Film

The Trials and Tribulations of "Dirty" Harry Callahan

Feeling lucky, punk? The road from obscurity to legend wasn't easy for Clint Eastwood's iconic character Dirty Harry. Think you know the back story? Read on!

Who is filmdom’s most iconic screen cop? What character laid the groundwork for virtually every "loose cannon" detective whose ends justify his means? Who is arguably the most quotable badass ever to stalk the streets of San Francisco (all the while keeping them safe from crime)?

If you said "Jack Webb", then you’re probably either joking or you’re my late grandfather (which means I really need to get rid of this Ouija board next to me). If you said "Dirty Harry" then consider that Kewpie Doll your own, mister.

"Dirty" Harry Callahan is an undeniable screen icon. Having kicked ass in no less than five films between 1971 and 1988, he brought a new level of both realism and violence to the police procedural and marked one of Clint Eastwood’s most recognizable roles. Indeed, Harry Callahan could be considered Eastwood’s signature character if the actor hadn’t starred in so many memorable parts before, during and after his bow as the California detective. Because Eastwood rarely plays the same character twice (in name, anyway), the case for a signature character is both easy to make and violently punctuated by six shots from a .44 Magnum.

Bringing the angry whisper and grim visage of his already cultivated "Man With No Name" character, and creating lines that have become classically quotable film references along the way, Eastwood may have been born to play the role of the edgy investigator. That’s easy for us to say now, but old Clint was hardly the first choice for Callahan. Nor was he even the second or third or even on the short list of actors. This is hardly the only absurdity in the evolution of the Dirty Harry saga. In fact, looking at what the original film and its now-iconic title character could have become, it’s a shock that audiences have been gifted a film series this legendary and high quality.

Harry Callahan started life as a character in a screenplay entitled Dead Right. That screenplay was the late '60s product of writer Harry Julian Fink (well known for such works as the 1957 – 1963 TV Western Have Gun – Will Travel) and his writing partner and wife Rita M. "R.M." Fink (with whom he also wrote 1971’s Big Jake and 1973’s Cahill U.S. Marshal, both starring John Wayne). Dead Right was about an aging New York detective named Harry Callahan who faced burn out in his late 50s, but became obsessed with stopping a serial killer named Travis who was preying upon the city. In the original version it wasn’t even Harry who took the bad guy out in the end.

Draft after draft was attempted as the Finks and their production cohort Jennings Lang attempted to find the perfect actor to fill the role of the older policeman. Unsurprisingly, the original offer for the film went to John Wayne, whom the Finks had written the part specifically for. Wayne, however, felt that the violence in the film was glorified and unjustified, so he passed on the project. Still, using Wayne as the example of how they wanted Callahan to turn out was good enough for Universal Studios to option the screenplay from the Finks. The studio even envisioned Clint Eastwood in the lead, but the project languished in "Development Hell" until the screen rights ran out and returned to the Finks.

When Universal lost its rights to the project and the hunt for an appropriate actor to fill the role proved frustrating, Lang actually sold the rights to ABC Television with the idea of producing a TV movie of the week. Can you imagine the violent warpath of Dirty Harry toned down for the tube (of that era)? Neither could ABC, apparently. Feeling that neutering the hard-edged film would destroy the best parts of it, ABC backed out and the rights were re-sold to Warner Bros.

Once Warner Bros. stepped in, it quickly put its own vision on the cop crusader. Warners’ choice was not Eastwood, nor was it "The Duke", but Ol’ Blue Eyes himself, Frank Sinatra. As odd as it may seem to picture Dirty Harry scatting a loud "Doo-be-doo-be-dooooooo!", Sinatra was indeed very interested and went as far as contract negotiations with Warner Bros. For those of you still in disbelief, please note that Sinatra did star as the title role in The Detective (1968) wherein he played the role of Joe Leland. Bruce Willis would later play the same role (albeit renamed to "John McClane") in the Die Hard series of films, starting in 1988. (See the Next Reel article "Out of Sequence: The Saga of Hollywood's Hidden Sequels" for more on that story).

The studio was quite keen on sealing the deal to ink the then 55-year-old Sinatra as the man behind the Magnum. Thus, it brought in veteran director Irvin Kershner (who would go on to helm 1980’s The Empire Strikes Back) and the hottest young screenwriting name in John Milius (who would go on to write 1979’s Apocalypse Now). Milius insisted that Warner provide him with a version of the .44 Magnum that the character would be using, for inspiration. He turned in the Sinatra-seducing script in just 21 days.

