When legendary producer Albert S. Ruddy (The Godfather, The Longest Yard) first approached 91-year-old Clint Eastwood to play Mike Milo in Warner Bros.’ new uplifting and poignant drama, Cry Macho, Eastwood balked at the project. He believed he was too young to play the one-time rodeo star and washed-up horse breeder. That was 1981.
Now, 40 years later, the timing was perfect for the 91-year-old Eastwood to take on the character.
“This picture came along about 40 years ago,” Eastwood recalls. “Al Ruddy asked me if I would do it and I said, ‘I’m too young for this part, why don’t I direct it and we’ll get Robert Mitchum?’ But it didn’t happen and it just went by the wayside until about two years ago. We brought it back out and I thought it was just the right time for it and I thought it’d be fun to do.”
Forced to take the backroads on their way to Texas, the unlikely pair faces an unexpectedly challenging journey, during which the world-weary horseman finds unforeseen connections and his own sense of redemption.
For Eastwood, Cry Macho is a story of being lost. And found. According to Eastwood, the character has endured the kind of losses in life that would take most men down. Once a circuit star with a wife and family, the hardened cowboy with the well-earned rough-hewn exterior has had to pick himself up time and again, no matter what knocked him off his actual or proverbial horse.
At the end of the day, it’s life’s hard knocks that have made Mike even more pragmatic and, despite a stubborn streak, when given a job to do, like it or not he sets out to do it…albeit in his own way. To Mike, macho is simply a word, not a way of life.
For the filmmaker, a notable element of bringing Cry Macho to the screen was not unlike the journey his character, Mike Milo, must take in the film: one with a few detours along the way.
The story takes place in 1979—an era when Eastwood himself was often straddling cowboy and cop roles, two screen genres he’d help to define, while also taking on more and more films behind the camera. Watch the trailer below:
The screenplay, by Nick Schenk and the late N. Richard Nash, is based on Nash’s book, Cry Macho. The project began decades ago under the stewardship of venerable film producer Ruddy, who paired with Eastwood on Million Dollar Baby. “Nash wrote great characters and I became enamored with this piece,” Ruddy offers.
“The more I got into it, the more I couldn’t forget the story. It was so compelling, the relationships between the characters were so vivid. I went to Clint with it but he didn’t feel the time was right then,” Ruddy added.
Ruddy never gave up on the project, biding his time until the stars aligned, which turned out to be 2019. “The right time for me was when Clint Eastwood called me and said, ‘Do you still have the script?’ And I knew what that meant. There was something about it in the back of his mind that, like me, he couldn’t forget.”
Producer Tim Moore remembers when he and producer Jessica Meier, both with Eastwood’s Malpaso banner, were looking for their next project. Says Moore, “Clint said, ‘There’s this script that Al Ruddy has, I want to take a look at it.’ We brought in Nick to work on the screenplay because he has a history with us, having written both ‘Gran Torino’ and ‘The Mule,’ so he writes well for Clint.”
Schenk—having written an original script, one based on an article, and now a book adaptation for the icon—says, “It’s such an honor to write for Clint, to be trusted with that, so I was happy that they came to me again for this project. We kept going back to find those little moments that were key to understanding Mike, that also felt right for Clint’s version of him. Clint wanted the story to have a dusty, gritty tone that would match the direct nature of the character as well as the tough spot he finds himself in when we first meet him.”
Meier adds, “Clint really wanted to do a story that had the sense of adventure—a sort of hero’s journey not for a young man just setting out in life, but for a man who’s lived a hard life, where things didn’t always work out. He’s been injured physically because of his job in the rodeo, and emotionally because he’s lost his family. He’s down and out, at the bottom of the barrel, but because an old boss he had helped him out before asks a favor, he’s going to do this one last thing for him. Mike’s a man of his word who follows through with his promises—spoken or unspoken.
Despite the time it took, Ruddy, his patience ultimately paying off, couldn’t have been more pleased. “Clint will always be, on a certain level, the great American hero, the cowboy,” he says. “And in everything Clint does, every love story, action film, it doesn’t matter, there honesty. When you see a Clint Eastwood movie there are moments that are so visibly honest, whether they are frightening or they make you laugh or they break your heart, you will always remember those moments.”
Cry Macho is now in theaters and streaming on HBO Max.