Why It Took Clint Eastwood 33 Years To Finally Make Cry Macho


Clint Eastwood’s Cry Macho was 33 years in the making. We break down why it took Eastwood so long to finally direct and star in the neo-Western.

Clint Eastwood’s Cry Macho was released in September 2021, but it had a 33-year-long wait before Eastwood finally made the film. Known for making Westerns, Eastwood directed and starred in Cry Macho, a neo-Western about a former rodeo star who agrees to bring back his ex-boss’ son from Mexico. While many films have gone through development hell, Cry Macho has been pitched to studios since the mid-1970s, by screenwriter Nick Schenk and late author N. Richard Nash. Eastwood has been attached to the film since the late 1980s, but why did it take so long for the actor-director to get going on making the film?

Cry Macho had a tumultuous road to the big screen. By the time of its release in 2021, the ongoing pandemic saw it receive a simultaneous dual release — in theaters and on Max (while it was still known as HBO Max). Following decades in development, Cry Macho finally went into production in the fall of 2020, with Eastwood signed on as a producer in addition to his other responsibilities. Prior to Eastwood taking the reins, Arnold Schwarzenegger was signed on to star in 2011; he would have worked alongside then-director Brad Furman. Eastwood joined the project years after initially being offered the starring role. What changed?

Clint Eastwood Delayed Making Cry Macho To Star In The Dead Pool Instead

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Clint Eastwood was approached to direct and star in Cry Macho all the way back in 1988. By then, the film already had a script, but Eastwood opted to make The Dead Pool movie instead (via Variety). The actor-director essentially chose to reprise his role as Inspector “Dirty” Harry Callahan, for what would be the last time, in The Dead Pool rather than play a new character in Cry Macho. What’s more, Eastwood believed himself too young to play the lead role in Cry Macho in 1988 (he was 58), which was why he pitched Robert Mitchum, who was 71 years old, for the role (via Los Angeles Times).


Not having Eastwood attached to play the film’s Mike Milo continued the film being in development limbo. In 1991, production on Cry Macho began, but was never completed. After The Dead Pool, Eastwood’s career kept him busy and he direct and starred in The Rookie, The Bridges of Madison County, In the Line of Fire, Unforgiven, Million Dollar Baby, Space Cowboys, and Gran Torino. When Eastwood finally returned to Cry Macho in 2020, he finally felt he was the right age for it, having grown into the role and ready to revisit the material after three decades. Cry Macho is better because it took so long for Eastwood to make.

Would Cry Macho Have Been A Hit If Eastwood Directed The Movie In 1988?

Cry Macho bombed at the box office, and received an overall negative critical reception. The film was likely affected by its pandemic release — audiences hadn’t fully returned to theaters. It could also be that moviegoers had moved on from Westerns. The genre isn’t as popular now, and Eastwood himself hadn’t made a Western in a long time prior to Cry Macho. He was also a much bigger star back then, so it’s possible it would’ve been better received had it been released in 1988; there was a thirst for Westerns then, and Cry Macho might’ve benefited greatly had it been made while Clint Eastwood was still heavily involved in them.