However, this same gun was partially responsible for Sinatra passing on the role. Having broken his wrist on The Manchurian Candidate (1962), Sinatra found the "hand cannon" that the Magnum actually was to be too unwieldy to convincingly fire. Having also faced the death of his father not long before, Sinatra was eager to seek out lighter fare as opposed to the dark and violent tale that would become Dirty Harry.

Realizing that this meant that its own Dirty Harry would never meet "The Girl from Ipanema" in this film or any of its sequels, Warner Bros. widened its net, hoping to catch a big enough star to make Dirty Harry a success. Marlon Brando was briefly considered (though he reportedly was never made an offer) before Robert Mitchum was given the chance to play the role.

At the time, Mitchum had a rule that the less he liked a script the more money he would demand and the studios always tended to pony up. Mitchum, however, found Dirty Harry to be so deplorable that he would not accept the part "for any amount", considering it to be one of the "movies that piss on the world" and "a piece of junk". Mitchum added "If I've got $5 in my pocket, I don't need to make money that fucking way, daddy." Thus the man who played a serial killer in such films as When Strangers Marry (1944), The Night of theHunter (1955) and Cape Fear (1962) felt that Dirty Harry was too much for him. He turned down the lead role in the seven Academy Award winning film Patton (1970) for similar reasons.

On the other hand, Robert Mitchum’s brother, John Mitchum, did appear in the first three Dirty Harry movies, which may have made for some awkward Thanksgiving table conversations.


Burt Lancaster, Steve McQueen and Paul Newman were all approached to play Dirty Harry, and all of them turned the role down down, although Newman recommended 41-year-old Eastwood for the part. Warner Bros.’ response translates to something along the lines of “Okay, sure, why not Clint?”

Yes, folks, this is arguably Eastwood’s most recognizable role and he was the studio’s eighth choice. Am I the only one imagining Eastwood’s Paint Your Wagon-esque rendition of the song “I'm Henery the Eighth, I Am”? Probably… but still… Eighth Choice? Clint?

At last Warner Bros. offered Eastwood the role and he accepted it under the provision that he would also be able to produce through his own Malpaso Company production corporation. The announcement was made in the press just before Christmas of 1970. From that point, Eastwood maintained an almost Dirty Harry-esque amount of control over the production.

Having first seen the script back in 1969 when Jennings presented it to him (while the project was still at Universal) Eastwood was already intimately familiar with the early stages of the project. Believing that the rewrites had ruined the point of the entire story (to be fair, some versions demoted Harry to a cameo by the last act of the film as Marine snipers took out the bad guy), Eastwood proclaimed "I'm only interested in the original script" and he demanded rewrites.

Another of Eastwood’s provisos was that Don Siegel direct the film. While Eastwood himself was tied up in post-production on his directorial debut Play Misty for Me (also 1971), Siegel was locked into a contract with (you guessed it) Universal Studios, which prevented his involvement in a Warner Bros. picture. Undaunted, Eastwood went to the studio heads at Universal and requested that Siegel be loaned to Warner Bros. for this film. Based, in part, on Eastwood’s success with director Siegel on yet another 1971 film, The Beguiled, Universal agreed and Eastwood (and the Warners) had their helmsman.

Siegel further agreed with Eastwood on the scripts and the duo rejected them all. The villain, now renamed "Scorpio", was to be a mindless killing machine who committed psychopathic murders simply because he liked to, but Milius’ successor Terrence Malick had upgraded Scorpio into an anti-heroic vigilante who killed wealthy criminals who had escaped justice. Siegel hated the idea and Eastwood agreed that it wasn’t right for the first film, but the story stuck with him and he decided later to revisit the concept.

Eastwood and Siegel hired Dean Riesner to rewrite the screenplay. At Eastwood’s instructions, Riesner used the original Fink and Fink script as the basis for the film with some biting (and quotable) dialogue from Milius’ version kept in and reshaped the plot into a retelling of the real-life saga behind the Zodiac Killer who had stalked the same San Francisco Bay Area that Scorpio would in the film, only a few years before. Detective David Toschi (the chief investigator in the Zodiac case) was even used as a partial inspiration for Callahan himself.

