
- Dave from Play Misty for Me
- Ben Shockley from The Gauntlet
- Gunnery Sargent Thomas Highway from Heartbreak Ridge
- Chief Red Garnett from A Perfect World

























































