The Evolution of Eastwood: The First Twenty Films

Ever since “the man with no name” rode through Sergio Leone’s haunted western territory, Eastwood seemed destined for greatness. His early filmography is populated mostly by westerns and cop thrillers (including perhaps his most signature role as “Dirty” Harry Callahan), with a few odd exceptions that would hint at some truly interesting things to come.

Having made this chronological journey through the first third of his filmography, I wanted to take a brief beat to examine some of the trends that emerged and identify some elements that defined the early period of his film career. There are absolutely elements deserving of praise, but also some disappointing trends as well. So, speaking in broad terms, here’s what I learned watching the first twenty films in “The Evolution of Eastwood”…

The Embodiment of Tough

One of the most common elements in each of Eastwood’s first twenty films is that he’s one intimidating s.o.b. His trademark squint (which first emerged as an accident due to lighting on the set of A Fistful of Dollars) would come to represent that steely, cold iron that apparently serves as a spine to each of his characters. In every single film, Eastwood’s character never loses a one-on-one fist fight (or gunfight for that matter) and the few times that he is subdued, it’s because of a multi-man ambush (for which he always doles out revenge). There are only two times in this early track in which Eastwood plays a remotely vulnerable character against whom the odds are sufficiently stacked. And, ironically, in both cases his opponents are women.

Misogyny Overload

I’ll not mince words here – in both his films (and apparently his personal life) – Eastwood doesn’t have a very upstanding reputation with women. His personal life is littered with numerous rumors of affairs (and an undetermined amount of children) and some of the authenticated details of his longer-term relationships don’t paint him in the best light. That sensibility makes its way into most of his on-screen personas as well, as he frequently seduces or coerces women into lovemaking only to treat them with rather questionable dignity afterwards. In High Plains Drifter, he outright rapes a woman in the first fifteen minutes of the film (a narrative element that is in direct alignment with the tone and theme of the film, but is disturbing nonetheless). It is interesting to me, then, that two of his stronger and more compelling films (Play Misty for Me and The Beguiled) feature him playing a character at the mercy of powerful (but unfortunately crazy) women. Both of those films represent strong pieces of filmmaking and strong performances from Eastwood, but it does little to dilute the already misogynistic trends in his early filmography.

Two major exceptions here is Shirley Maclaine’s turn in Two Mules for Sister Sara, which features a strong and resourceful woman, and Kay Lenz’s portrayal in Breezy (which Eastwood actually directed without starring in it). However, in both films, despite the maturity and actualization of the Maclaine’s and Lenz’s characters, they still fall for men who are of at least moderately questionable character – and who still exhibit disappointing attitudes towards women. These criticisms could be hurled as much at the sensibilities of the era in which Eastwood rose to fame as they could at Eastwood himself (more-so probably), but when taken in large chunks of viewing like this, the trends are hard to ignore or excuse.

A Question of Ethics

One of the most compelling and fascinating elements of Eastwood’s filmography is the consistent exploration of questionable ethics and morals. From his very first feature film (A Fistful of Dollars) through his dramas and thrillers, he is constantly exploring characters with foggy boundaries dividing right from wrong.

Take, as a brief example, his signature character of Dirty Harry. Harry Callahan is often a cold-blooded vigilante, frequently breaking the law to uphold it, who stubbornly denies the rights of criminals to protect the rights of victims. The dark complexity of the violence in those films caused several other A-listers to give it a hard pass, but it fit in perfectly with Eastwood’s revisionist persona of icons. His western heroes have sensitivity towards common everyman, but they are ruthless and cold-hearted towards the villains. This is never more deeply embodied than in his disturbing but powerful film High Plains Drifter, in which the very notion of justice as served by a devil is explored. Even in his lesser known mission/war films such as Kelly’s Heroes, Where Eagles Dare, or The Eiger Sanction, Eastwood is dealing with the stories of assassins, thieves, and deserters for whom the films frequently encourage us to root and cheer on.

There is not a single film in Eastwood’s first twenty that doesn’t contain at its core a complicated moral dilemma, most especially in the westerns and cop thrillers, and it’s much of what makes his work so interesting overall, even when the individual entries are sub-par.

