Bird (1988) Eastwood, a jazz aficionado, takes on the life story of Charlie 'Bird' Parker (Forest Whitaker), who was haunted by drugs and alcohol. This biopic follows the ups and downs of the troubled saxophonist's life, from his childhood in Kansas City in the 1940s through his days in New York until his death at the age of 34. The moody film, accompanied by a fabulous soundtrack, showcased Eastwood's mature and delicate direction. The Bridges of Madison County (1995) Eastwood directs, produces and casts himself (against type) as a lonely photographer who meets and falls in love with a housewife (Meryl Streep) in this poignant middle-aged romance based on Robert James Wallers' best-selling novel. Working outside his usual range, Eastwood transcends the potentially sappy tearjerker and turns it into a nuanced, intelligent and genuinely touching, ill-fated love story that lingers in the mind. Unforgiven (1992) Dedicated to mentors Sergio Leone and Don Siegel, this Western, set in a small town run by a corrupt sheriff (Gene Hackman), portrays the old West in a state of decline. A world-weary gunslinger-turned-hog farmer (Eastwood), who has given up violence to raise his two children, is asked to take on one last job by his former partner - and face old demons along the way. Eastwood's dark and depressing take on the genre that catapulted him to fame 30 years ago is a powerful meditation on the West and its myths. The film won four Oscars in 1992, including best picture, best director and best supporting actor (Hackman). Mystic River (2003) Eastwood returns to form after the unimpressive Blood Work (2002) and Space Cowboys (2000) with this complex thriller that blends whodunit with a poignant exploration of the relationship between the protagonists. Adapted from Dennis Lehane's best-selling novel, the film digs deep into the psychological turmoil of three estranged childhood friends who are reunited by a murder mystery 30 years after a tragic incident. A darling with the critics, and Sean Penn and Tim Robbins won Oscars for their performances. Million Dollar Baby (2004) Released in late 2004, this film was an immediate hit with the critics and went on to sweep the Oscars in major categories (best director, best picture, best actor and best actress). It's another pessimistic drama from Eastwood: a headstrong woman from the wrong side of the tracks (Hilary Swank) takes up professional boxing as a ticket to a better life and fights her way to the top under the tutelage of a hard-edged trainer (Eastwood) and his friend (Morgan Freeman). Rather than treating the story as a female Rocky, Eastwood brought a dignity and depth to the cliched genre by raising questions about life and death.