‘Cry Macho’ Star Clint Eastwood Reveals How He’ll Know When it’s Finally Time to Retire

Rawhide turned Clint Eastwood into a screen legend, and since then, he’s either starred in, produced, and directed more than 50 films. Fans have seen him don cowboy hats, rock Dirty Harry’s suits, and fall in love on screen. His talents have earned him Academy Awards, Golden Globes, and People’s Choice Awards. With Cry Macho as his latest release, the 91-year-old Eastwood is not ready to fold up his director’s chair or give up his acting career just yet.

Clint Eastwood at 'Richard Jewell' premiere
Clint Eastwood | Valerie Macon/AFP/Getty

Clint Eastwood will wait until his movies flop to quit

When has Clint Eastwood not been in front of or behind the camera? It’s a rare thing, and before Cry Macho, fans saw him last in 2018’s The Mule. Both films have him handling some sketchy business in Mexico, but Cry Macho also has Eastwood riding horses, punching folks, and going on a sentimental mission. Further, the film’s theme ties in to his character, Mike Milo’s, views on age. Fitting, as he’s totally cool with it.

During an interview with the Los Angeles Times, Eastwood expressed how his age is a non-factor when it comes to working. “I don’t look like I did at 20, so what?” he said. “That just means there are more interesting guys you can play.”

That doesn’t mean retirement hasn’t crossed his mind. Eastwood has questioned himself at times, and he believes that if he releases a few duds, it’s a sure sign to throw in the towel.

“What the hell am I still working for in my 90s? Are people going to start throwing tomatoes at you? I’ve gotten to the point where I wondered if that was enough, but not to the point where I decided it was. If you roll out a few turkeys, they’ll tell you soon enough,” he told the L.A. Times.

Eastwood originally turned down ‘Cry Macho’ because he was too young

Eastwood is the main character in Cry Macho, but a producer tried to persuade him to take the part way back in 1988. But he shot it down and instead wanted to parlay it into a directing opportunity. “I’m too young for this. Let me direct and we’ll get Robert Mitchum, an older dude,” he said.

Mitchum was in his late 60s at the time, and the project didn’t move forward with him either. Cry Macho had a few false starts over the years with other actors, but Eastwood finally decided the time was ripe for him to step into the lead role.

When and where to watch ‘Cry Macho’

Cry Macho drops on HBO Max and in theaters on Sept. 17 with Eastwood as Texas cowboy Mike Milo. According to the film’s logline, it’s adapted from the 1975 book:

Based on the book by the same name, Eastwood stars as a one-time rodeo star and washed-up horse breeder who, in 1979, takes a challenging journey, during which the world-weary horseman finds unexpected connections and his own sense of redemption.

Fans can expect to see the brooding, serious Eastwood they’ve come to love over the decades in this border-hopping adventure. And they can also expect to see more of his work — unless it’s a turkey.

RELATED: Clint Eastwood’s Early Hollywood Career Involved Digging Swimming Pools and Driving Garbage Trucks