"Blood Work" (2002)
This, for this writer at least, was the first indication that maybe Eastwood shouldn't direct every good script that slides across his desk. "Blood Work" was adapted from a crackerjack Michael Connelly novel by the great Brian Helgeland (who would become a frequent Eastwood collaborator) and is centered around a hum-dinger of a crime movie conceit. Eastwood plays a FBI Agent whose life is saved by a heart transplant. The person whose heart Eastwood received was murdered, and the murder victim's sister (played by solid character actress Wanda de Jesus) implores Eastwood to solve the crime. It's a thriller with all of these built-in psychological and spiritual questions, plus a really cool plot. What could go wrong? Well, Eastwood's sluggish direction, for one; plus the fact that Eastwood is just not a great director of suspense set pieces (some may disagree, but the thriller aspects of "Mystic River" were probably its soggiest; ditto “Absolute Power”). Taking your time and building things appropriately makes sense, but when you could feel that the audience was a few steps ahead of the director (and the characters on screen), something was wrong. It was one of the first times that you felt Eastwood's age as a director, and it felt OLD. [C+]

"Mystic River" (2003)
For film auds coming of age in the shadow of Dirty Harry, “Mystic River” marked the resurgence of Clint Eastwood, Oscar-winning director of note. For most everyone else, this was a strong-willed reminder that Eastwood continues to be a considerable talent behind the camera. Based on the novel by Dennis Lehane (who’s built an empire of evoking gritty morality tales of working-class Bostonians caught between forever blurring lines of right and wrong) and adapted quite capably by screenwriter Brian Helgeland, “River” brought together three reliable actors - the powerhouse (Sean Penn, who went FTW with Oscar, ousting Bill Murray’s well-deserved nom for “Lost In Translation” in the process), the ambitious character actor and occasional leading man (Tim Robbins, pocketing an Oscar as well) and the 6-degrees-of-separation-inspiring nervy everyman (Kevin Bacon, suspiciously and acceptably toned down). Their intertwined stories, along with a murder investigation led by Bacon and the occasionally slumming Laurence Fishburne, form the crux of a expansive Boston-set boiler that is rooted in the very basic Eastwood theme of vengeance. “Mystic River” is likely to be remembered for Penn and Robbins, who turn in career-defining work, Penn as a grieving father with a criminal past who isn’t afraid to bloody his hands and Robbins as a wrecked man-child forever haunted by a vicious act of abuse. Marcia Gay Harden and Laura Linney, relegated to “wife” territory, deliver terrific performances and guided by Eastwood’s sure hand, the cast and the film involves and occasionally captivates. The multiple plot-lines don’t cohere with the kind of dramatic tension Eastwood might be shooting for but the ending is appropriately chilling and ties the personalities on display here with a grand tear-jerker of wrongly dealt out punishment - not a great film, but a memorable warm-up for the renewed vigor of the Clint Eastwood of the aughts. [B+]

"Million Dollar Baby" (2004)
It will be difficult to qualify just how much acclaim rewarded to this 2004 Best Picture had to do with tackling a largely unspeakable subject in a sensitive and intelligent way. To reveal the twist (literal and figurative - bad taste, I know) is to bare the heart of the film, which this writer never found to be particularly moving. “Million Dollar Baby” is hardly a departure for Eastwood, the same themes and Catholic guilt resting on the shoulders of Frankie Dunn (Eastwood) - Dirty Harry as boxing gym owner and former manager. Enter Maggie Fitzgerald - Brandon Teena meets Rocky played with grift and no shortage of stubbornness by Hilary Swank, scoring her second Oscar in five years. Yes, Frankie takes on the challenge of Maggie. Yes, he molds her into a fighter to be reckoned with. And yes, Morgan Freeman’s aging pugilist and Frankie’s conscience, watches over the Eastwood and Swank as they slowly rise to the occasion, facing the present while dealing with the sins of the past. Freeman is probably the best thing about the film, warm and all-knowing, and seemingly ever-present. Hmmm... To be frank, revealing the trajectory of Maggie as a human being first and a boxer second would undermine the very element of surprise the film attains on first viewing. So as an admirer, rather than an unabashed fan, this writer would like to say this is a solid film that sticks out in the boxing genre as something unabashedly more earnest, coupled with top-notch performances and painted in somber, funereal tones. [B]

"Flags Of Our Fathers" (2007) & "Letters To Iwo Jiwa" (2007)
Easily Clint Eastwood’s most ambitious undertaking of his entire career, the one-two punch of the “Flags Of Our Fathers” and “Letters From Iwo Jima” was supposed to be the grand scale tale of one of World War II’s bloodiest battles from both sides of the trenches. Unfortunately, both pictures were plagued by the same problems: gooey sentimentality, clichéd characters and a sloppy structure underselling whatever impact each film individually or collectively could have had. "FOOF" found Eastwood confronting a number of thematic elements but never quite delivering on the promise of them. Instead the film seems to run out of Eastwood’s grasp and the last third is overloaded with a voice narration that is hardly used in the rest of the film. Simiarly, "LFIJ," finds itself with the crutch of a flashback heavy narrative and a teary tone that is hammered home instead of earned. Eastwood’s films are almost painfully polite, lacking teeth and direction. The same American soldiers that Eastwood takes pains to humanize in "FOOF" are turned into savages in "LFIJ," and the reverse is true as well. By the end of it all, Eastwood has made two films that are somber, mature and utterly empty without anything original to say. There is a great single movie somewhere in here that would allow for an interesting perspective on the soldiers, the battle and what was going on both fronts but Eastwood failed to find it in two movies.
"Flags Of Our Fathers" [C]
"Letters From Iwo Jima" [C-]