We cover the life and times of Clint Eastwood in our latest podcastaganza, looking at his most iconic roles, and his progression as both actor and director. Please join us in this pre-obituary celebration!

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We’re taking a stroll down Clint’s entire career, but there’re a few items we’ve singled out for special attention.

A Fistful of Dollars

We make passing reference to Rawhide, but we’re really interested in Sergio Leone’s Spaghetti Westerns, these being Eastwood’s first noteworthy feature film roles. In all three films – this, For a Few Dollars More and The Good, the Bad and the Ugly – Clint plays the quintessential mysterious stranger, with his ambiguous morality lending some real shades of grey to a genre not then known for it. They all hold up incredibly well today, and Leone’s masterful framing and pacing make all of these a joy to watch.

Dirty Harry

The other elephant in the room is of course the Dirty Harry series, of which the original is still great, and the rest frequently not so. San Francisco cop Harry Callahan does the dirty jobs no one else will, in the first film taking his no-nonsense, beat up first, read rights later approach to a serial killer in a film that’s still tense, impactful and relevant today, providing a template that’s been used time and time again since. It’s an early outing for Eastwood’s right wing political views, no doubt influenced by the greatly increased levels of crime compared to our relatively safe times. The sequels are a real mixed bag, with Magnum Force holding up much better than I’d anticipated as Harry goes on the trail of a gang of cops taking it upon themselves to be judge, jury and executioner. The Enforcer is unfocused and messy, with a bunch of domestic terrorists on the loose with a very poorly defined agenda in a film that appears largely to have been built around the thought that a shootout in Alcatraz would be cool. It is, just about, but the rest of the film isn’t. Sudden Impact‘s a better film, although it feels very much like a completely separate script that Harry sort of wanders through at various points, as he investigates a rape victim who’s taking revenge and frequently is more of a protagonist than Harry. Last and certainly least is The Dead Pool, with someone murdering their way through a list of names tracked back to Liam Neeson’s schlock horror film director’s game of predicting the death of celebrities and such. Eastwood starts the franchise more or less transposing his persona from the aforementioned Westerns, and while this makes for one of cinema’s most iconic characters in the first film, it’s almost become a self-parody by the end, even with Eastwood capable of much better, nuanced performances that the series resolutely resists. The first two films are still worthy of your time, the remainder can be safely purged from your consideration.

Play Misty for Me

This marks Clint’s first directorial effort, which is really the solitary reason it makes the list. A number of puzzling decisions mar this film, most notably Eastwood playing his disc jockey character as though he were Dirty Harry, and an anti-hero is exactly the wrong choice for this plot. He’s stalked and menaced by a crazy, obsessive female fan, but it’s tough to buy her as a credible threat given that she’s squaring off against, well, one of the least vulnerable characters in cinema. With some scenery-chewing overacting, unfocused storytelling and a wildly incongruous soundtrack, this is only useful in showing how far Eastwood has progressed as a director.


Just to reinforce that Clint’s career isn’t all iconic roles and acclaimed directorial turns, Firefox is taken as a representative sample of his late Seventies through most of the Eighties output which tends strongly towards the forgettable. A cold war outing for Eastwood, playing a combat pilot veteran suffering from PTSD, called in as a desperate throw of the dice to infiltrate a Russian facility and steal a wildly advanced, thought-controlled fighter plane that outclasses anything on NATO’s shelves. Its main disappointment comes from the finale, where there clearly wasn’t the technology available to shoot the action the film required, but the earlier infiltration acts do enough to make this a decent enough watch, something that more often than not applies to all of his output in this timeframe – outright poor films are few and far between, but there’s a lot that ultimately left no footprint on cinema history, and Firefox certainly fits right in to that.


We’re back out in the dying days of the Wild West for Unforgiven, which deservedly earned Clint his first Oscar. He directs a fine cast, including himself as a cleaned-up criminal running a failing farm, trying to raise his family after the death of his beloved wife, but he’s tempted to take one last bounty-hunting payday that has him crossing paths with Gene Hackman’s strident small town sheriff. Tremendous performances all round, with a story that effectively dismantles any glamour that may have been nostalgically hanging around the genre in this tale where all of the morality on display is relative, not absolute. While you can certainly see the influence of Leone in this film, it’s tempered with a certain world-weariness of the dying era that all makes for a film that oozes atmosphere. Easily one of his best.

Million Dollar Baby

More Oscars were doled out to this boxing flick, which in large part plays like a fairly standard sporting underdog story as Eastwood plays the grizzled trainer reluctantly taking on Hilary Swank’s female (naturally) boxer, growing rather more fond of her as she improves and finds success. The twist comes from Swank’s sudden disability following a bout, breaking her neck and leaving her paralysed. She has no wish to live out her life in this state, as the film takes a sharp yet seamlessly handled pivot into the drama caused by a euthanasia conundrum. Without that turn this would be an enjoyable movie, but with it we’re left with something rather more affecting. There’re a few moments and characters that wind up on slightly the wrong side of cartoonish, but that’s nothing like enough to blemish another brilliantly directed and acted film.

American Sniper

At the time of recording, American Sniper is Eastwood’s most recent film and one that’s attracted no small share of controversy. Covering deadly U.S. Navy Seal sniper Chris Kyle’s tours of Iraq, along with some small looks at his domestic life, this would seem to be a great opportunity to look at the effect of war and in particular the unique role of snipers in asymmetric modern combat, but the film takes great pains to seemingly avoid any sort of introspection or examination at all. Without that it’s tough to take it as anything other than a biopic that plays fast and loose with the details of his life in search of a narrative that doesn’t really emerge. While it’s a useful base to project your politics on to for the purposes of any number of debates, as a film we can’t help but feel it’s a surprisingly uncontentious missed opportunity.

A bit of a downer to end with, but there’s no mistaking Clint’s contribution to cinema both behind and in front of the camera that made this a pleasure to record. We hope it’s half as enjoyable to listen to.

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