Also in 1971, Eastwood moved behind the camera, making his directorial debut with the thriller Play Misty for Me, the first offering from his production company, Malpaso. Over the next two decades, he turned in solid performances in films such as The Outlaw Josey Wales (1976), Every Which Way But Loose (1978), Escape From Alcatraz (1979) and Honkytonk Man (1982), but seemed to be losing his star power for lack of a truly great film. By the end of the 1980s, after four Dirty Harry sequels, released from 1973 to 1988, Eastwood was poised to escape the character’s shadow and emerge as one of Hollywood’s most successful actor-turned-directors. In 1992, he hit the jackpot when he starred in, directed and produced the darkly unconventional Western Unforgiven. The film won four Oscars, including Best Supporting Actor (Gene Hackman), Best Film Editing, Best Director and Best Picture, both for Eastwood. He also found box-office success as a late-in-life action and romantic hero, in In the Line of Fire (1993) and The Bridges of Madison County (1995), respectively.
As a director, Eastwood worked steadily over the next decade, making such films as Midnight in the Garden of Good and Evil (1997), Absolute Power (1997) and, most notably, the crime drama Mystic River (2003), for which he was again nominated for the Best Director Oscar. The following year, he hit a grand slam with Million Dollar Baby, in which he also starred as the curmudgeonly coach of a determined young female boxer (Hilary Swank, in her second Oscar-winning performance). In addition to Swank’s Academy Award for Best Actress, the film won Oscars for Best Supporting Actor (Morgan Freeman) and Eastwood’s second set of statuettes for Best Director and Best Picture.
In 2006, Eastwood became only the 31st filmmaker in 70 years to receive a Lifetime Achievement Award from the Directors Guild of America (DGA). That year, he directed a pair of World War II themed movies, Flags of Our Fathers (2006) and Letters from Iwo Jima (2006). The latter film, which featured an almost exclusively Japanese cast, earned an Oscar nomination for Best Picture and a fourth Best Director nomination for Eastwood (his 10th nomination overall). Off-screen, Eastwood has pursued an interest in politics, serving as mayor of Carmel, California, from 1986 to 1988. He was married to Maggie Johnson in 1953, and the couple had two children, Kyle and Alison (who co-starred in Midnight in the Garden of Good and Evil), before separating in 1978 and divorcing in 1984. Eastwood also had long-term relationships with the actresses Sondra Locke and Frances Fisher (with whom he had a daughter, Francesca). He married his second wife, Dina Ruiz Eastwood, in 1996. Their daughter, Morgan, was born that same year.