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!

How's Dirty Harry Feeling These Days?

Diversifying his resume greatly, Eastwood then starred as a cop in the Warner Bros./ Malpaso Company production known as City Heat (1984) in which he plays a cop named Lieutenant Speer who shares so may traits with Harry Callahan that his performance qualifies as a spoof in this comedy film.

Dirty Harry aged with time, and always felt just a little bit outside of whatever time he found himself in.
By the mid-'80s, Dirty Harry was as hard to escape from as Eastwood’s own "Man With No Name" persona (which he also dusted off a few more times for various projects). In case you couldn’t tell, Eastwood had lots of fun going back to Dirty Harry and characters like him, so for 1988’s The Dead Pool, Eastwood decided "I'll go back and see how he feels about things now."

To this end, Eastwood ran with an idea thought up by three of his buddies from the health and fitness scene. Sandy Shaw, Durk Pearson and Steve Sharon came up with the idea of a list of celebrities whose deaths could be predicted and bet on… and a serial killer who finds the list and decides to make it come true. While Shaw and Pearson had both advised on films before (including some of Eastwood’s own), neither of them had any writing credits to their name. To date, The Dead Pool remains their sole credit of this kind. Sharon, who actually wrote the screenplay based on the story he created with Pearson and Shaw, had no other movie credits to his name and The Dead Pool remains his only credit of any kind to date.

Aspiring writers, once again, take note: no matter who you are or what your experience level might be, Eastwood probably wants to read your script.

Controversy was never far off from the Callahan character and protests began even before filming commenced. Believing that "Dirty Harry" was not a very good representative of San Francisco, citizens took to the streets to attempt to convince the city to deny filming permits for the production. If that seems a little over-the-top then you should see The Dead Pool.


By 1988, the style of cop films that Dirty Harry had sired had gotten both more extreme and more comical. Lethal Weapon (1987) pushed the envelope in both categories and The Dead Pool itself debuted in theaters less than a full week before the next phase in action flicks, Die Hard hit (and blew up) silver screens the world over. Writer Steve Sharon and director Buddy Van Horn recognized the debt owed to Dirty Harry and worked toward fitting that film’s title character into the new world of action cinema.

Liam Neeson stars as glitzy Hollywood director Peter Swan, while Patricia Clarkson takes her bow as a popular television journalist. Even Harry Callahan himself becomes something of a celebrity after testifying against a mob boss, sending him to jail, and then cooperating with the media.

Perhaps most humorously, Jim Carrey is cast as Johnny Squares, a drug addicted rock star who lip synchs to Guns N’ Roses’ "Welcome to the Jungle" (in an over-the-top performance that could only be done by Carrey). This video shoot is for the Film-Within-A-Film called “Hotel Satan”, which Squares’ song is intended to be a tie-in with. As life imitates art, the release of Guns N’ Roses' Appetite for Destruction was pushed forward in order to provide a more valid marketing tie-in with the film. Trailers for the film featured the song, which helped to promote the band and the popularity of the song helped promote the film.

Members of the band Guns N’ Roses, though not seen performing their own song, also have cameo appearances in the film. Particularly notable is the scene in which guitarist Slash fires a harpoon through a window, much to the chagrin of Neeson’s director character. Considering the immense popularity that Guns N’ Roses soon enjoyed, Carrey’s performance (which is about five kinds of nothing like Axl Rose’s own) is particularly hilarious.

For those of you objecting and pointing out Carrey’s prowess in his first ever “serious role”, please note that the comedian won the role specifically due to comedy, not drama. Carrey’s audition did not consist of acting out scenes for the movie, but performing Elvis Impersonations for Eastwood. Eastwood and colleagues were reportedly laughing hysterically and thus, young Jim got the part.

Reportedly, Steve McQueen passed up the lead role in the first Dirty Harry film because he didn’t want to make another cop film after Bullitt (1968). Interestingly enough, The Dead Pool features a tribute to Bullitt in its car chase scene. The fact that Callahan’s car is being chased by a remote controlled toy car is both epically amazing (especially from a technical standpoint) and somewhat hard to believe at the same time. The scene is incredible to look at and shocking in its execution (it is reportedly Eastwood’s own favorite scene in the film), but at some point it’s hard not to think "Dude, am I watching a Dirty Harry flick where the star is being chased by an explosive toy?"

For all of its flaws, The Dead Pool still manages to be a good and exciting film with a typically badass performance by Eastwood and a surprising "whodunit"-style mystery that still holds up. However, reaction was mixed from both critics and audiences (not to mention Guns N’ Roses fans). While both Roger Ebert and Gene Siskel gave this fifth film positive reviews, agreeing that it was the best film of the series since the first, it didn’t quite achieve the critical acclaim of other films in the series. While the previous film had more than tripled its $22 million budget and became the most successful film in the series, The Dead Pool made less than $38 million against a budget of $31 million. Not exactly a flop, but far from a blockbuster.

In contrast, Die Hard, which competed with The Dead Pool in many of the same theaters, went on to make over $140 million against a $28 million budget and has spawned four sequels to date.

Sequels would not be in the cards for Dirty Harry, although the relative underperformance of the film is not the reason why. Eastwood has been open about the series having run its course and believed that any films he would make after this one would become parodies due to his age (58 at the time of The Dead Pool’s release). This is, of course, ironic, considering the fact that the original film (released almost 17 years prior) had been written with an actor in his late 50s in mind for the lead. Still, Eastwood scoffed at the idea of any further sequels and still laughs at the idea of “ Dirty Harry VI: Harry Is Retired”. The actor jokes about a retired Harry tiring of using a fly fishing pole and deciding to use his signature .44 Magnum to shoot the fish, instead. Eastwood further facetiously predicted a film in which Callahan would chase and catch criminals using a walker.

