Cry Macho Synopsis: A one-time rodeo star and washed-up horse breeder (Clint Eastwood), takes a job from an ex-boss to bring the man’s young son home and away from his alcoholic mom. Crossing rural Mexico on their back way to Texas, the unlikely pair faces an unexpectedly challenging journey, during which the world-weary horseman may find his sense of redemption through teaching the boy what it means to be a good man.

At 91-years young, Clint Eastwood’s iconic career continues to chug along. His grizzled presence will forever remain a fixture in Hollywood’s history, but actor-turned-director has endured some struggles during the twilight of his career. Well-meaning features like 15:17 To Paris, Sully, and Richard Jewell have reduced Eastwood’s vast skillset to dramatically middling showcases. 

Eastwood’s latest, Cry Macho, delivers the star’s long-awaited return to acting. There’s a quiet poeticism at the core of Macho – a neo-western that connects Eastwood to the genre he spotlighted during his heyday. While the film presents innate promise, wishy-washy execution hinders this road trip from ever taking off. 

Even with the film’s misgivings, Eastwood remains a singular force onscreen. As the washed-up former cowboy Mike Milo, Eastwood gravely voice imbues longing with every reflective remark. The character’s inner turmoil balances effectively through the actor’s deft comedic touch. Few deliver sharp one-liners with such gritty panache – as Eastwood showcases the movie star energy that has driven his esteemed 60+ year-career. Co-star Eduardo Minett also holds his own as Rafo, sharing a genuine rapport with Eastwood that slowly builds from their initial distrust.

I can see why Cry Macho was an intriguing proposition for Eastwood, as the film presents itself as a subversive, neo-Western take on Mike’s (and Clint’s) legacy amidst their waning years. When screenwriters Nick Schenk and N. Richard Nash lean into this conceit, the duo extract moments of gentle poignancy from the actor’s spiritual connection with our washed-up protagonist. Eastwood and Cinematographer Ben Davis also elicit quiet beauty from their clever repurposing of Western iconography – often finding rustic glimmers of life within each worn-down location. 

Cry Macho is perhaps Eastwood’s best effort since American Sniper, yet the project still struggles to play to its strengths. Schenk and Nash lay out a promising narrative blueprint – only to throw several bumpy narrative detours along the way. Constant interjections from emptily menacing foes often detract from the film’s quieter appeals, with the film coming to a halt every ten minutes or so to introduce a needless sense of conflict. It’s a shame that the screenwriters don’t trust their material enough to embrace its thoughtful nucleus. 

For a film that flashes moments of meditative insights, Cry Macho settles far too often on inert melodrama. The script leaves most of the heavy lifting on the performers to dig under the surface of their rigid facades. There are scenes where that strategy works well enough, but the simplistic writing reduces everything to mild pleasantness rather than providing a genuinely moving experience. 

Cry Macho doesn’t work as intended, although the film’s breezy qualities do pack a certain allure. It’s a suitable low-investment watch for HBO Max users looking to drift along with Clint for two hours. 

Cry Macho is now playing in theaters and on HBO Max.

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