The Ones You Shouldn’t Miss

The “man with no name” trilogy which launched Eastwood’s cinematic career is highly deserving of the attention it receives (with The Good, the Bad, & the Ugly getting the most recognition, although my personal favorite was For a Few Dollars More). But if someone wanted to separate out the best from the rest, here are my recommendations of the five films you should seek out to get a well-rounded picture of his early career:

For a Few Dollars More

I’m likely to be court-martialed for this, but I still say this is a stronger film than The Good, the Bad, & the Ugly. The sheer scope and grandeur of GB&U give it tremendous credibility, but For a Few Dollars More is tighter, more suspenseful, and pushes nearly all of the same entertainment buttons (not to mention that it features the trilogy’s most compelling villain in Gian Maria Volonte’s volcanic performance). Ideally, the entire trilogy deserves to be seen, but all of the best elements of its power are on prime display in this middle chapter.

Kelly’s Heroes

It’s far from essential. Heck, it’s barely important. But Eastwood’s early films are populated with either westerns, thrillers, or mission films, and the best of that third category in my opinion is Kelly’s Heroes. What primarily makes it work so well is the outstanding supporting cast (Donald Sutherland, Don Rickles, Telly Savalas, etc.). Eastwood himself is not even that prominent in the most memorable moments, but the overall impact of the film is fun and entertaining and if you want to experience some of the ensemble adventures that Eastwood chased after in a handful of these early films, give Kelly’s Heroes a look.

Play Misty for Me

Clint Eastwood’s directorial debut is extremely impressive. It benefits from not being terribly ambitious, but it is still a tightly wound, deeply tense suspense thriller that maintains every inch of its power nearly fifty years later (thanks in large part to the phenomenal performance by Jessica Walter). I would recommend this film even apart from the interest in Eastwood’s filmography because it’s such a powerfully effective work of minimalist filmmaking. And I would, without qualification, consider it essential viewing for any fans of suspense thrillers. It’s great. Watch it.

Dirty Harry

The original film that launched Eastwood’s most extensive franchise is unquestionably one of the most affecting films of his career. Directed by Eastwood friend and mentor Don Siegel, the film represents so much of the themes and characteristics of Eastwood’s appeal as a performer and persona. Harry Callahan remains one of the benchmarks for tough, take-no-crap heroism that culturally even rivals the strongest work of Willis, Stallone, and Norris. But what makes this first film so remarkable is the complexity of its theme and the vibrance of its style. Love it or hate it, it’s hard to deny the power and impact of Dirty Harry.

The Outlaw Josey Wales

It lacks the brutality of nearly all of his other westerns. It lacks the propulsive pace of his thrillers and adventure films. But if you asked me to select just one film from Eastwood’s early years for you to watch, I would (with only brief hesitation) point you towards The Outlaw Josey Wales. At this stage in his career, Eastwood was more firmly developing his own distinct voice as a storyteller, and he had spent enough time in the genre to know where he could push the boundaries and where to hold the line. Although first-time viewers may find the episodic narrative challenging to navigate and the occasionally deliberate pacing difficult to maintain, chances are strong that the film’s more sensitive core will resonate long after the first viewing is completed. It is a film with as much heart as it has guts and a troubled soul anchored deep within its story that is nearly impossible to dismiss. And despite some stellar other entries, The Outlaw Josey Wales gets my vote for the best film of Eastwood’s first third.


Reed Lackey is based in Los Angeles, where he writes and podcasts about film and faith. His primary work is featured on the More Than One Lesson website and podcast, as well as his primary podcast, The Fear of God (which examines the intersection between Christianity and the horror genre). Follow him on Twitter or on Facebook to receive updates on his reviews and editorials.

The Evolution of Eastwood: THE ENFORCER

THE ENFORCER (1976)

“You laugh at me, you bastard, and I’ll shoot you where you stand.” – Kate Moore

“Dirty” Harry Callahan is at it a third time. This time around, we get a tease of some unconventionality; but we ultimately wind up with the same old formula, which by this time is growing a bit stale.