Instead of further films, a 1990 video game entitled Dirty Harry (alternately known as Dirty Harry: The War Against Drugs) was created for the Nintendo Entertainment System. This side scroller pits Harry against the drug lords of San Francisco and features Eastwood’s face from the Sudden Impact poster on the packaging, but did not feature any actual contributions from Eastwood. A Dirty Harry pinball machine (packed with electronic quotes) was created by the Williams Manufacturing Company (WMS Industries) in 1995.

A second video game, tentatively entitled Dirty Harry was planned by Warner Bros. Interactive and game developing company The Collective, Inc. for release in 2007. This game, planned for the Xbox 360 and the PlayStation 3, would have been an official series entry taking place between Dirty Harry and Magnum Force. It would have featured an actual performance by Clint Eastwood in voice and likeness, and he would have also benefitted from his creative input. Plans included more depth for the character and an exploration of the man behind the gun. Sadly, undisclosed trouble at The Collective caused the game to be permanently cancelled, though a Facebook group has arisen, attempting to urge Warner Bros. to complete and release the game.


Eastwood went on to even greater successes, including Oscar nominations and wins, starting with 1992’s Unforgiven (which featured something of an "all grown up" version of "The Man With No Name"). In 2008, Eastwood directed and starred in the action / adventure thriller Gran Torino, and rumors in the press and online circulated to suggest that this film was secretly to be the sixth and final film in the Dirty Harry franchise. There was no confirmation as to whether the supposed film would have included scenes of Harry shooting fish or catching bad guys with his walker, but the biggest speculation surrounded retired police detective Harry Callahan tracking down a killer who drives a Ford Gran Torino around town and kills people, one of them Callahan’s own grandson.

Such rumors could never be substantiated, as the stories surrounding the connection between Gran Torino and Dirty Harry proved to be untrue. Still, critics noted the similarities between Eastwood’s Walt Kowalski character and "The Man With No Name" and Dirty Harry Callahan.

Gran Torino wasn’t the first time critics noted similarities between Eastwood’s characters and Callahan. Aside from the aforementioned Tightrope and City Heat, Malpaso and Warner Bros., teamed up again with director and star Eastwood for the 1990 cop buddy film, The Rookie. Critics and audiences saw Eastwood’s character of Nick Pulovski as a thinly veiled representation of Harry Callahan training a young cop to follow in his footsteps. Variety actually referred to The Rookie as "Dirty Harry 5 1/2", although not exactly meaning it as a compliment.

Dirty Harry lived on in a series of 12 novels published by Warner Books and credited to Dane Hartman (a pseudonym shared by authors Ric Meyers and Leslie Alan Horvitz). The novels became almost as popular as Jerry Lewis in France when French writer Jean-Paul Schweighaeuser translated them for publication on the continent as the Collection Supercops novel series.

An unauthorized novelization came from the pen (and easel) of writer/ artist Frank Miller, famous for such graphic novels as DC Comics’ Batman: The Dark Knight Returns, a number of redefining Daredevil issues for Marvel Comics and his own series Sin City for Dark Horse comics. When Miller, already a huge star for his comics work, saw The Dead Pool he was disgusted and didn’t consider it worthy to be the last Dirty Harry story. In response, Miller created the famous Sin City story That Yellow Bastard in which aging detective John Hartigan stands in for Harry Callahan as he defends and avenges a young girl named Nancy. In 2005 the feature film Sin City was created based on the comic books, including That Yellow Bastard. Die Hard’s own Bruce Willis stepped into the role of Hartigan (and, by proxy, Dirty Harry) and for the film version, Nancy was given the last name "Callahan".

Unlike most huge franchises out there, there has been no attempt to actually reboot the Dirty Harry series, possibly due to the iconic stature of its leading man. After all, do we really have any valid Clint Eastwood stand-in out there? Any actor who played the part exactly the same would be criticized as unoriginal and farcical, while any actor who brought his own attitude to the role would be criticized as being nothing like the original and borderline blasphemous. In short, there is only one Clint Eastwood.

While I, and probably you, could think of a few actors out there capable of making the role their own and still honoring the past, perhaps having only these five films is really for the very best. Dirty Harry is not James Bond or Batman whom various actors can play whenever the franchise needs fresh blood. Dirty Harry aged with time, and always felt just a little bit outside of whatever time he found himself in. In this age of rampant remakes, reboots and recasting, shouldn’t we have a franchise or two that remain influential and infinitely watchable but not at all able to be recreated?

This inability to recast Dirty Harry with anyone besides Eastwood is both appropriate and humorously ironic. Eastwood was not intended to play the character of Dirty Harry Callahan and was in fact the eighth choice for the part. Once given control of the character, however, he made Dirty Harry his own to the point that it's almost impossible to imagine any other actor playing the role. Whereas the character was originally written and intended for John Wayne, that actor would have been 64 years old when his Dirty Harry was released. Eastwood left the part permanently at age 58 which was just about the age the Finks originally intended Harry Callahan to be in the first film. Regardless of the original intent, Clint Eastwood and Harry Callahan are, and ought to be, completely inseparable.

Is there any future for the franchise in any form? I, personally, would belly up to the box office to see another Eastwood Dirty Harry flick, regardless of age, even if the film consisted of Harry Callahan debating an empty chair in front of a political convention. Until that happens, I’ll see you in The Next Reel.

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