Eastwood 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.
Eastwood directed and played the title role in Bronco Billy (1980), alongside Locke, Scatman Crothers, and Sam Bottoms. Eastwood has cited Bronco Billy as being one of the most relaxed shoots of his career and biographer Richard Schickel argued that Bronco Billy is Eastwood's most self-referential character. The film was a commercial disappointment, but was liked by critics. Janet Maslin of The New York Times wrote that film was "the best and funniest Clint Eastwood movie in quite a while", and praised Eastwood's directing, intricately juxtaposing the old West and the new West. Released later in 1980, Any Which Way You Can, was the sequel to Every Which Way but Loose and also starring Eastwood. The film received a number of bad reviews from critics, although Maslin described it as "funnier and even better than its predecessor". In theaters over the Christmas season, Any Which Way You Can was a major box office success and ranked among the top five highest-grossing films of the year.More Info
Eastwood 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 Info
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 Info
Eastwood teamed up with Jeff Bridges and George Kennedy in the buddy action caper Thunderbolt and Lightfoot (1974), a road movie about a veteran bank robber Thunderbolt (Eastwood) and a young con man drifter, Lightfoot (Bridges). On its release, in spring 1974, the film was praised for its offbeat comedy mixed with high suspense and tragedy but was only a modest success at the box office, earning $32.4 million. Eastwood's acting was noted by critics, but was overshadowed by Bridges who was nominated for an Academy Award for Best Supporting Actor. Eastwood reportedly fumed at the lack of Academy Award recognition for him and swore that he would never work for United Artists again.More Info
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