2. Unforgiven (1992)
Tomatometer: 96 percent

Seven years after revisiting the Western with Pale Rider, Eastwood made one final return to the genre -- and what a return it was. Even by its director and star's inflated career standards, Unforgiven was a smashing success, going on to win Academy Awards for Best Picture, Best Director, Best Editing, and Best Supporting Actor -- and, ultimately, to enshrinement in the United States National Film Registry. Viewed in the context of Eastwood's unsentimental Westerns, Unforgiven represents the ultimate deconstruction of the genre's myths, presenting Eastwood as an aging gunslinger whose soul has been irrevocably stained by the violence of his past. It contains some of his best work as both a director and an actor, and is, in the words of Time Magazine's Richard Corliss, "Eastwood's meditation on age, repute, courage, heroism -- on all those burdens he has been carrying with such good grace for decades."

1. The Outlaw Josey Wales (1976)
Tomatometer: 97 percent

Even for a guy who'd already demonstrated a fondness for revisionist Westerns, The Outlaw Josey Wales is a special case, arriving at the box office during a time when most people had written off the entire genre for dead -- and presenting its hero as the innocent victim of marauding Union soldiers during the Civil War, to boot. (Josey Wales was adapted from a novel by Forrest Carter, a name later revealed as a psuedonym for former Klansman and George Wallace speechwriter Asa Carter, but its themes of racial inclusion don't reflect Carter's stated beliefs.) Packed with action and humor, the movie continued Eastwood's winning Western streak, and further cemented his reputation as a talented director -- a role he assumed on this project from the original helmer, Philip Kaufman, prompting the DGA to insert the so-called "Eastwood rule" into its contract, stating no cast member could take over for a departing director. Whatever behind-the-scenes drama it caused, Josey is, as the Tyler Morning Telegraph's Jonathan R. Perry said, "Eastwood's brooding, bloody masterpiece."