best film:   The Good, The Bad, and The Ugly (1966) from the great Sergio Leone is the strongest of the “Dollars” or “Man with No Name” trilogy and that is a accomplishment in itself. A Fistful of Dollars (essentially a Yojimbo remake) and For a Few Dollars More are brilliant works – making this sneaky candidate for the all-time finest trilogy in cinema history nominee. These are superbly stylized films by Leone – and Eastwood is the steady hand (and a straight up blow your hair back revelation in the first film) in the lead. Beyond the work with Leone, Unforgiven is a masterpiece and Million Dollar Baby is not far behind. These two are directed by Clint as well of course. This leaves Don Siegel’s finest film Dirty Harry as the sixth entry that Eastwood has been really stellar in that is either at the must-see or the masterpiece level.


In three short years from 1964 to 1966 (The Good, the Bad, and the Ugly here) the Sergio Leone and Clint Eastwood collaboration put its historic stamp on both the western genre and 1960s cinema.


best performance:  Unforgiven by the smallest of margins over A Fistful of Dollars, The Good, The Bad, and The Ugly and Million Dollars Baby. Eastwood’s physical (largely silent) performances in the first and last leg of the Leone western trilogy are justifiably iconic. Million Dollar Baby is not a wrong answer either and it could be the best of his career (quite a feat at age 74). This film is loaded with great acting from both Morgan Freeman and Hilary Swank as well. Ultimately, Unforgiven just seems to combine the best of the other options. It has some of the silent, physical screen presence “Eastwood as Western icon” (a la John Wayne) moments like he did so well in his work with Leone – but – it also has some more tender moments like his few moments with his children, the moments with the prostitute who mends his wounds, and of course, the dazzling soliloquy under the tree to the Schofield Kid actor Jaimz Woolvett.


Eastwood has been a bankable star since the 1960s – but there were peaks and valleys in that career and there were more valleys in the 1980s than one would like to see from an actor of Clint’s caliber. So, Unforgiven in 1992 was his comeback film and in many ways was supposed to be his swan song (look at how wrong that turned out to be). Eastwood triumphs as William Munny – the reformed man with a dark past.


stylistic innovations/traits: Eastwood’s career is pretty easy to break down in phases. He has twenty (20) films in the archives as actor. He starts off with those three (3) landmark films with Leone in the 1960s but just pause here for a minute. He starts off his career with an impressive lead turn two must-see films and then a masterpiece (and top 100 all-time level masterpiece) in his first three archiveable films in a three year span. This is unreal and frankly most actors on this list cannot catch up to that start. After leaving Italy and Leone, he connects quickly with the talented workman Don Siegel for four (4) archiveable films in the 1970s. That is four big films and several rock solid second and third tier (The Beguiled  is fascinating) before 1980 (more than a decade from his best performance and two decades from Million Dollar Baby). During that same stretch with Siegel starting in the early 1970s Eastwood becomes a director himself (clearly a gifted director). He would go on to have more more archiveable films as a director than Leone and Siegel combined and though there were some misfires, when it was all said and done Eastwood proved himself to be one of the best 100 directors of all-time. Eastwood is not a versatile actor – without a doubt, he is not known for his chameleon-like range or for disappearing into a character. He played bounty hunters, outlaws, cops, sheriffs – tough as nails, often violent, no BS – often in westerns or the crime genre (he played Harry Callahan five times). Eastwood is a large scene presence though (like Humphrey Bogart or John Wayne before him). But still, through the years when Eastwood did collaborate with actors with more range (from Eli Wallach to Gene Hackman to Jeff Bridges to Morgan Freeman to Meryl Streep) – Eastwood hangs right there with them just fine (and better in some cases). It would be a fun study to compare his acting career and accomplishments with John Wayne. Eastwood emerged as an actor in the 1960s and beyond during an era where method and range were considered more important traits for a great actor – but Clint’s filmography matches and exceeds many of the best of the same era even during the The New Hollywood era in the 1970s (many would be thrilled to have In the Line of Fine as their tenth best performance).


Eastwood as the titular character in Don Siegel’s Dirty Harry in 1971. Those expecting a point and shoot cinematically flat crime film will leave the film blown away by some of the stylistic flourishes veteran director Don Siegel has up his sleeve. And Eastwood is a force as the cop in pursuit of a Zodiac-like killer (Andrew Robinson) in San Francisco.


directors worked with:  Clint Eastwood (10), Don Siegel (4), Sergio Leone (3), Michael Cimino (1) – a shorter list here because he directed himself so many times of course.


Forty (40) years after A Fistful of Dollars – Eastwood delivers another banner film and performance in Million Dollar Baby. 


top five performances:

  1. Unforgiven
  2. The Good, The Bad, and the Ugly
  3. A Fistful of Dollars
  4. Million Dollar Baby
  5. Dirty Harry


archiveable films

1964- A Fistful of Dollars
1965- For a Few Dollars More
1966- The Good, The Bad, and the Ugly
1968- Hang’em High
1970- Two Mules for Sister Sara
1971- Dirty Harry
1971- Play Misty for Me
1971- The Beguiled
1973- High Plains Drifter
1974- Thunderbolt and Lightfoot
1976- The Outlaw Josey Wales
1979- Escape from Alcatraz
1983- Sudden Impact
1985- Pale Rider
1992- Unforgiven
1993- A Perfect World
1993- In the Line of Fire
1995- The Bridges of Madison County
2004- Million Dollar Baby
2008- Gran Torino