SFPD Inspector Harry Callahan's testimony against crime kingpin Lou Janero puts the mobster in prison. Callahan becomes famous and the target of Janero's men, both of which he dislikes. After Callahan kills four attackers during an ambush, the department assigns Al Quan (Evan Kim) as his partner; Callahan advises him to get a bulletproof vest as his partners often get killed. They investigate the death of rock singer Johnny Squares (Jim Carrey), found in his trailer during filming of a slasher film directed by Peter Swan (Liam Neeson) at the Port of San Francisco.
Dean Madison, Swan's executive producer, is killed during a Chinatown restaurant robbery. Callahan kills four of the robbers, and Quan captures the fifth. They discover a list in Madison's pocket with Callahan and Squares's names on it, and learn that Madison and Swan are participants in a "dead pool" game, in which participants predict celebrity deaths in the Bay area, whether by accident, violence, or natural causes. Another on Swan's list, movie critic Molly Fisher, is killed by an intruder claiming to be Swan, causing panic among the surviving celebrities and making Swan a suspect.
After Callahan destroys a television station's camera filming Squares's girlfriend, to avoid a lawsuit he must cooperate with reporter Samantha Walker (Patricia Clarkson). She offers to drop the lawsuit if the famous detective agrees to a profile of his controversial career, but Callahan accuses her of wanting to exploit the danger he is in for ratings. They survive another attack by Janero's men; the incident, and her own unwillingness to be the subject of news coverage, cause the reporter to reconsider the dangers police officers face versus the public's right to know.
At San Quentin State Prison, where Janero is serving his sentence, Callahan uses triple murderer Butcher Hicks to threaten Janero if anything happens to him. Janero ends the attacks, and assigns two men to Callahan as his personal bodyguards.
Gus Wheeler, claiming responsibility for the murders, douses himself in gasoline and threatens to immolate himself. He is not the murderer, but an attention seeker desperate to appear on camera. Walker foils Wheeler's plan by refusing to film him; Wheeler accidentally sets himself on fire, but Callahan saves him. Impressed by her refusal to exploit Wheeler, Callahan and Walker become close.
Swan tells Callahan and Quan of Harlan Rook, a schizophrenic and deranged fan who thinks the director stole his ideas and work; Swan has a restraining order against him. Rook kills talk show host Nolan Kennard, another person on the dead pool list, using a radio-controlled car filled with C4 explosive under the victim's vehicle. Callahan finds a toy car wheel at the crime scene, and later sees another toy car following him and Quan. Recognizing the threat, they flee through the city pursued by the car and Rook himself. The detectives are trapped in an alleyway, but their car's engine takes most of the blast; Quan survives with only broken ribs, thanks to his bulletproof vest.
Rook, claiming to be Swan, calls Walker at the television station and invites her to Swan's film studio for an interview. The police discover at Rook's apartment torn posters of Swan's films, large quantities of explosives, and Walker's name replacing Callahan's on the dead pool list. At the studio, Callahan confronts Rook holding Walker hostage. The detective surrenders his .44 Magnum revolver after Rook threatens to slit her throat. Callahan lures Rook to a pier after a chase during which Rook shoots at him with his own gun. Rook runs out of ammunition, and Callahan shoots Rook with a Svend Foyn harpoon cannon, impaling him. Callahan leaves with Walker as the police arrive.Clint Eastwood as Inspector Harry CallahanPatricia Clarkson as Samantha WalkerLiam Neeson as Peter SwanEvan C. Kim as Inspector Al QuanDavid Hunt as Harlan RookMichael Currie as Captain DonnellyMichael Goodwin as Lt. AckermanJim Carrey as Johnny SquaresAnthony Charnota as Lou JaneroRonnie Claire Edwards as Molly FisherLouis Giambalvo as Gus WheelerDiego Chairs as Butcher HicksCharles Martinet as Police Station ReporterPatrick Van Horn as Freeway ReporterShawn Elliott as Chester DockstederBill Wattenburg as Nolan KennardMarc Alaimo as BodyguardJustin Whalin as JasonHarry Demopoulos as Doctor in Hospital
The Dead Pool is the only Dirty Harry film in which Albert Popwell does not appear. He was not available due to a scheduling conflict with filming on Who's That Girl.
