You’re Out of Bullets: Dirty Harry Calls it a Day with The Dead Pool

The archetypal vigilante hangs up his holster in Eastwood’s fourth and final Dirty Harry sequel

When last we saw Dirty Harry in 1983’s Sudden Impact, San Francisco Police Inspector Harry Callahan was a changed man. Faced with a complex situation in which there seemed to be no common ground between justice and the law, Harry sided with a vigilante out to avenge a brutal gang rape she and her sister suffered years before. He also fell in love with the woman, played by Sondra Locke, Clint Eastwood’s real-life girlfriend at the time. They walked off into the sunrise together, accompanied by Lalo Schifrin’s melodic yet somber end credits music, which itself had become a mainstay in the franchise by that point. Watching this movie at any time up to the summer of 1988, one could not help but get the feeling that we had just seen the last of Dirty Harry. It was assumed that he would settle into his retirement years with a woman by his side and a bucolic life as reward for his many years of public service. Yeah, right.

Sudden Impact could have been Dirty Harry’s swan song. The only film in the series directed by Eastwood himself, it harkened back to the darkness and emotional gravity evident in the earliest installments, Dirty Harry and Magnum Force. True, it does get weighed down in some of the tropes that grew tiring over the course of the series, namely Harry’s constant battles with authority, how he always seems to be in the vicinity when an armed robbery is taking place, and the accusations he faces about being a misogynistic, racist dinosaur. But that’s the nature of film franchises. Every successful film series must contain some element of familiarity that ties all the installments together. Kind of like how James Bond always seems to be issued just the right gadgets from Q Branch that will save his ass and the world later in the film. The supporting cast may completely change, and the stakes could be totally different than before, but audiences like being able to grab something familiar when walking into a sequel, even if they expect the film to be bigger and better than its predecessor.

It’s also the nature of film franchises to lose their zest over time. Even the most successful ones often succumb to the greed of film producers or the hubris of the creators and stars who think they have “one more left in them.” With Sudden Impact, Eastwood and company had the opportunity that very few movie franchises get—to go out on their own terms, leaving the audience yearning for more but pleased that the last installment was an entertaining one worthy of its predecessors. After the huge success of Sudden Impact, Eastwood was asked repeatedly whether he would pick up Callahan’s .44 one more time. But his response was always the same. There was no place left to take the character. He had put it out of his mind and turned his energy to other things. There would still be tough-guy roles in Heartbreak Ridge and Pale Rider, but Eastwood knew he was getting older, and action pictures would only get harder to come by. He became drawn to more personal projects, like 1988’s Bird, in which he directed Forest Whitaker as jazz legend Charlie Parker. Eastwood, a lifelong jazz aficionado, knew that the film was a commercial gamble for Warner Bros., the studio with which he had established a long, profitable relationship. So, he agreed to offset Bird’s almost certain box office loss with, you guessed it, another Dirty Harry movie.

The new film, The Dead Pool, from a script by self-help authors Durk Pearson and Sandy Shaw and screenwriter Steve Sharon, would address the allure and dangers of celebrity, putting Harry squarely in the midst of a media circus that also includes a jailed mob boss, a monumentally pretentious film director, and an ambitious local television reporter. The movie opens with Harry Callahan taking on a quartet of hitmen hired to rub him out by mob boss Lou Janero, who was recently sent to prison thanks to Harry’s police work. To no one’s surprise, Harry nails them all with his hand cannon, and later learns that he has become a local celebrity for his efforts. His superiors want him to become friendly with the media as it will generate good press for the police department, but Harry doesn’t fancy himself being part of a “dog and pony show.” Knowing that Janero won’t stop coming after Harry, even from behind bars, his boss assigns him a new partner, Al Quan, to watch his back. Quan, played by veteran character actor Evan C. Kim, is not too crazy about the assignment. He knows, like we all do, Harry’s track record with partners, who all end up in the hospital or dead.

