Eastwood has had numerous casual and serious relationships of varying length and intensity over his life, many of which overlapped. Shortly after he met future wife Maggie Johnson on a blind date in spring 1953, Eastwood had a relationship that resulted in a daughter, Laurie (born 1954), who was adopted by Clyde and Helen Warren of Seattle. Although the identity of Laurie's biological mother is not publicly known, biographer Patrick McGilligan said she belonged to a theatre group Eastwood participated in. Eastwood continued having affairs while married to Johnson, including a 1959 to 1973 liaison with stuntwoman Roxanne Tunis that produced a daughter, Kimber (born 1964).
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 InfoAt 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 InfoEastwood next directed Jersey Boys (2014), a musical biography based on the Tony Award-winning Broadway musical. The film told the story of the musical group The Four Seasons. Eastwood directed American Sniper (also 2014), a film adaptation of Chris Kyle's eponymous memoir, following Steven Spielberg's departure from the project. The film was released on December 25, 2014. American Sniper grossed more than $350 million domestically and over $547 million globally, making it one of Eastwood's biggest movies commercially. His next film, Sully, starred Tom Hanks as Chesley Sullenberger, who successfully landed the US Airways Flight 1549 on the Hudson River in an emergency landing, keeping all passengers on board alive. Released in the United States in September 2016, it became another commercial success for Eastwood, grossing over $238 million worldwide. He directed the biographical thriller The 15:17 to Paris (2018), which saw previously non-professional actors Spencer Stone, Anthony Sadler and Alek Skarlatos playing themselves as they stop the 2015 Thalys train attack. The film received a generally negative reception from critics, who were largely critical of the acting by the three leads. Eastwood next starred in and directed The Mule, which was released in December 2018. He played Earl Stone, an elderly drug smuggler based on Leo Sharp, Eastwood's first acting role since Trouble with the Curve in 2012.
More InfoEastwood 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 InfoOn May 24, 2019, it was announced that Eastwood's next film would be titled The Ballad of Richard Jewell, based on the life of heroic security guard Richard Jewell, who was wrongly suspected in the 1996 Olympic bombing. Later retitled simply Richard Jewell, Eastwood directed and produced the film, through Warner Bros., his tenth straight film with the company. Jonah Hill and Leonardo DiCaprio were originally set to star in the film, ultimately serving only as producers. The film stars Paul Walter Hauser in the titular role, along with Sam Rockwell, Kathy Bates, Jon Hamm, and Olivia Wilde in supporting roles. Filming began on June 24, 2019, and Richard Jewell was released on December 13, 2019.
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