Members of the hard rock band Guns N' Roses make uncredited cameo appearances at the funeral of Johnny Squares. They also appear during filming of a "nightmare scene" at the docks, where guitarist Slash fires a harpoon gun through a window and is berated by Swan.
Eastwood reacted to starring in another Dirty Harry film, "It's fun, once in a while, to have a character you can go back to. It's like revisiting an old friend you haven't seen for a long time. You figure 'I'll go back and see how he feels about things now.'" The Dead Pool was filmed between February and March 1988 in San Francisco.
Callahan is pursued through San Francisco's hilly streets in his unmarked Oldsmobile 98 squad car by a remote-controlled bomb assembled by Rook, disguised as a radio-controlled car. The "bomb" was in fact a highly modified Associated RC10 electric race buggy powered by Reedy motor that had to be geared up high to a 8.4v NiCd battery topped with an off-the-shelf 1963 Chevrolet Corvette body by Parma International. The car had its suspension lowered from the original for a lower ground clearance. Needing the best driver to carry out the stunt, Van Horn chose the 1985 off-road world champion radio control driver Jay Halsey. At first, Van Horn was unsure if the R/C car could keep up with the Oldsmobile so for the scene where they started from the top of the hill, the director allowed the two cars to start together, as a result, the former led the latter therefore the shot had to reshot with Eastwood reaching the bottom first. At one take in a scene where the cars jumped, the RC10 jumped over the Oldsmobile and waited for it at the end of the street. Halsey was only required to drive his car at full speed at a scene where the bomb was about to be detonated. These scene took a week and a half to film and a motorized tricycle with a camera mounted at ground level was used to film the RC10. The sound effects of the "engine" were added in post production. This chase scene has many similarities with the famous chase in the Steve McQueen film Bullitt. Eastwood has said that the chase was his favorite part of the film. The necessity of closing down various continuously busy city streets meant that the sequences tend to jump about from district to district, much as the similar scenes did in the McQueen film, making for a number of continuity errors that are easily overlooked during the fast-paced scenes, much as the motorcycle chase scenes in the second Harry film jumped around but are seldom mentioned.
The Dead Pool received mixed reviews. It holds a 52% approval rating on the review aggregate website Rotten Tomatoes. Roger Ebert of the Chicago Sun-Times gave the film a thumbs up and said "As good as the original. Smart, quick and made with real wit." Gene Siskel of the Chicago Tribune also gave it a thumbs up and said "Perhaps the best Dirty Harry film since the original." Many consider it to be the worst of the Dirty Harry movies.
The Dead Pool was released in United States theaters in July 1988. In its opening weekend, the film took $9,071,330 in 1,988 theaters in the US, at an average of $4,954. In total in the US, the film made $37,903,295, making it almost the least profitable of the five films in the Dirty Harry franchise.
The song "Welcome to the Jungle" by Guns N' Roses appears as the theme song for Swan's movie, as used in a scene during filming where Johnny Squares is lip-synching. The band can be seen as extras during the funeral scene. The traditional Dirty Harry End Theme (Variously called "Harry's Theme", "Sad Theme" and with lyrics "This Side of Forever") is given a full Hollywood Big Band treatment, lasting longer than any other film version of the song, perhaps as a coda to the entire series.
Eastwood has publicly announced that he has no interest in acting in another Dirty Harry film. In 2000, he jokingly spoke about potential sequels: "Dirty Harry VI! Harry is retired. He's standing in a stream, fly-fishing. He gets tired of using the pole— and BA-BOOM! Or Harry is retired, and he catches bad guys with his walker?"