Eastwood directed two films about World War II's Battle of Iwo Jima released In 2006. The first, Flags of Our Fathers, focused on the men who raised the American flag on top of Mount Suribachi and featured the film debut of Eastwood's son Scott. This was followed by Letters from Iwo Jima, which dealt with the tactics of the Japanese soldiers on the island and the letters they wrote home to family members. Letters from Iwo Jima was the first American film to depict a war issue completely from the view of an American enemy. Both films received praise from critics and garnered several nominations at the 79th Academy Awards, including Best Director, Best Picture, and Best Original Screenplay for Letters from Iwo Jima. At the 64th Golden Globe Awards Eastwood received nominations for Best Director in both films. Letters from Iwo Jima won the award for Best Foreign Language Film.
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 directed and starred in True Crime (1999). He plays Steve Everett, a journalist and recovering alcoholic, who has to cover the execution of murderer Frank Beechum (played by Isaiah Washington). True Crime received a mixed reception, with Janet Maslin of The New York Times writing, "his direction is galvanized by a sense of second chances and tragic misunderstandings, and by contrasting a larger sense of justice with the peculiar minutiae of crime. Perhaps he goes a shade too far in the latter direction, though." The film was a box office failure, earning less than half its $55 million budget and was Eastwood's worst-performing film of the 1990s aside from White Hunter Black Heart, which had a limited release.More Info
At the May 1994 Cannes Film Festival Eastwood received France's Ordre des Arts et des Lettres medal, and on March 27, 1995, he was awarded the Irving G. Thalberg Memorial Award at the 67th Academy Awards. His next film appearance was in a cameo role as himself in the children's film Casper (1995). He expanded his repertoire by playing opposite Meryl Streep in The Bridges of Madison County (also 1995). Based on the novel by Robert James Waller, the film relates the story of Robert Kincaid (Eastwood), a photographer working for National Geographic who, while photographing historic covered bridges in Iowa, meets and has an affair with an Italian-born farm wife, Francesca (Streep). Despite the novel receiving unfavorable reviews, The Bridges of Madison County film was a commercial and critical success. Roger Ebert wrote, "Streep and Eastwood weave a spell, and it is based on that particular knowledge of love and self that comes with middle age." The film was nominated for a Golden Globe for Best Picture and won a César Award in France for Best Foreign Film. Streep was also nominated for an Academy Award and a Golden Globe.More Info
Eastwood played Frank Horrigan in the Secret Service thriller In the Line of Fire (1993), directed by Wolfgang Petersen and co-starring John Malkovich and Rene Russo. Horrigan is a guilt-ridden Secret Service agent haunted by his failure to save John F. Kennedy's life. The film was among the top 10 box office performers in that year, earning $102 million in the United States alone, and 25 years after he was first listed on Quigley's Top Ten Money Making Stars Poll, Eastwood was voted number one again. A few months after film wrapped, Eastwood directed and co-starred alongside Kevin Costner in A Perfect World (also 1993). Set in the 1960s, Eastwood plays a Texas Ranger in pursuit of an escaped convict (Costner) who hits the road with a young boy (T.J. Lowther). Janet Maslin of The New York Times wrote that the film marked the highest point of Eastwood's directing career, and the film has since been cited as one of his most underrated directorial achievements.More Info
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