Eastwood directed and starred in White Hunter Black Heart (1990), an adaptation of Peter Viertel's roman à clef, about John Huston and the making of the classic film The African Queen. Shot on location in Zimbabwe in the summer of 1989, the film received some critical attention but with only a limited release earned just $8.4 million. Eastwood directed and co-starred with Charlie Sheen in The Rookie, a buddy cop action film released in December 1990. Critics found the film's plot and characterization unconvincing, but praised its action sequences. An ongoing lawsuit, in response to Eastwood allegedly ramming a woman's car, resulted in no Eastwood films being shown in cinemas in 1991. Eastwood won the suit and agreed to pay the complainant's legal fees if she did not appeal.
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.
More InfoTightrope (1984) had Eastwood starring opposite Geneviève Bujold in a provocative thriller, inspired by newspaper articles about an elusive Bay Area rapist. Set in New Orleans to avoid confusion with the Dirty Harry films, Eastwood played a divorced cop drawn into his target's tortured psychology and fascination for sadomasochism. Tightrope was a critical and commercial hit and became the fourth highest-grossing R-rated film of 1984. Eastwood next starred in the crime comedy City Heat (also 1984) alongside Burt Reynolds, a film about an ex-cop turned private eye and his former police lieutenant partner who get mixed up with gangsters in the Prohibition era of the 1930s. The film grossed around $50 million domestically, but was overshadowed by Eddie Murphy's Beverly Hills Cop.
More InfoTightrope (1984) had Eastwood starring opposite Geneviève Bujold in a provocative thriller, inspired by newspaper articles about an elusive Bay Area rapist. Set in New Orleans to avoid confusion with the Dirty Harry films, Eastwood played a divorced cop drawn into his target's tortured psychology and fascination for sadomasochism. Tightrope was a critical and commercial hit and became the fourth highest-grossing R-rated film of 1984. Eastwood next starred in the crime comedy City Heat (also 1984) alongside Burt Reynolds, a film about an ex-cop turned private eye and his former police lieutenant partner who get mixed up with gangsters in the Prohibition era of the 1930s. The film grossed around $50 million domestically, but was overshadowed by Eddie Murphy's Beverly Hills Cop.
More InfoEastwood made his only foray into TV direction with the Amazing Stories episode Vanessa in the Garden (1985), which starred Harvey Keitel and Locke as a married couple. This was his first collaboration with Steven Spielberg, who later co-produced Flags of Our Fathers and Letters from Iwo Jima. He would revisit the Western genre when he directed and starred in Pale Rider (1985), a film based on the classic western Shane (1953) and follows a preacher descending from the mists of the Sierras to side with the miners during the California Gold Rush of 1850. The title is a reference to the Four Horsemen of the Apocalypse, as the rider of the pale horse is Death, and shows similarities to Eastwood's western High Plains Drifter (1973) in its themes of morality and justice as well as its exploration of the supernatural. It was hailed as one of the best films of 1985 and the best western to appear for a considerable period, with Gene Siskel of the Chicago Tribune remarking, "This year (1985) will go down in film history as the moment Clint Eastwood finally earned respect as an artist".
More InfoEastwood starred with Shirley MacLaine in the western Two Mules for Sister Sara (1970), directed by Don Siegel. The film follows an American mercenary, who becomes mixed up with a prostitute disguised as a nun, and ends up helping a group of Juarista rebels during the reign of Emperor Maximilian I of Mexico. Eastwood again played a mysterious stranger – unshaven, wearing a serape-like vest, and smoking a cigar. Although it received moderate reviews, the film is listed in The New York Times Guide to the Best 1,000 Movies Ever Made. Around the same time, Eastwood starred as one of a group of Americans who steal a fortune in gold from the Nazis, in the World War II film Kelly's Heroes (also 1970), with Donald Sutherland and Telly Savalas. Kelly's Heroes was the last film Eastwood appeared in that was not produced by his own Malpaso Productions. Filming commenced in July 1969 on location in Yugoslavia and in London. The film received mostly a positive reception and its anti-war sentiments were recognized. In the winter of 1969–70, Eastwood and Siegel began planning his next film, The Beguiled (1971), a tale of a wounded Union soldier, held captive by the sexually repressed matron (played by Geraldine Page) of a Southern girls' school. Upon release the film received major recognition in France and is considered one of Eastwood's finest works by French critics. However, it grossed less than $1 million and, according to Eastwood and Lang, flopped due to poor publicity and the "emasculated" role of Eastwood.
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