Although the inspiration for the killer was intact, Eastwood, Siegel and Warner Bros. found the villainous and sociopathic character of Scorpio almost as hard to cast as Dirty Harry himself had been. James Caan had also been attached to the role going back to the Sinatra and Kershner days, but he didn’t feel quite right as a match for Eastwood, so the star and director kept looking. Siegel pushed for Audie Murphy to play Scorpio, feeling that having the clean-cut genuine war hero and screen icon play a psychopathic killer would create a delicious irony. That irony was sadly trumped by another as Murphy died in a plane crash before discussions could be finalized.

Eastwood had seen Andrew J. Robinson in a stage performance of Subject to Fits and envisioned the actor as the disheveled, psychologically unbalanced hippie that Scorpio became. Upon seeing Robinson, Siegel readily agreed, believing he had his "irony" angle covered with Robinson, whom Siegel described as having "a face like a choirboy". Thus, Dirty Harry finally had its perfect villain, right?

Well, not exactly.

The "Choirboy" angle wasn’t far off for Robinson. Those who best remember Andy Robinson as the duplicitous Garak from Star Trek: Deep Space Nine (1993 – 1999) or licking blood from his lips and gleefully growling "Jesus Wept!" before being torn apart by hooks and chains in Hellraiser (1988), not to mention his eventual sadistic turn in Dirty Harry itself, may be shocked to learn that two words accurately used to describe the actor have been "squeamish" and "pacifist".

Robinson detested the use of firearms in real life and could barely cover his discomfort on film, flinching violently every time his gun was fired. Disturbed by this revelation, but still convinced that Robinson was the best choice, Siegel actually shut down production completely and sent Robinson to classes in order to learn to fire a gun convincingly. While this did work, the astute viewer will still notice Robinson’s eyes closing every time the trigger is pulled.

Robinson was also very uncomfortable with the character’s bigotry, chilling at the use of racist epithets in the film and he absolutely hated having to berate and physically abuse school children in the finalé of the film. Possibly as part of a calming ritual, Robinson’s real-life stepson, Steve Zachs, was chosen to portray one of Scorpio’s hostages.

However squeamish or pacifistic Robinson may be, he is also a very fine actor and his performance has proven to be one of the biggest reasons that Dirty Harry became such a success. Although Milius gets credit for many of the film’s best lines, such as "You have to ask yourself one question: 'Do I feel Lucky?' Well DO YA, PUNK?", Robinson actually adlibbed many lines that remained in the final product. The line "My, that's a big one!", uttered when Dirty Harry first shows Scorpio his gun evoked laughter in the crew, causing the scene to have to be re-shot. However, Siegel loved Robinson’s adlib so much that he had him repeat it for the final cut. "Hubba, hubba, hubba, pig bastard!" was also an adlib on Robinson’s part.

This cop film that had more misfires than any marksman would tolerate, and actually came together remarkably well, thanks to the writing, directing and acting of the well-chosen team that ultimately made Dirty Harry (1971). Released in December 1971, Dirty Harry was a remarkable success, earning $36 million in its initial run against a mere $4 million budget, making it the fifth biggest box office earner of the year. Unsurprisingly, however, the film caused controversy upon release due to its intense violence (it was an envelope pusher for the time). Debates over victim’s rights, police brutality and the nature of law enforcement helped to propel the controversy. At the 44th Annual Academy Awards, feminist groups protested the film, with slogans echoing Robinson’s own, such as "Dirty Harry is a Rotten Pig!"

Although considered a critical darling today, Dirty Harry received mixed reviews in its initial run. Many critics praised the film, particularly Eastwood’s performance, while others, such as Roger Ebert, denounced the film as "fascist". Today, Dirty Harry holds a 95 percent approval rating on RottenTomatoes.com, and is considered one of the best films of 1971. The film continues to appear on "best of" lists and has proven to be among the most influential films of all time. Many actors, such as Arnold Schwarzenegger and Robert Urich (who latter appeared in the first sequel) cite Dirty Harry as among their biggest influences. For better or for worse, the .44 Magnum enjoyed an upswing in sales after this film’s debut.

Notably, John Wayne, whom this part was written for, regretted having passed on the part and went on to make two Police films McQ (1974), and Brannigan (1975), reportedly spurred on due to the success of Dirty Harry.

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