Eastwood starred in The Dead Pool (1988), the fifth and final film in the Dirty Harry series. It co-starred Patricia Clarkson, Liam Neeson, and a young Jim Carrey who plays Johnny Squares, a drug-addled rock star and the first of the victims on a list of celebrities drawn up by horror film director Peter Swan (Neeson) who are deemed most likely to die, the so-called "Dead Pool". The list is stolen by an obsessed fan who, in mimicking his favorite director, makes his way through the list killing off celebrities, of which Dirty Harry is also included. The Dead Pool grossed nearly $38 million, relatively low receipts for a Dirty Harry film. It is generally viewed as the weakest film of the series, though Roger Ebert thought it was as good as the original.
Before Hang 'Em High's release, Eastwood had already begun working on Coogan's Bluff (1968), about an Arizona deputy sheriff tracking a wanted psychopathic criminal (Don Stroud) through New York City. He was reunited with Universal Studios for it after receiving an offer of $1 million – more than double his previous salary. Jennings Lang arranged for Eastwood to meet Don Siegel, a Universal contract director who later became Eastwood's close friend, forming a partnership that would last more than ten years and produce five films. Shooting began in November 1967, before the script had been finalized. The film was controversial for its portrayal of violence. Coogan's Bluff also became the first collaboration with Argentine composer Lalo Schifrin, who scored several Eastwood films in the 1970s and 1980s, including the Dirty Harry films.
More InfoEastwood was then offered the role of Benjamin L. Willard in Francis Coppola's Apocalypse Now, but declined as he did not want to spend weeks on location in the Philippines. He also refused the part of a platoon leader in Ted Post's Vietnam War film, Go Tell the Spartans and instead decided to make a third Dirty Harry film, The Enforcer (1976). The film had Callahan partnered with a new female officer (Tyne Daly) to face a San Francisco Bay area group resembling the Symbionese Liberation Army. The film, culminating in a shootout on Alcatraz island, was considerably shorter than the previous Dirty Harry films at 95 minutes, but was a major commercial success grossing $100 million worldwide to become Eastwood's highest-grossing film to date.
More InfoEastwood was then offered the role of Benjamin L. Willard in Francis Coppola's Apocalypse Now, but declined as he did not want to spend weeks on location in the Philippines. He also refused the part of a platoon leader in Ted Post's Vietnam War film, Go Tell the Spartans and instead decided to make a third Dirty Harry film, The Enforcer (1976). The film had Callahan partnered with a new female officer (Tyne Daly) to face a San Francisco Bay area group resembling the Symbionese Liberation Army. The film, culminating in a shootout on Alcatraz island, was considerably shorter than the previous Dirty Harry films at 95 minutes, but was a major commercial success grossing $100 million worldwide to become Eastwood's highest-grossing film to date.
More InfoStardom brought Eastwood more roles. He signed to star in the American revisionist western Hang 'Em High (1968) alongside Inger Stevens, Pat Hingle, Dennis Hopper, Ed Begley, Alan Hale, Jr., Ben Johnson, Bruce Dern, and James MacArthur, playing a man who takes up a Marshal's badge and seeks revenge as a lawman after being lynched by vigilantes and left for dead. The film earned Eastwood $400,000 and 25% of its net box office. Using money earned from the Dollars trilogy, Eastwood's advisor Irving Leonard helped establish Eastwood's own production company, Malpaso Productions, named after Malpaso Creek on Eastwood's property in Monterey County, California. The 38-year-old actor was still relatively unknown as late as a month prior to the film's release, as evidenced by a July 1968 news item by syndicated columnist Dorothy Manners: "The proverbial man in the street is still asking, 'Who's Clint Eastwood?'" Leonard arranged for Hang 'Em High to be a joint production with United Artists; when it opened in August 1968, it had the largest opening weekend in United Artists' history. Hang 'Em High was widely praised by critics, including Archer Winsten of the New York Post, who called it "a western of quality, courage, danger and excitement."
More InfoEastwood directed and starred in The Gauntlet (1977) opposite Locke, Pat Hingle, William Prince, Bill McKinney, and Mara Corday. In this film, he portrays a down-and-out cop assigned to escort a prostitute from Las Vegas to Phoenix to testify against the mob. Although a moderate hit with the viewing public, critics had mixed feelings about the film, with many believing it was overly violent. Ebert, in contrast, gave the film three stars and called it "classic Clint Eastwood: fast, furious, and funny." In Every Which Way but Loose (1978) he has an uncharacteristic offbeat comedy role. His character, Philo Beddoe, is a trucker and brawler who roams the American West searching for a lost love (Locke) accompanied by his best friend, Orville Boggs (played by Geoffrey Lewis) and an orangutan called Clyde. The film proved surprisingly successful upon its release and became Eastwood's most commercially successful film up to that time. Panned by critics, it ranked high among the box-office successes of his career and was the second-highest-grossing film of 1978.
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