Actor, director, mayor, family man and granite-faced defender of truth, justice and the American way, Clint Eastwood’s career has spanned six decades, from the fresh-faced cowboy in TV’s ‘Rawhide’ to the grizzled veteran who scored a box-office smash with one of the biggest films of 2014, ‘American Sniper’. From range-riding westerns to Cold War action movies, from hushed romances to historical dramas, Clint’s directorial CV is a fascinating, unpredictable mixed bag. We watched them all – and listed them in order of greatness.
The silliest movie of a career that includes ‘Space Cowboys’, this lifeless supernatural drama about a reluctant psychic (Matt Damon, because why not?), a French tsunami survivor and two creepy British twins is reverse-engineered from the cheesy finale where all of the stories collide into a Hallmark vision of the afterlife. ‘Hereafter’ joins the ranks of ‘Always’ and ‘The Lovely Bones’ as a movie about heaven that feels like it came straight from hell. David Ehrlich
Entombing one of the most interesting lives in American history, this garbled look at the first Director of the FBI (and even more garbled history lesson about how the agency came into being) can’t decide if it wants to be a by-the-numbers biopic or a ‘Citizen Kane’ for power-hungry bureaucrats. Eastwood’s old-fashioned approach sinks the material, and Leonardo DiCaprio’s gutsy lead performance is smothered under pounds of bad movie makeup. David Ehrlich
Possibly fearing that his lifelong commitment to artistry and empathy might make him look a bit, y’know, soft, every so often Clint has to drop a real jarheaded clunker just to remind the world of his boorish Republican credentials. ‘Heartbreak Ridge’ is the most offensive of these, a no-cliché-unturned story of candy-ass recruits under the cosh of their no-bullshit Sergeant (Clint, natch). Imagine ‘Full Metal Jacket’ without the style, substance, intelligence or insight. Tom Huddleston
This silly 2008 drama is the ultimate in ‘Get off my lawn!’ cinema, and not just because Eastwood’s character, a racist Korean War vet named Walt Kowalski, grabs a shotgun and growls those very words at some wayward youths at one point in the film. A floridly melodramatic ode to vigilantism, the story chronicles the friendship that forms between Kowalski and a Hmong kid who lives next door. ‘Gran Torino’ is most notable for the indelible jolt of hearing Eastwood’s death rattle of a singing voice over the end credits. David Ehrlich
Bizarrely viewed as a masterpiece by several notable critics, this is a misguided, self-reflexive attempt to undermine the iconography of the macho filmmaker. Inspired by John Huston’s exploits in Africa while shooting ‘The African Queen’, the film is shoddily scripted and tediously performed, packed with ‘dark continent’ clichés and the kind of crass machismo it purports to critique. Tom Huddleston
Spoiled rich kid Charlie Sheen soon learns to shoot first, ask questions later when he’s teamed with reprobate veteran Clint from the LAPD’s auto-theft section in a cop movie that’s even more hackneyed and cynical than it sounds. Eastwood is practically somnambulant on both sides of the camera, as tired humour and tediously excessive destruction scream sheer contempt for the audience. Trevor Johnston
Hi-tech junk from the Reagan era, this is Eastwood at his near-worst. Its existence speaks less to his talent behind the camera than his undimmed appeal as a box-office draw (which had already withstood co-starring in two movies with an orangutan). Stealing a Russian superplane affords no chance for the actors to get comfortable, but if you put your brain on autopilot, it kills two hours fine. Joshua Rothkopf
Not exactly a career high, this adaptation of the hit jukebox musical was described in Time Out’s review as being like ‘“Goodfellas” without much in the way of stakes’. Gripping it ain’t, telling the story of the rise and fall of Frankie Valli and the Four Seasons. But not even the group’s mob connections (Christopher Walken is knock-out as gangster Gyp DeCarlo) can save ‘Jersey Boys’ from being snore-inducing. Cath Clarke
This ’30s-set Deep South rite of passage sends innocent teen Kyle Eastwood on the road with his hard-drinkin’ uncle (Eastwood Snr, of course), a journeyman country singer seeking one last shot at the Nashville big-time. It’s an ambling, uneven movie, worth revisiting for Clint’s gruff, complex turn as the guitar man who only shows emotion in his songs. Trevor Johnston
Cardiac arrest sends Eastwood’s experienced FBI profiler into retirement, but he later turns private eye when he learns the donor of his new ticker was offed by a serial slayer. Eastwood’s steady pacing and strong cast (Anjelica Huston, Jeff Daniels) lend this gimmicky, ultimately predictable whodunnit more gravitas than it deserves, but it remains a mere time-passer for all concerned. Trevor Johnston
Perhaps unwisely, Clint dips his toe in the currently popular rape-revenge genre for the fourth instalment in the ‘Dirty Harry’ franchise. Like its ‘two random exciting words’ title, this is a predictable, off-the-shelf vigilante flick, with Harry on the trail of Eastwood’s then-paramour Sondra Locke, who plays a sexual violence victim bent on feminist vengeance. That said, the happy ending is surprisingly right-on. Tom Huddleston
