27. “J. Edgar” (2011)
Eastwood has many admirable qualities as a director, but one unenviable trait is the propensity for taking real-life stories that are full of intrigue and texture and turning them into terminally tasteful stodge. “J. Edgar,” his biopic of the despotic, notoriously hypocritical head of the FBI throughout its formative decades in the mid 20th century, laudably paints Hoover (a committed Leonardo diCaprio) as neither saint nor monster, but instead just makes him seem pretty dull. Scripted by “Milk” screenwriter Dustin Lance Black, the film doesn’t shy away from Hoover’s sexuality, but is stymied by Eastwood’s fastidious aversion to the erotic (Eastwood’s sex scenes are almost always rote), delivering little more intimate than a kiss, some hand-holding and an impromptu wrestling match. This might not be a problem, except that by its sentimentalized close, the film becomes more or less a love story between Hoover and his companion Clyde Tolson (a very good Armie Hammer, who gets lumbered with the worst of the film’s very poor old-age effects). Aside from missing out on some of the more dramatic possibilities offered up by such a storied life, “J. Edgar” becomes hard to swallow when it suggests that Hoover’s dubious legacy was somehow ennobled by a lifelong love he only ever lied about.
26. “Changeling” (2008)
Made with consummate care and craft, yet still surely standing as the most dispiriting film in Eastwood’s catalogue, this vehicle for Angelina Jolie mines its heartbreaking story so earnestly that it strays dangerously close to emotional torture porn. In case you don’t know, or spent the day doing something more uplifting like having your dog put down, the based-in-truth plot revolves around a single mother who does not believe the boy claiming to be her lost son is in fact her missing child. Pitted against the authorities who just want the case closed, she is committed to an insane asylum before eventually being vindicated, if that’s the right word, by the discovery of the actual hideous fate of her real son. Eastwood’s not really one for subtext, and with the main storyline here being one of such choking injustice, cruelty and horror, there is no shading here, no scrap of redemption, catharsis or even any real retrospective wisdom to be had. So “Changeling,” which landed Jolie, the art directors (James Murakami and Gary Fettis) and the cinematographer (Tom Stern) Oscar nominations, ultimately ends up little more than an almost fetishistically cataloged litany of this poor woman’s ordeals. And for what?
25. “Jersey Boys” (2014)
Basically every filmmaker wants to make a musical at some point, and when his planned remake of “A Star Is Born” collapsed, Eastwood switched streams and took on this long-gestating adaptation of the Broadway tourist-bus favorite (which was originally to have been directed by Jon Favreau before the film got put into turnaround). Telling the story of Frankie Valli And The Four Seasons over four decades as they go from petty criminal activities to rock and roll legends, it sometimes feels more like a Behind The Music episode than an actual movie, hitting every beat and life event in the way you might expect, but never really letting you get to know the subjects on anything more than a surface level. And while Eastwood’s insistence on hiring mostly original stars of the stage show to headline the movie, it leaves something of a charisma vacuum on screen, with the film only really coming alive when Christopher Walken pops up as mobster Gyp DeCarlo. Diehard fans of Valli and co. who never made it to a touring production of the show might have a good time, but it’s hard to know otherwise who this is for, or why a director who could make a film as impassioned about music as “Bird” would choose to shoot it.
24. “Heartbreak Ridge” (1986)
In some ways, “Heartbreak Ridge” might be the Platonic ideal of what many think of as an Eastwood picture: it’s a right-leaning, red meat, no nonsense drama celebrating masculinity and America. That it’s so familiar is likely why the film isn’t often held up among his best efforts —it does its job fairly adequately, but it’s such a low-stakes film that it’s hard to get worked up about it. Though the title refers to a battle in the Korean War, this military drama is actually set in the early 1980s, as hard-ass Marine Corps Sergeant Thomas Highway (Eastwood) is put in charge of a rowdy, ragtag bunch of recruits and has to knock them into shape before they can invade Grenada. The film is one of the earliest signs of a certain “will-this-do? let’s-just-wrap-this” sensibility that has often marred Eastwood’s career: the story is so by the numbers and the filmmaking often feels merely functional. But it’s actually encompasses one of his best performances as an actor: as familiar as his character is, Eastwood finds both an atypical lightness that makes the film go down easy and a melancholy that looks ahead to the more elegiac work that would come in the 1990s.
23. “Flags Of Our Fathers” (2007)
Perhaps the most extreme and ambitious example of Eastwood’s fondness for telling his stories in the most straightforward manner possible, even when they are complex, multi-stranded and multifaceted true stories, came in 2007 with his double album “Flags Of Our Fathers” and “Letters To Iwo Jiwa.” The first to arrive and perhaps the more typically Eastwoodian, though also the lesser, is ‘Flags,’ a narrative about the WWII Battle of Iwo Jima told from the point of view of American combatants. It finds Eastwood confronting a number of thematic elements —survivor’s guilt, the manufacture of heroism, the hollowness of the idea of glory in battle— but never quite exploring them to their fullest extent. It follows three young soldiers (Ryan Philippe, Jesse Bradford and Adam Beach) who are doomed to become symbols, repeatedly recreating the battle’s most famous image —the raising of the American flag over the battlefield— and even being immortalized in the famous statue. But while the film exposes that hypocrisy, it never delves any deeper than a standard ‘war is hell’ narrative. In fact at times, it delivers its story with an excess of sentimentality and a teary tone that never feels entirely earned, particularly in the unsatisfying, voiceover-heavy last third.
22. “Blood Work” (2002)
Maybe Eastwood shouldn’t direct every high-concept script that slides across his desk: “Blood Work” was adapted from a crackerjack Michael Connelly novel by Brian Helgeland (who would become a frequent Eastwood collaborator) and is centered around a humdinger of a crime movie conceit. Eastwood plays an FBI Agent whose life is saved by a heart transplant. The person whose heart Eastwood received was murdered, and the victim’s sister (played by Wanda de Jesus) implores Eastwood to solve the crime. It’s a thriller with many 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 can feel that the audience is a few steps ahead of the director (and the characters on screen), something is wrong. It’s one of the first films in which you feel Eastwood’s age as a director.
21. “True Crime” (1999)
Less farfetched and silly than some of Eastwood’s other late ’90s/early ’00s procedural thrillers, “True Crime” is also rather more familiar: the story of a crusading journalist (Eastwood)’s attempt to free a Death Row inmate (Isaiah Washington) in the hours before his execution is a very old one, and at times the film creeps close to self-parody (Eastwood presumably didn’t see “The Player,” for one). And he approaches the subject with a puzzling lack of urgency —the clock doesn’t so much tick as plod, and even as the end approaches, there isn’t all that much in the way of suspense (perhaps a tacit acknowledgement that you know how it’s going to play out anyway). But what “True Crime” lacks in suspense, it makes up for with a degree of humanity and texture. Eastwood’s journo has some fun scenes with his superiors (Denis Leary and James Woods), there’s a fine lineup of character actors scattered throughout, and Washington in particular is superb, reminding us of the promise he held before his homophobic self-destruction on “Grey’s Anatomy.” “True Crime” is decidedly minor even by Eastwood’s prolific standards, but has plenty to recommend it.
