20. “Sudden Impact” (1983)
In light of “Dirty Harry” being his signature franchise and arguably his most iconic role, it’s not surprising that Eastwood eventually ended up directing one of the selfsame movies. It’s just a little disappointing that even Eastwood couldn’t make a sequel as effective as Don Siegel’s original. “Sudden Impact,” the fourth in the series (it’s also the introduces the character’s best line, “Go ahead, make my day”), is a slightly uneasy blend of the usual near-fascistic cop procedural and a “Death Wish”-style rape revenge movie, as Eastwood’s Harry Callahan is tasked with investigating a series of vigilante killings by the survivor of a gang-rape (Sondra Locke, Eastwood’s partner and regular co-star at the time). The film was originally conceived as a solo vehicle for Locke before it was turned into a ‘Harry’ picture, and it shows: it’s over-stuffed, sloppily plotted, and more than any other film in the franchise feels like a TV episode. But Eastwood has the intrinsic understanding of the character’s base appeal that you’d expect him to have, and as such there are a number of cracking sequences here and a payoff that ultimately feels satisfying.
19. “Absolute Power” (1997)
Based on one of the most successful airport novels of the post-Grisham 1990s, “Absolute Power” has an all-time ludicrous logline: in the course of a break-in, a successful jewel thief (Eastwood) accidentally witnesses a drunken tussle between a man and his mistress, which ends in the man’s bodyguards shooting and killing the woman. The powerful man being, of course, the President of the United States (Gene Hackman). Despite its best intentions, the film never quite overcomes the ridiculousness of its central plot. The cast, save a somewhat-on-autopilot Eastwood, are strong, with hall-of-fame character actors like Laura Linney, Ed Harris, Scott Glenn, Judy Davis, Melora Hardin, Richard Jenkins and even E.G. Marshall (in his final screen role) turning up, and there are a handful of decent setpieces. But even William Goldman, who wrote in his must-read memoir “Which Lie Did I Tell” that the script was the hardest job of his career, can’t make the plot work, and it doesn’t help that Eastwood’s typically languid pacing doesn’t suit this kind of “24“-style potboiler. You might not mind if it turns up past midnight on TV, and it’s still better than either “True Crime” or “Blood Work” in the “mediocre Eastwood crime pic” trilogy, but it’s a very, very minor effort all the same.
18. “Letters From Iwo Jiwa” (2007)
Made for less than a quarter of the budget, yet faring marginally better at the box office, the companion piece to “Flags of our Fathers” suffers from many of the same flaws, but has at least a fresher point of view. Still a somber, mature and very respectful film (Eastwood is perhaps even more involved in humanizing and sentimentalizing the Japanese soldiers’ journeys than he was with the Americans in the prior film), ‘Iwo Jima’ simply works better because the story it tells requires and rewards an effort of empathy on behalf of both filmmaker and audience that is somewhat baked-in with ‘Flags.’ The flashback-heavy narrative and rather on-the-nose storytelling can’t overpower the simply humanity of exploring a famously bloody and costly battle through the eyes of the enemy, and cannot conceal the clear, sad fellow-feeling with which Eastwood (and writer Iris Yamashita, with Paul Haggis getting a story credit) regards the Japanese soldiers on the ground. Had Eastwood been forced to make ‘Flags’ and ‘Iwo Jima’ as one film, one can only imagine how much richer and more impactful an experience it might have been. As it is, ‘Iwo Jima’ feels like half a film. But at least it’s the better half.
17. “White Hunter Black Heart” (1990)
Considering that he’s now spent over 60 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 to 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“) will be disappointed. This doesn’t strike one as anything close to Eastwood’s on-set style, even if you substitute “trying to shoot an elephant” for “playing a round of golf.” It is an undeniably enjoyable film: it’s somewhat looser and funnier than much of Eastwood’s work, and its examination of machismo shows the director to be a more contemplative figure than his onscreen persona sometimes suggests. But Eastwood the actor seems out of his depth, seemingly 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 an entertaining one man show only really let down by that one man.
16. “Midnight In The Garden Of Good and Evil” (1997)
Eastwood took on his third best-seller in a row with “Midnight In The Garden Of Good and Evil,” but true to form, it saw a major left turn for the filmmaker, abandoning the housewives romance and the airport thriller for a full-on slice of Southern Gothic. Based on John Berendt‘s true crime book following the four trials of Savannah antiques dealer Jim Williams for the murder of his rent-boy lover, the adaptation (which sees Eastwood reunited with “A Perfect World” writer John Lee Hancock) condenses the trials down to one and adds a reporter character played by John Cusack who is our eyes into the bizarre Georgia of the book. Kevin Spacey, as Williams, gives a terrific performance, and Jude Law makes a strong impression in a relatively early role. But Cusack’s given next to nothing to do, and the casting of Eastwood’s daughter Alison feels nepotistic at best. Frustratingly, there are glimpses of the kind of perverse mood piece this could have been had the book’s heady sense of place been better established, but even the real-life residents of Savannah like drag queen Lady Chablis never come across as anything more than window dressing.
