Clint Eastwood, one of the greatest actor/filmmakers of all time, doesn’t know how to quit.

At 91, the two-time Academy Award winning director makes history by being the oldest person ever to star above the title in a movie with Cry Macho, which arrived in theaters and on HBO Max this past weekend 50 years after the debut of his directorial debut Play Misty for Me in 1971.

Eastwood has become famous as a quick filmmaker, opting to lock in scenes in as few takes as possible. While the degree of difficulty to maintain quality in such a rapid pace is hard enough, it’s even harder when Eastwood is directing himself and isn’t able to watch scenes play out from behind the camera.

This causes some issues in Cry Macho, a wonderfully shot film that places Eastwood in the center of the frame for 100 minutes as a former rodeo star and ranch hand coerced into traveling to Mexico in hopes of reuniting an old friend with his teenage son. As the aging Mike and brash youth Rafo make their way to the border, they both learn about themselves, each other and what it means to be macho.

Eastwood’s age often gets the better of him as Mike, a man whose days of cowboying should have been ten to twenty years in the past rather than thirty or forty. This awkwardness makes it difficult for audiences to not feel Mike too brittle for the journey he partakes, especially as he stumbles around trying to catch a rooster, bend down to check beneath a car or ride a wild stallion.

But because it’s Eastwood and because it’s impossible to separate the man himself from the character he’s portraying, viewers will latch onto Mike relatively quickly and forgive these shortcomings as an eccentricity rather than a fatal flaw.

Eastwood is effortlessly transfixing to watch, balancing a rough exterior with a gentle undertone better than any western actor. It’s as if viewers are seeing Eastwood confront his own filmography covered with bravado and machismo and struggling to figure out what to do when the fire begins to smolder.

Eduardo Minett challenges Eastwood every step of the way as Rafo, the aimless teen fending for himself on the streets of Mexico City. Though the screenplay somewhat neuters Rafo’s unbridled personality by limiting him to simple false bravado, Minett does a solid job of matching Eastwood’s tone.

His performance is not exceptionally showy although Minett is capable of being both a worthy pseudo-antagonist to Mike as well as a misguided soul that audiences can feel a sense of compassion toward.

Cry Macho suffers from a narrative perspective, where audiences are forced to accept wild leaps of unlikely responses to situations that feel logically impossible. It’s hard to imagine the events of the film playing out without Mike being seriously injured or killed within the first act.

This also extends out to the supporting characters themselves who feel like afterthoughts in terms of motivation or purpose outside of being narrative plot points. Mike and Rafo are clearly fleshed out both in the screenplay and in the larger film itself, but many of the smaller parts feel ripped from the pages of an old western: the nosy buffoonish sheriff, the strong-willed yet submissive love interest, the friend willing to send the protagonist out to die in order to make a quick buck.

Cinematographer Ben Davis uses natural lighting to create a number of artistic, visually engaging shots that help profile Eastwood as the sun sets on his career. It’s moments like Mike camping out underneath the stars set to the tunes of composer Mark Mancina’s terrific score or slow dances with Mike and Marta in a dust-filled room that will leave viewers breathless.

If Cry Macho is the final film in Eastwood’s illustrious career, then it serves as a solid coda worthy of his generational talent, especially when paired with his other later years self-reflective melancholic pieces Gran Torino and The Mule. The visuals are worthy of checking out on the big screen, although they don’t lose any luster in an at-home viewing on HBO Max.