Don’t you get it? The whole idea is to pick celebrities who aren’t going to make it because they’re old, because they’re sick, or because they’re in a high-risk profession.
Swan

While Harry and Quan hit the street, across town veteran movie director Peter Swan is filming a music video to promote his latest picture, “Hotel Satan.” Swan is a self-involved filmmaker specializing in making low-budget video nasties not unlike the classics so beloved by the writers and readers of VHS Revival. He is so full of himself that anyone within a 10-meter radius feels like they are intruding. Even his poor excuse for a ponytail is pretentious. Swan is played by a pitch-perfect Liam Neeson, who at this point in his career was still working in supporting roles. In the music video, Swan is directing druggy rock star Johnny Squares, played by Jim Carrey, another relatively unknown commodity who would later go on to become a household word. The comedian’s performance in the music video sequence is vintage Carrey, rubber-faced and thrashing about to Guns N’ Roses first hit “Welcome to the Jungle.” The band had reached superstar status by the time The Dead Pool was released, and being signed to Geffen Records, which was owned by Warner Bros., it was only logical to have the world’s most popular heavy metal band tied to a Dirty Harry film. Members of the band even make cameos in a couple of scenes later in the film, and guitarist Slash gets to fire a harpoon gun for Swan’s movie.

Squares leaves the set and retires to his trailer to shoot up. He is interrupted by an unknown guest who shoves a fistful of barbiturates down his throat, killing Squares. Harry and Quan show up to investigate, and get the characteristic brush-off from Swan, who tops his show-must-go-on attitude with a heaping helping of I-don’t-give-a-shit. TV reporter Samantha Walker shows up to get the story, cornering Squares’ hysterical girlfriend for an exclusive interview. Harry is disgusted by Samantha’s lack of compassion, snatches the TV camera, and pitches it across the parking lot. Later, he and Quan are walking through Chinatown when a man is blown away with a shotgun right in front of them. It turns out that a bunch of punks are trying to rob a restaurant, but Harry and Quan foil the crime, with Harry using his .44 and Quan using his fists and feet. They discover that the man who was killed is actually Peter Swan’s executive producer. This is one of those movie coincidences that border on laughable, but it was apparently the only way to move the film into its second act. Quan discovers a list of local celebrities in the exec’s pocket that includes Johnny Squares, who has “RIP” next to his name, and one Harry Callahan. Behold, we have discovered the dead pool.

The dead pool is a game that Swan and some members of his crew are playing where they try to guess which local celebrities will die within the year. But someone is taking the game a little too seriously and is trying to rig the outcome. When a film critic, who is also on the list and decidedly unfriendly toward Swan’s work, turns up murdered, Swan becomes a prime suspect. Harry confronts the snooty filmmaker about the list at Johnny’s funeral.

Samantha shows up at police headquarters and promises to drop her station’s lawsuit against the department over the busted camera in exchange for dinner with Callahan. What Samantha really wants is Harry’s life story. She even has a scrapbook that briefly takes us through the previous films with newspaper clippings of Scorpio, vigilante cops, and saving the kidnapped mayor. Harry refuses to play along, believing that Samantha is motivated only by the fact that he is on the dead pool list. They make peace later, though, and as they stroll along, they are attacked by another group of Janero’s hit men. Harry fends of the attack, which means more dead bodies, and then makes a trip to San Quentin State Prison to visit Janero. He recruits a hulking prisoner named Butcher Hicks to help him lay down new rules with the mob boss, telling Janero that Hicks killed three men with his teeth.

Janero is so convinced that Hicks will eat him that he hires a pair of men to act as Harry’s bodyguards. This doesn’t work out well, though, as Harry believes the men are trying to kill him and he promptly beats the shit out of them. Later, Harry learns from Swan about a deranged fan named Harlan Rook, who accused Swan of stealing his screenplay over a year ago and has been stalking him ever since. It now appears that Rook has taken on Swan’s persona and is suffering from “process schizophrenia.” Rook builds a high-powered remote-control toy car and arms it with C-4 explosive. From his vantage point in a car a couple blocks away, Rook pilots his R/C car under the automobile of a local talk show host, detonating it just as the man is about to drive off to a tennis game. Harry and Quan visit the crime scene and Harry discovers a wheel from the R/C car among the burned wreckage, puzzled as to why it would be there.

Soon enough, Harry discovers what the wheel means. While he and Quan are driving through the city, they see a toy R/C car approach their vehicle. Harry realizes that the car is a bomb meant for him and speeds off, leading to the best sequence in the film, and one of the more creative chase scenes in recent movie memory. Harry and Quan race through San Francisco with the R/C car hot on their trail, and Rook also chasing them while piloting the explosive toy car. The scene is something of a parody of the big car chase scene in Bullitt with Steve McQueen, and it was one of the elements that actually attracted Eastwood to the script in the first place. Trapped in an alleyway with Rook at the other end and his deadly R/C car approaching them, Harry manages to steer his car so that the engine takes the brunt of the explosion. He escapes unscathed, but true to franchise form, his partner Quan ends up in the hospital and out of commission.