Eastwood had every intention of helming the director’s duties for The Enforcer, but having overtaken directorial duties for The Outlaw Josey Wales (in a somewhat controversial move which you can read about in my review of that film) left him without enough time to prepare to direct again so soon. Instead, Eastwood made a rather clever decision to promote his longtime assistant director James Fargo to fully helm the film. The partnership allowed Eastwood to ease back on the responsibilities, promote a longtime collaborator, and still manage to maintain control of the production given the longstanding dynamic between him and Fargo. The resulting production was very smooth and efficiently run.

The plot this time revolves around a domestic terrorist who kidnaps the mayor. Callahan, having lost yet another partner, is teamed up with newcomer Kate Moore (played by Tyne Daly), who was hired because of affirmative action on the behalf of gender diversity. Callahan has strong reservations against working with a woman, but Moore eventually earns his respect when she displays integrity at the cost of a promotional award. The pair of them step right up to the edge of romance, but their partnership is cut short before things can come to fruition between them, resulting in a bittersweet victory in what was intended to be the final Dirty Harry film.

There are a handful of merits to the film, primarily revolving around Daly’s performance and the performance of Albert Popwell as a gang leader informant with complex motivations. But rumor has it that the original scripts focused more deliberately on character work, which made Eastwood nervous that audiences would reject it without more action sequences. I would have loved to have seen the resulting film from those more character-centric treatments, as one of the largest criticisms I have for the film is its formulaic treatment of decisively unformulaic characters. There are at least four fascinating characters introduced in this film, not to mention the compelling elements of Callahan himself, which are painfully treated with clichés and predictable ends.

Fans of the more procedural variety of cop thrillers may genuinely enjoy this, and there’s enough of the classic Dirty Harry vibe to satisfy fans of the first two installments, but given the rich style of the first film and the thematic deepening of the second film (and most especially following right on the heels of the powerfully complex film The Outlaw Josey Wales), The Enforcer feels very much like it’s phoning in too many of its elements. It’s not bad, it’s just not very good. Eastwood is as dependable as ever, but he isn’t bringing much complexity to the character – Callahan feels more plastic in this film than he has in either of the previous two installments, which is disappointing.

Particularly disappointing is the treatment of Moore, a treatment which caused Tyne Daly to turn down the role no less than three times before ultimately being convinced to accept it. Both in Daly as a performer and in Moore as a character, there was an opportunity in this film to make some fascinating statements about women in traditionally male-dominated roles (which would have come quite a long way in righting the ship for the treatment of women in Eastwood’s filmography as a whole). But sadly, the choices made are mostly the less interesting and more common ones, especially where the film lands with the character. It may be a bit harsh of me, but in my opinion Daly’s talents are wasted here. She’s an immensely compelling performer and a master of subtle strength. It’s a real shame to think about what she might have given us in this role with a bit more liberty from the script.

It’s easy to see why this film was intended to be the final Dirty Harry film (spoiler alert – it isn’t). There is a certain weariness, both to the character of Harry Callahan and the now-predictable formula of his perils (and the terminal perils of whoever is unlucky enough to partner him). It makes this film a little difficult to recommend, and certainly not the first place to start in the Dirty Harry franchise. Although the film does have some familiarity that fans of the genre will enjoy, it’s an otherwise largely forgettable entry both in its sub-genre and in Eastwood’s filmography.


Reed Lackey is based in Los Angeles, where he writes and podcasts about film and faith. His primary work is featured on the More Than One Lesson website and podcast, as well as his primary podcast, The Fear of God (which examines the intersection between Christianity and the horror genre). Follow him on Twitter or on Facebook to receive updates on his reviews and editorials.

The Evolution of Eastwood: MAGNUM FORCE

MAGNUM FORCE (1973)

“I hate the —— system! But until someone comes along with changes that make sense, I’ll stick with it.” – Harry Callahan

It was barely two years after Dirty Harry that Eastwood would strap on the signature .44 Magnum once again as Harry Callahan in Magnum Force. The results can’t help but be measured up against the original, in both positive and negative ways.

