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1990–2009: critical acclaim and awards success

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.

f possible, he looks even taller, leaner and more mysteriously possessed than he did in Sergio Leone's seminal Fistful of Dollars a quarter of a century ago. The years haven't softened him. They have given him the presence of some fierce force of nature, which may be why the landscapes of the mythic, late 19th-century West become him, never more so than in his new Unforgiven.... This is his richest, most satisfying performance since the underrated, politically lunatic Heartbreak Ridge. There's no one like him.

Eastwood revisited the western genre in Unforgiven (1992), a film which he directed and starred in as an aging ex- gunfighter long past his prime. Scripts existed for the film as early as 1976 under titles such as The Cut-Whore Killings and The William Munny Killings, but Eastwood delayed the project because he wanted to wait until he was old enough to play his character and to savor it as the last of his western films. Unforgiven was a major commercial and critical success; Jack Methews of the Los Angeles Times described it as "the finest classical western to come along since perhaps John Ford's 1956 The Searchers ". The film was nominated for nine Academy Awards (including Best Actor for Eastwood and Best Original Screenplay for David Webb Peoples), and won four, including Best Picture and Best Director for Eastwood. In June 2008 Unforgiven was ranked as the fourth-best American western, behind Shane, High Noon, and The Searchers in the American Film Institute 's " AFI's 10 Top 10 " list.

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.

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.

Eastwood directed and starred in the political thriller Absolute Power (1997), alongside Gene Hackman (with whom he had appeared in Unforgiven). Eastwood played the role of a veteran thief who witnesses the Secret Service cover-up of a murder. The film received a mixed reception from critics. Later in 1997, Eastwood directed Midnight in the Garden of Good and Evil, based on the novel by John Berendt and starring John Cusack, Kevin Spacey, and Jude Law. The film met with a mixed critical response.

The roles that Eastwood has played, and the films that he has directed, cannot be disentangled from the nature of the American culture of the last quarter century, its fantasies and its realities.

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.

Eastwood directed and starred in Space Cowboys (2000) alongside Tommy Lee Jones, Donald Sutherland and James Garner. Eastwood played one of a group of veteran ex-test pilots sent into space to repair an old Soviet satellite. The original music score was composed by Eastwood and Lennie Niehaus. Space Cowboys was critically well-received and holds a 79 percent rating at Rotten Tomatoes, although Roger Ebert wrote that the film was, "too secure within its traditional story structure to make much seem at risk". The film grossed more than $90 million in its United States release, more than Eastwood's two previous films combined. Eastwood played an ex- FBI agent chasing a sadistic killer (Jeff Daniels) in the thriller Blood Work (2002), loosely based on the 1998 novel of the same name by Michael Connelly. The film was a commercial failure, grossing just $26.2 million on an estimated budget of $50 million and received mixed reviews, with Rotten Tomatoes describing it as, "well-made but marred by lethargic pacing".

Eastwood directed and scored the crime drama Mystic River (2003), a film dealing with themes of murder, vigilantism and sexual abuse and starring Sean Penn, Kevin Bacon, and Tim Robbins. The film was praised by critics and won two Academy Awards – Best Actor for Penn and Best Supporting Actor for Robbins – with Eastwood garnering nominations for Best Director and Best Picture. The film grossed $90 million domestically on a budget of $30 million. In 2003, Eastwood was named Best Director of the Year by the National Society of Film Critics.

Clint is a true artist in every respect. Despite his years of being at the top of his game and the legendary movies he has made, he always made us feel comfortable and valued on the set, treating us as equals.

The following year, Eastwood found further critical acclaim with Million Dollar Baby. The boxing drama won four Academy Awards for Best Picture, Best Director, Best Actress (Hilary Swank) and Best Supporting Actor (Morgan Freeman). At age 74, Eastwood became the oldest of eighteen directors to have directed two or more Best Picture winners. He also received a nomination for Best Actor, as well as a Grammy nomination for his score, and won a Golden Globe for Best Director, which was presented to him by daughter Kathryn, who was Miss Golden Globe at the 2005 ceremony. A. O. Scott of The New York Times lauded the film as a "masterpiece" and the best film of the year.

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 next directed Changeling (2008), based on a true story set in the late 1920s. Angelina Jolie stars as a woman reunited with her missing son only to realize he is an impostor. After its release at several film festivals the film grossed over $110 million, the majority of which came from foreign markets. The film was highly acclaimed, with Damon Wise of Empire describing Changeling as "flawless". Todd McCarthy of Variety magazine described it as "emotionally powerful and stylistically sure-handed" and that the film's characters and social commentary were brought into the story with an "almost breathtaking deliberation". For the film, Eastwood received nominations for Best Original Score at the 66th Golden Globe Awards, Best Direction at the 62nd British Academy Film Awards and director of the year from the London Film Critics' Circle.

Eastwood ended a four-year "self-imposed acting hiatus" by appearing in Gran Torino (also 2008), which he also directed, produced and partly scored with his son Kyle and Jamie Cullum. Biographer Marc Eliot called Eastwood's role "an amalgam of the Man with No Name, Dirty Harry, and William Munny, here aged and cynical but willing and able to fight on whenever the need arose". Gran Torino grossed almost $30 million during its opening weekend release in January 2009, the highest of his career as an actor or director. Gran Torino eventually grossed over $268 million in theaters worldwide, becoming the highest-grossing film of Eastwood's career so far (without adjustment for inflation).

Eastwood's 30th directorial outing came with Invictus (2009), a film based on the story of the South African team at the 1995 Rugby World Cup with Morgan Freeman as Nelson Mandela, Matt Damon as rugby team captain François Pienaar, and Grant L. Roberts as Ruben Kruger. The film was met with generally positive reviews; Roger Ebert gave it three and a half stars and described it as a "very good film... with moments evoking great emotion", while Variety ' s Todd McCarthy wrote, "Inspirational on the face of it, Clint Eastwood's film has a predictable trajectory, but every scene brims with surprising details that accumulate into a rich fabric of history, cultural impressions and emotion." For the film, Eastwood was nominated for Best Director at the 67th Golden Globe Awards.