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's first western as director was High Plains Drifter (1973), in which he also starred. The film had a moral and supernatural theme, later emulated in Pale Rider. The plot follows a mysterious stranger (Eastwood) who arrives in a brooding Western town where the people hire him to protect them against three soon-to-be-released felons. There remains confusion during the film as to whether the stranger is the brother of the deputy, whom the felons lynched and murdered, or his ghost. Holes in the plot were filled with black humor and allegory, influenced by Leone. The revisionist film received a mixed reception, but was a major box-office success. A number of critics thought Eastwood's directing was "as derivative as it was expressive," with Arthur Knight of the Saturday Review remarking that Eastwood had "absorbed the approaches of Siegel and Leone and fused them with his own paranoid vision of society." John Wayne, who had declined a role in the film, sent a letter to Eastwood soon after the film's release in which he complained that, "The townspeople did not represent the true spirit of the American pioneer, the spirit that made America great."
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 began working on smaller, more personal projects and experienced a lull in his career between 1988 and 1992. Always interested in jazz, he directed Bird (1988), a biopic starring Forest Whitaker as jazz musician Charlie "Bird" Parker. Alto saxophonist Jackie McLean and Spike Lee, son of jazz bassist Bill Lee and a long time critic of Eastwood, criticized the characterization of Charlie Parker remarking that it did not capture his true essence and sense of humor. Eastwood received two Golden Globes for the film, the Cecil B. DeMille Award for his lifelong contribution, and the Best Director award. However, Bird was a commercial failure, earning just $11 million, which Eastwood attributed to the declining interest in jazz among black people. Carrey would appear with Eastwood again in the poorly-received comedy Pink Cadillac (1989). The film is about a bounty hunter and a group of white supremacists chasing an innocent woman (Bernadette Peters) who tries to outrun everyone in her husband's prized pink Cadillac. The film failed both critically and commercially, earning barely more than Bird and marking a low point in Eastwood's career.
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.
More InfoBefore 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.
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