Picking up sometime shortly after the events of Dirty Harry (a fact only identifiable by a single reference from Harry about his last partner), Harry Callahan (Eastwood) has been relegated to stakeout detail by the stubborn and irritable Lt. Briggs (Hal Holbrook). However, someone in the city is taking justice into their own hands by murdering accused criminals who escaped the system through wealth or technicalities. When the evidence begins to point towards a group of vigilantes on the police force, Harry determines to uncover the truth and bring them to justice himself.

The film was largely an extension of unused material from the first film and a response to some of the criticisms and controversy that film generated. Eastwood wanted to make it clear that Callahan’s character was not a lawless vigilante, so building upon an idea first introduced by Terence Malick into his version of the Dirty Harry script, a script was commissioned by future director John Milius, with eventual rewrites by Michael Cimino. Eastwood was offered the director’s chair, but declined, which was a puzzling choice given what would become on-set tensions between he and Ted Post, someone who had directed Eastwood multiple times on Rawhide and had helmed the solid western Hang ‘Em High.

The final film caused considerable tension among its creators regarding the finished product. Writer John Milius all but disavowed it, citing the changes to the final act and the heightened violence from his original drafts as veritably ruining his original intentions for the story. In addition, director Ted Post cited multiple conflicts with Eastwood, who he claimed was frequently disputing who was truly in charge on set. Post accused Eastwood of exerting ego and leveraging control on set rather than allowing him to do his job. When the two of them had last collaborated, Eastwood’s star was only just rising in America and his directorial confidence didn’t exist yet. Although Eastwood himself had actively turned down the director’s duties for Magnum Force, it would appear that letting go of the role was harder than initially expected. Post and Eastwood would never work together again.

When viewed on its own merits, Magnum Force is a perfectly entertaining police thriller. The performances, particularly by Eastwood and Holbrook are strong as well as a solid showing by Felton Perry as Eastwood’s new partner. It also features a who’s-who of sorts for soon-to-be stars of the 70s including David Soul, Tim Matheson, and Robert Urich. It also effectively highlights Harry Callahan’s skills as a detective, something the original film didn’t emphasize as much as his boldness or attitude. In direct contrast to the vigilantism of which Callahan’s character was accused in the original, there is a deliberate and occasionally heavy-handed emphasis in this film to show that Callahan IS a part of the system and has no tolerance for predatory vigilantism (I’ll leave it to others to determine the level – if any – of hypocrisy at play in these assertions).

What’s sadly missing, unfortunately, are the strong senses of style and suspense that Dirty Harry had in spades. Magnum Force, for all its narrative merits, feels very paint-by-numbers stylistically. This isn’t wholly unexpected when considering that the bulk of Post’s directorial work had previously been for television, where a somewhat formulaic template might be seen as a necessity of continuity. The film’s major reveals will largely be guessed long before they are revealed, making their ultimate result feeling rather inevitable as well, which undermines the suspense factor.

There would be three more sequels in the Harry Callahan world, all of which would suffer from the common sequel problems. But as far as sequels go, Magnum Force isn’t bad. Eastwood even later cited it as his favorite entry in the franchise (which is interesting given that Eastwood eventually directed one of them). If you’re hoping to experience the same level of fascination and compelling storytelling that Dirty Harry brought, you’ll likely be at least slightly disappointed, but if you’re feelin’ lucky… give it a shot.


Reed Lackey is based in Los Angeles, where he writes and podcasts about film and faith. His primary work is featured on the More Than One Lesson website and podcast, as well as his primary podcast, The Fear of God (which examines the intersection between Christianity and the horror genre). Follow him on Twitter or on Facebook to receive updates on his reviews and editorials.

The Evolution of Eastwood: DIRTY HARRY

DIRTY HARRY (1971)

“Being that this is a .44 Magnum, the most powerful handgun in the world and would blow your head clean off, you’ve gotta ask yourself one question: ‘Do I feel lucky?’ Well do ya, punk?” – Harry Callahan

There are two roles for which Clint Eastwood is most prominently known: the “man with no name” from the Sergio Leone westerns and “Dirty” Harry Callahan.