15. “Space Cowboys” (2000)
“Old coots in space” seems like a logline cooked up by a bored executive on a lazy afternoon. But in Eastwood’s capable hands, it turns into something quite entertaining and peppered with moments of pure popcorn excitement despite its marathon 130 minutes. The old coots (played by Eastwood, Donald Sutherland, James Garner and Tommy Lee Jones, with an assist from James Cromwell) have to go into space to repair an ailing satellite that is so out of date that they’re the only ones with the knowledge to fix it. So the concept is somewhat sound, but the real fun of the film is watching the fogies get back into NASA-approved shape, with each actor exaggerating their ornery old timer-ness to an almost cartoonish degree. Once the mission gets underway, Eastwood handles the action beats (which border on sci-fi, a genre he’s never had much use for) with flair, thanks in large part to the heroic visual effects by Industrial Light & Magic. Sadly, as the film reaches its conclusion, “fun” is swapped out for “achy melodrama,” and the energy sustained for so long slips away. Till then, it’s good old-fashioned fun for a rainy Sunday with your in-laws.
14. “The Gauntlet” (1977)
A movie that has its fans (it has been reissued on Blu-ray, so people obviously still dig it) and is entertaining in a down-and-dirty, genre-picture-made-in-1977 type of way, “The Gauntlet” is still in no way as memorable as its macho-overload poster, designed by the one and only Frank Frazetta. That image is an oversized depiction of the movie’s extended finale, in which an alcoholic Ben Shockley (Eastwood) escorts a loudmouth prostitute (Sondra Locke), who also happens to be a witness in a huge corruption case, through the titular gauntlet of corrupt cops. But the poster also suggests an almost “Mad Max“-esque level of post-apocalyptic devastation, which teases a much more interesting and vibrant movie than Eastwood actually delivers. While the plot moves quickly along and he stages the action sequences with the appropriate flair, “The Gauntlet” is a little hamstrung by the decision to cast Locke (whom Eastwood was dating at the time), and by the kind of terminal forgettability that seems to have blighted quite a few of the director’s less robust earlier outings. Or maybe it’s just that for muscularity and hilarious, borderline-parody hijinx, it simply can’t hold a candle to that poster.
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13. “American Sniper” (2014)
It’s difficult to discuss Eastwood’s biggest hit by a huge distance without talking about its enormous box-office success in North America, seemingly powered by every Red State voter who ever lived. A patriotic/jingoistic picture about PTSD, American sacrifice and the horrors of war, “American Sniper” was meant to have been a stirring, complex account of these elements seen through the lens of one of America’s all-time greatest sharp shooters, a very troubled man who couldn’t comfortably exist outside the dysfunction of war, which had become his normalized way of life. But Eastwood, notorious for shooting two takes or fewer, directs the movie like he can’t wait to break for lunch; nothing breathes, the good performances never quite get the chance to be great and none of the emotion of the piece really lands (Steven Spielberg nearly shot this movie and one can only imagine how much more powerful his version would have been). Fittingly, “American Sniper” is a mess of a movie when it’s at home —#fakebaby, #neverforget— but works with cold, clean precision when sequestered in Iraq. In fact, it’s the movie’s taut and terrifically crafted action sequences, like the harrowing desert storm action scene, that almost save it.
12. “The Bridges Of Madison County” (1995)
Surely the chick-flickiest entry in Eastwood’s directorial canon, ‘Madison County’ is essentially a “Brief Encounter” retread: a story of decent, honorable people struggling with dishonorable urges but ultimately choosing the not terribly fulfilling rewards of Doing the Right Thing over Following Your Passion. Based on the literary phenomenon that was the novel of the same name (though ‘novel’ is a misleading word, as the average National Enquirer probably takes longer to read), the film, aside from some wooden supporting performances (particularly from the grown up children who Learn A Little Something About Life from reading their mother’s journals), has actually weathered the passage of time rather well, mainly because at its heart is the utterly convincing relationship between Eastwood’s photojournalist and Meryl Streep’s Italian-born Iowa housewife. The film is really a two-hander, with everything outside of the two leads talking themselves into and out of their love affair feeling totally extraneous. Streep, especially, is sublime: in her hands, small nuances, like covering her mouth when she laughs, suggest whole interior worlds of unrealized dreams and thwarted desires. It’s to Eastwood’s credit as a director and a co-star that he recognizes when he’s on to a good thing and graciously stays the hell out of the way.
11. “Honkytonk Man” (1982)
Oftentimes, even in Eastwood films that aren’t westerns, the idea of the lone cowboy character embarking on a quixotic mission while the world seems to be moving on without him is central. And so it is with this unusually low key and largely overlooked road movie, in which Eastwood plays shiftless drunken country singer Red Stovall (reportedly loosely based on Jimmie Rodgers, the first artist who can be said to have truly played country music) who is on a Hail Mary odyssey to get to the Grand Old Opry in Nashville before his advanced tuberculosis kills him. Accompanying him on the journey (because every cowboy needs a sidekick) is his nephew, played by Kyle Eastwood, and his horse on this occasion is a car, a beautiful vintage Lincoln model K that dies, like the loyal beast it is, by Red’s grave. It is slow and episodic, but there is a pensive wisdom to the film, and despite its anticlimactic trajectory, there’s a gentle uplift that sets it above many of Eastwood’s more gung-ho titles. The pair visit brothels and gambling parlors and pick up dippy companions along the way, but this is really about a man’s journey to his dream.