Eastwood was connecting to something changing in the world and himself. He wasn’t a baby boomer, but many of his fans were, and they were stirred by his fall musings. With era-defining musicians like Neil Young (“Harvest Moon”), Paul Simon (“The Rhythm of the Saints”) and Don Henley (“The End of the Innocence”) leaning into the melancholy of age medium and beyond, Eastwood should’ve been top of the list to capture the pain of “The Bridges of Madison County” – if only because his notorious impatience would have spared years of studio development.
When Steven Spielberg cast the short story before it was published in 1991, his first choice to direct was Sydney Pollack. On paper, landing the director of “The Way We Were” looked like a coup (especially because that film’s star, Robert Redford, had been tipped to play the tale’s aging bachelor, Robert Kincaid), but screenwriter Kurt Luedtke, who had won an Oscar for Best Adapted Screenplay for Pollack’s “Out of Africa,” couldn’t decipher the material. Oscar-winning “Rain Man” screenwriter Ron Bass was the next man, and he also failed to deliver. The project stalled until Richard LaGravenese, a Hollywood staple thanks to “The Fisher King” and “The Ref,” delivered a draft that hit the heartbreaking right notes. It was the version that hooked Eastwood (much to the delight of Spielberg, who had always wanted him for the male lead). Alas, when Bruce Beresford got attached to direct, his “Driving Miss Daisy” screenwriter, Alfred Uhry, spoiled everything Eastwood loved about the previous project. The project was about to fall into development hell.