In 1992 Eastwood surprised everyone by earning himself an Oscar for best director and producer of the best picture and nominated for best actor. Then he took on the secret service in In the Line of Fire (1993), another huge hit. Next up was The Bridges of Madison County (1995), a popular love story with Meryl Streep. Over the next few years, the quality of his films was up and down. He directed and starred in the well-received Absolute Power (1997) and Space Cowboys (2000), and the badly received True Crime (1999) and Blood Work (2002).
However, Eastwood rose to prominence once again, starring opposite Hilary Swank and Morgan Freeman in what is arguably the best film of his career: the boxing drama Million Dollar Baby (2004). A critical and commercial triumph, the movie won the Academy Award for Best Picture, as well as earning Eastwood a nomination for Best Actor and a win for Best Director. After this he took a four-year acting hiatus before starring in Gran Torino (2008). This film grossed $30 million during its opening weekend in 2009, making him the oldest leading man to reach #1 at the box office, and another one of his biggest hits.
After starring in iconic movies for five consecutive decades, Clint Eastwood has proved himself to be the longest-running movie star. Going out on top, he recently said he will likely never act again, though he will continue to direct films.
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