Escaping the ‘Dirty Harry’ rut, Eastwood’s a dumb but dedicated Phoenix cop unaware his assignment transporting trial witness Sondra Locke is a set-up jointly engineered by the mob and his corrupt bosses. The bullet-riddled finale proves surprisingly lifeless, but en route sparkling chemistry between stoic Clint and rather sharper Locke recasts generic action fare into a spiky rom-com vibe. Trevor Johnston
Not one of Eastwood’s finest moments, this fairly enjoyable, hysterical thriller imagines that a professional burglar (Eastwood) accidentally witnesses the US President (Gene Hackman) not only having an affair but also committing murder. Which puts Eastwood’s character in a vulnerable position when the full force of a corrupt president comes tumbling down on him. Silly but fun, this has little pretence to be anything other than a good yarn and an excuse for a whole load of chases. Dave Calhoun
Once upon a time, before he started churning out prestige pictures, Eastwood used to make movies like this wonderfully ridiculous 1975 thriller in which he plays a college professor (who also happens to be a retired assassin and one of the world’s most accomplished mountain-climbers) who’s brought back into the fold to kill someone atop a snowy Swiss peak. It was deservedly trashed upon release, but the kitsch is strong with this one, and it’s impossible to completely dismiss a movie in which Eastwood reports to an albino ex-Nazi named Dragon. David Ehrlich
In many ways a partner film to 'American Sniper', this is Clint's second film in a row to strip away the layers of a modern-day hero and get to the real guy underneath. The subject in ‘Sully’ is drastically different from ‘American Sniper’ – pilot Chesley Sullenberger saved hundreds of lives when he landed an airliner on New York’s Hudson river in 2009, and as far as we know he never shot anyone. And with Tom Hanks in the lead, this is an altogether fuzzier drama. But as an investigation into the personal cost of sudden fame, it's fascinating and thoughtful. Tom Huddleston
Clint’s authority-averse investigative reporter uncovers the truth behind a murder conviction, but the race to save the prisoner from imminent capital punishment makes this the hokiest of ticking-clock thrillers. That said, the film’s immense sympathy for Isaiah Washington, the black man facing racially inflected rough justice, is powerfully expressed as he spends his final hours with his loving family. Trevor Johnston
Clint headed to South Africa to remember a pivotal moment in post-Apartheid South Africa’s history: when Nelson Mandela smartly embraced the 1995 Rugby World Cup Finals as a way of progressing along the path of racial harmony in a still-divided country. Morgan Freeman and Matt Damon do decent jobs as, respectively, Mandela and South African rugby captain Francois Pienaar, and the film is noble and compassionate, if a little stodgy in parts. Dave Calhoun
This sweaty, jazzy, dubiously homoerotic and wholly un-Clint-ish melodrama has slipped into obscurity, and it’s a shame. Based on journalist John Berendt’s account of a murder trial in the upper-class enclave of Savannah, Georgia, it’s a ripely enjoyable slice of Southern Gothic sporting fruity performances from Kevin Spacey and John Cusack. The score, a series of covers of trad legend Johnny Mercer, even features the director’s very own dulcet tones. Tom Huddleston
Age 78 and at the top of his game, Eastwood directed this true-life crime drama starring Angelina Jolie as a single mother in 1920s Los Angeles whose nine-year-old son disappears. Five months later, the famously corrupt LA police force knocks at her door with a boy they insist is her son. When she dares to object, she’s discredited and sent to a psychiatric unit. Muscular and moving. Cath Clarke
This Californian cross-generational romance proved Eastwood’s directorial career was no vanity act, the lean precision of his camerawork attentive to every actorly nuance. The old man/young girl outline sounds icky, but the script gives Kay Lenz’s eponymous hippy chick most of the insights, and William Holden – looking older than his booze-ravaged 55 years – is at his most openly vulnerable. Trevor Johnston
Life on the carny circuit proves a struggle for cowboy sharpshooter Clint when Sondra Locke’s snippy fugitive heiress joins his raggle-taggle Wild West show in this unlikely combination of Altmanesque hang-loose ensemble and old-school screwball comedy. Against the odds it’s a triumph, a touching celebration of the regenerative power of myth-making, and the true hidden gem in the Eastwood canon. Trevor Johnston
By some kind of directing miracle, Eastwood avoided turning the mega-selling novel into a smushy lame weepy. ‘Brief Encounter’-style, this is the story of an Italian woman (Meryl Streep) living in Iowa who embarks on a four-day affair with a National Geographic photographer (Eastwood) while her husband and kids are away. It’s beautifully acted, although Eastwood had to fight his corner against producer Steven Spielberg to have Meryl Streep co-star (Anjelica Huston, Cher and Susan Sarandon were also considered for the part). Cath Clarke
Oldsters head to outer space in a geriatric Armageddon that proved vastly more entertaining than anyone expected. Much of the movie’s success can be credited to the seasoned no-bullshit charm of its leathery cast, including Tommy Lee Jones, Donald Sutherland and James Garner. More easy to overlook: Eastwood was directing a Hawksian sci-fi action film with magnificent confidence and heart. Joshua Rothkopf