Hicks is my new pen pal. I’m going to be sending him a letter once a week telling him how I’m looking in on his sick mother, and how I’m trying to get him special privileges here at the prison. If anything happens to me and Hicks doesn’t get his letter, he’s gonna be really pissed off. He’s gonna come down here and see you because you’re the mailman. In fact, he’ll probably cancel your ass like a stamp. So, you better insure prompt courteous deliver and pray nothing happens to me.
Harry

Rook, pretending to be Swan, calls Samantha and offers to give her an exclusive interview about the dead pool. Eager for the story, she bites, but soon finds herself tied up in a warehouse at the pier where Swan has been shooting his movie. Harry and other cops raid Rook’s apartment, which is a shrine of sorts to Swan’s career, and Harry discovers a dead pool list with Samantha’s name on it. He learns from the TV station that she was going to meet Swan and follows the trail to the docks. Rook threatens to cut Samantha’s throat unless Harry gives up his gun, which he does. Samantha breaks free and she and Harry make a run for it, with a crazed Rook chasing after them, shooting off Harry’s gun with abandon. The chases leads to the pier, where Rook loses Harry and Samantha. He calls out for Harry to show himself, then hears Harry call out from the shadows, “You’re out of bullets.” Harry emerges holding the harpoon gun fired by Slash earlier in the film, by far the largest gun that Dirty Harry has ever carried. He shoots Rook with it, impaling him to a wall. Evil is punished, justice is served, and Harry and Samantha walk off together, ignoring the crowd of reporters who have gathered to get the exclusive.

At 91 minutes, The Dead Pool was the shortest film in the Dirty Harry series, which is a shame. Even just an extra ten minutes to flesh out the story might have avoided some of the problematic elements of the script, like the embarrassingly contrived way in which Harry and Quan learn about the dead pool at the end of the first act and how Rook’s character is introduced. As the true villain of the story, he is sprung on us so late in the film that it almost makes it seem as if we are watching two different movies—the first a mystery thriller, and the second a two-dimensional action picture. Due in part to these script problems, The Dead Pool was also the least profitable film in the series, earning just $38 million off a $31 million budget. Not quite the financial cushion that Eastwood envisioned to soften the impending commercial failure of Bird. Released during the summer movie season rather than the traditional end-of-the-year slot that the other Dirty Harry films enjoyed and dominated, The Dead Pool faced stiff competition at the box office from Big, Who Framed Roger Rabbit, and Die Hard, a film with some recognizable Dirty Harry elements that would set the template for big budget action films for the next decade.

Another reason that The Dead Pool didn’t resonate with fans was that movie audiences were growing away from Dirty Harry. The films that Eastwood’s classic character inspired had grown to become more popular than their inspirational source; the son grows up and becomes his own man, and the father must step aside. It’s evolution, and it’s inevitable. Eastwood was 58 in 1988, and he knew then, regardless of how The Dead Pool was received at the box office, that this was going to be his last go-round as Dirty Harry. To continue would be to invite parody, and any future endeavors would sully the great work that had come before. In The Dead Pool, we see Harry mixed up in another adventure that does not advance the character’s narrative nor add to the conversation about the criminal justice system that had been so keenly and smartly explored in the previous four films. Drumming up just another adventure was something that Eastwood swore he would never do with Dirty Harry. Unfortunately, that is exactly what happened here.

Despite The Dead Pool being the weakest entry in the franchise, Dirty Harry’s status as a classic American film character is solid. Adjusting for inflation, the Dirty Harry movies pulled in close to a billion dollars at the box office, to say nothing about home video sales and rentals and television airings, all of which were quite robust throughout the 80s and 90s. Even more important than the dollars, at least to anyone outside Hollywood, is that Dirty Harry became an American icon, a symbol of a time and a sensibility that made people reflect on the world they lived in. The character stirred a shit storm with critics and audiences not once but four times, with each film drawing a bigger audience than its predecessor up through and including Sudden Impact. And four out of five ain’t bad. Most filmmakers would be lucky to have one in a hundred. And we are lucky punks to have had a hero like Dirty Harry to cheer for and give voice to our frustrations with a world where justice seems scarce. We lived vicariously through Harry Callahan, and he made us feel good about the world. And that’s why we go to the movies in the first place.