It’s ironic, then, to consider that he not only wasn’t the first choice for the role, he wasn’t even among the first 10 choices. The role was offered to stars like John Wayne, Steve McQueen, Paul Newman, Burt Lancaster, and even Frank Sinatra (who was attached to it for the longest period of time prior to Eastwood). The script (originally titled Dead Right) had been bouncing through development for several years and under several different talent packages before (rumor has it) Paul Newman recommended that Warner Brothers reach out to Clint Eastwood.

Eastwood was in post-production on Play Misty for Me when the original script was sent to him, but by that time the script in development had been in several hands (including a draft by John Milius and one from Terence Malick) and Eastwood did not like the new versions as much as the original. He also insisted that Don Siegel direct the film and even approached Universal executives to get Siegel loaned out for the director’s chair.

Dirty Harry is about a San Francisco police officer (and dedicated to officers who have died in the line of duty) whose nickname comes from the fact that he’s always handed the “dirty” jobs no one else wants to touch. He also has a reputation for using unconventional tactics – which frequently get him and the police force into trouble – to bring criminals to justice. When he begins to close in on a serial sniper wreaking havoc throughout the city, tensions escalate and the department comes under immense scrutiny to both catch the killer and abide by the procedural guidelines. Harry is caught in the crossfire of these two objectives, and you can easily guess which one of the two he cares most about achieving.

Dirty Harry is not only a landmark, signature entry in Clint Eastwood’s career, it is a landmark entry in the crime genre at large. Of the five collaborations Eastwood and Siegel had as director and star, Dirty Harry is easily Siegel’s most stylish film, exploring interesting setups of shadow and color as well as experimenting with differing suspense techniques as well (which would be mimicked by countless police thrillers that followed). The character of Harry Callahan provides an opportunity for wry moments of dark humor for Eastwood (“Well do ya, punk?”) and the violence is heavily intensified from his previous cop-drama, Coogan’s Bluff (which Siegel also directed).

The film stirred substantial controversy in its initial release due to its perceived “ends-justify-the-means” philosophy and the violence (both of which were reasons cited by offered stars for turning down the role). But the film also sparked significant conversation about victim’s rights, which was a major reason why Eastwood wanted to make the film in the first place. The social dialogue intensified around police brutality and questions of procedural responsibility as well.

And although those concerns remain vital points of conversation almost 50 years later, it’s hard not to be plainly and simply impressed by how affecting of a film Dirty Harry is. While other crime thrillers from the same era have disappeared into the status of “relic”, there is a vitality and a potency in Dirty Harry that still thrives. Much of that is owed to Eastwood’s assured and confident performance (strapping back on the gun he left behind for two films – and taking an upgrade while he’s at it), but a tremendous portion of why the film works so well is creditable to Don Siegel’s approach to the picture. By this point, he and Eastwood were such a formidable collaborative machine that it’s quite surprising that they wouldn’t make another film together for 8 years.

It is now pretty widely known that Eastwood himself directed at least one prominent scene in Dirty Harry, and he possibly stood as a secondary directorial surrogate for Siegel on other scenes as well. But whatever cocktail this pair of creatives had drank down, it was electric by this point.

1971 saw three collaborations between Siegel and Eastwood (two of which Siegel directed and Siegel also played a small, bit role in Play Misty for Me) and all three of them are fantastic. The Beguiled is disturbing and fascinating and Play Misty for Me is a nail-biting suspense thriller, but easily the most culturally iconic (and objectively best) of the three films is the indomitable Dirty Harry. It’s a standard-setting film in the cop-thriller genre and one that should not be missed by any remote fan of that brand of story.


Reed Lackey is based in Los Angeles, where he writes and podcasts about film and faith. His primary work is featured on the More Than One Lesson website and podcast, as well as his primary podcast, The Fear of God (which examines the intersection between Christianity and the horror genre). Follow him on Twitter or on Facebook to receive updates on his reviews and editorials.