The title draws on the Book of Revelations – ‘and I looked and beheld a pale horse, and the name of the rider upon him was Death’ – and there’s an appropriately Biblical austerity to this terse, flint-eyed man-with-no-name Western. Clint plays the Preacher, riding ‘Shane’-like into town and taking on the forces of Big Mining. But there are no heroes here, only poverty, misery and death. Tom Huddleston
A slow-building and unlikely blockbuster (the biggest film of 84-year-old Eastwood’s career), this electrifying PTSD war drama became a political football for its questionable handling of the real-life Chris Kyle. But between a nervy performance by Bradley Cooper and some daring ambiguities on the matter of valour, you have a movie that only Eastwood – no simple conservative – could make. Joshua Rothkopf
Most guys in their mid-seventies are thinking about retirement. Not Clint Eastwood, who set about making not one but two ambitious films about the bloody 1945 battle for the Japanese island of Iwo Jima. ‘Flags of Our Fathers’ is the story of the real-life US marines snapped in the iconic wartime photograph raising a flag on the island (its companion film ‘Letters from Iwo Jima’ is told from the Japanese perspective). Eastwood at his best. Cath Clarke
This was Eastwood’s first job behind the camera on a feature film, and he cast himself as a Californian radio DJ who is stalked by an obsessive fan – a stranger who he meets one night in a bar and with whom he has a one-night-stand, only later realising she’s the same person who obsessively calls his show to request the jazz standard ‘Misty’. It’s a strong debut, a claustrophobic psychological thriller with which Eastwood ratchets up the tension all the way to a tense finale. Dave Calhoun
Even with ‘Unforgiven’ earning Eastwood his greatest critical acclaim to date, moviegoers were still surprised by the director’s follow-up: a quiet tale of an escaped convict (Kevin Costner) and the eight-year-old hostage who warms to his unlikely fatherly affection. On paper, it’s a scenario that simply shouldn’t work, but Eastwood’s sensitivity pulls it off, silencing any doubters of his maturation. Joshua Rothkopf
Sean Penn deservedly won an Oscar for his portrayal of an ex-con investigating the murder of his teenage daughter in Eastwood’s darkest movie since ‘Unforgiven’. Is the killing linked to the childhood abduction of an old friend (Tim Robbins) by a paedophile gang? This is a masterful character study based on Dennis Lehane’s novel and set in a working class district of Boston. Cath Clarke
When white-trash wannabe Hilary Swank wanders into wise old trainer Clint’s backstreet gym, another ‘Rocky’ fairytale looms, yet this modern fable takes us into darker territory – the perilous lure of success, the impassable road to redemption. As a performer Eastwood digs deep, as director he holds his nerve to chastening, memorable effect. Oscars for Best Picture and Best Director followed. Trevor Johnston
The second half of a remarkable two-picture project that includes ‘Flags of Our Fathers’, this tells the story of the battle for the island of Iwo Jima from the Japanese perspective, and almost entirely in the Japanese language. Sober, intelligent and as near-devoid of colour as its companion piece, this is a work of compassion. Doubly remarkable was that Eastwood made these two supremely balanced, inquiring pieces about a foreign war while his own country was heavily engaged abroad in a post-9/11 world. Dave Calhoun
This expansive biopic of jazz pioneer Charlie Parker is uncompromised by hagiography or any sell-out to mainstream tastes. Instead it shows the gulf between musical genius and personal frailties bitterly exacerbated by the circumstances of a mid-century black man, a story told with a simmering undercurrent of anger and sadness. A definitive account, thanks to Forest Whitaker’s raging, careening performance. Trevor Johnston
Look closely at Clint’s second movie – and his first Western as director – and you might spot a pair of gravestones bearing the names Sergio Leone and Don Siegel. ‘High Plains Drifter’ might have been nothing more than a slavish tribute to Eastwood’s erstwhile collaborators – ‘A Fistful of Dirty Dollars’, if you like. But it’s so much more: a Gothic horror story, a ferocious revenge thriller and one of the darkest, eeriest revisionist westerns of all. Tom Huddleston
This muscular and captivating Civil War revenge saga, adapted from a novel by noted white supremacist Forrest Carter, is about a renegade who joins up with a gang of pro-Confederate guerrillas. But cut the dual-pistoled madman some slack – Union soldiers murdered his wife and son in cold blood. In fact, Eastwood’s wandering Western is a pacifist plea written in blood, the film version redirecting Carter’s racist energies towards a story about how wars never truly end with a signature on a treaty. David Ehrlich
Eastwood’s masterpiece sums up an iconic career in Westerns, crucially poking a hole in the violent mythmaking that the star himself perpetuated for so long. Based on a thoughtful script by David Webb Peoples that Eastwood kept hidden for decades until he had aged thoroughly, ‘Unforgiven’ sets up a classic showdown, deepening it with notes of phony bluster, regret and a savagery that’s far from heroic. This film (not ‘The Wild Bunch’) is the genre’s true epitaph. Joshua Rothkopf
Discover Time Out original video