Note that this list isn't comprised of the five best Eastwood films. Rather, it's just one fan's personal faves. And since this is a classic movie blog, I've focused on Clint's work through the 1980s.
1. The Outlaw Josey Wales (1976). Eastwood's fifth film as a director spotlights two of his favorite themes: the bonding among outcasts and personal redemption. Set after the Civil War, Eastwood portrays the title fugitive, a former farmer who rediscovers his humanity as an assortment of outcasts join him on his quest for revenge. Eastwood skilfully blends action, comedy, and character development. I think this one also ranks near the top of any list of his best movies.
2. The Gauntlet (1977). Because Clint plays a tough police detective in The Gauntlet, it often gets lumped in with the Dirty Harry movies. It's a very different picture, with Clint playing Ben Shockley, an alcoholic, none-too-bright detective assigned to protect a witness (Sondra Locke) testifying against the Mob. When she makes Shockley realize he's being used, he finally digs down inside to find the man he could have been...or, perhaps, still could be. The Gauntlet is fast and funny (especially when the two leads are sparring) and the ending is delightfully over the top.
3. Two Mules for Sister Sara (1970). It's hard to imagine a more unlikely duo than Clint Eastwood and Shirley MacLaine. Perhaps, that's what makes them such a perfect pair in this lighthearted Don Siegel Western. Clint portrays a soldier of fortune who rescues a nun from bandits and helps Mexican revolutionaries fight against the French. Things get complicated when the grizzled cowboy finds himself attracted to the whiskey-drinking, cigar-smoking Sister Sara. Budd Boetticher wrote the original story and intended it as a vehicle reuniting Heaven Knows, Mr. Allison co-stars Robert Mitchum and Deborah Kerr.
|Clint with Sondra Locke.|
5. For a Few Dollars More (1965). My favorite of the Clint Eastwood-Sergio Leone collaborations pairs Clint with fellow bounty hunter Lee Van Cleef. They are both pursuing the notorious outlaw El Indio--though for very different reasons. Clint wants the bounty, while Van Cleef's reason isn't revealed until the climax (a trick used by Leone even more effectively in the later Once Upon a Time in the West). The success of this Spaghetti Western has as much to do with Van Cleef as Clint, but the two make a great pair.
Honorable Mentions: Where Eagles Dare is a near-perfect action film, but Clint isn't really the star; Kelly's Heroes; and Magnum Force (Dirty Harry may be a better movie, but Magnum is more fun).