"Bird" (1988)
Considering his reputation as a big-screen tough man, it's somewhat remarkable that one of the more successful and sensitive musical biopics, a genre full of disastrous attempts to overexplain legends, came from Clint Eastwood. But the noted jazz enthusiast (his son Kyle is a jazz musician, and Eastwood Sr. composed jazz-inflected scores for several of his films of the '00s, as well as for James C. Strouse's "Grace Is Gone") hit a real passion project with Charlie Parker biopic "Bird" and his love for the music and the man shines through. Forest Whitaker, in one of his earliest high-profile roles, is sensationally good, picking up a Best Actor award at Cannes, with the ever-underrated Diane Venora easily his match as his last wife Chan. It doesn't shy away from the darker aspects of Parker's life either (he was addicted to heroin for basically all his adult life), but still manages to keep on the right side of cliche. However, the film falls down in its loose structuring, which is appropriately jazz-like, but rather works against the picture, and it's hard to walk away without feeling that 20 minutes could have been happily shaved from the film. What shines through, however, is Eastwood's love of the music, which is outstanding -- Eastwood and music coordinator Lennie Niehaus isolated Parker tracks from original recordings, then mixed them with contemporary musicians, paying tribute to the man while keeping the music fresh. [B+]

"White Hunter Black Heart" (1990)
Considering he's now spent over 50 years on film sets, you'd think that Eastwood would have made movie-making the subject of a film earlier than 1990's "White Hunter Black Heart." But anyone looking at this film for an insight into Eastwood's working methods -- his portrayal of obsessive director John Wilson (a very, very thinly veiled version of John Huston during the making of "The African Queen") doesn't strike one as anything close to Eastwood as director, even if you substitute "trying to shoot an elephant" for "playing a round of golf." It is an undeniably enjoyable film -- somewhat looser and funnier than much of Eastwood's work -- and its examination of machismo shows the director to once more be a more contemplative figure than his onscreen figure sometimes suggests. But Eastwood the actor seems out of his depth, seeming preoccupied with impersonating Huston, and coming across as somewhat mannered as a result. Jeff Fahey is fairly strong as his foil, and George Dzunda is entertaining as the Sam Spiegel surrogate, but for the most part this is a one man show where the one man proves to be a disappointment. [C+]

"Unforgiven" (1992)
Considering it's now close to twenty years since he tackled the genre, one would think that Eastwood would have considered returning to the Western by now -- after all, Kevin Costner doesn't seem to be able to go five years without taking another crack at the genre. But then, if we'd made "Unforgiven," we're not sure we'd have anything left to say either. Almost inarguably the crowning achievement of Eastwood's career to date, the revisionist Western had been floating around the industry for years, with the director eventually buying up the rights, but deciding to wait until he was old enough to pull off the lead role. And we're glad he did -- no-one else would have brought the baggage (and we really do mean this in a good way) that Eastwood does here; the history of his career weighs heavy on the shoulders of Bill Munny. The key line here is "It's a hell of a thing, killing a man. Take away all he's got and all he's ever gonna have," and Eastwood plays Munny as though the weight of every life he took on screen, from The Man With No Name to Dirty Harry, is catching up with him. He's ably assisted by a killer supporting cast, particularly Gene Hackman, Morgan Freeman and Richard Harris, and a magnificent script from David Webb Peoples ("Blade Runner"). Eastwood's never felt so confident behind the camera, either, and his take on the genre that he'd already made a hell of a stamp on has influenced everything since, from HBO's "Deadwood" to the Coen's upcoming "True Grit." He's not topped it since, but we'll put up with "Changeling" or "Hereafter" if we think that Eastwood will ever get close to this again. [A+]

"A Perfect World" (1993)
Coming off probably the greatest achievement of his acting and directing career (and an acting-only role in the sizable commercial hit "In The Line of Fire" in between), nobody expected Eastwood to match "Unforgiven" next time out at bat. What was truly surprising was how close the director came with "A Perfect World." Teaming for the first and only time with Kevin Costner (at that time, and it's hard to conceive now, easily the biggest movie star in the world), Eastwood originally intended to only direct, but was persuaded by Costner to take on the supporting role of Texas Ranger Red Garnett, who pursues escaped convict Butch Haynes (Costner) after he takes an eight-year-old Jehovah's Witness boy hostage. Eastwood's solid, but it's the performances he draws from both Costner, who's rarely been better, proving enormously sympathetic without ever letting us forget the cold-blooded killer that he is, and child actor TJ Lowther, that make the film. Maybe, at close to two-and-a-half hours it's a touch too long, but as Eastwood's most lyrical film (you wouldn't be crazy to call it Malick-esque in places), you'd be reluctant to cut a frame. And the deep, desperate melancholy, and unexpected humor, mean that, while it may never quite get the due it's owed, it'll remain the great hidden gem of Eastwood's directorial career. [A+]