Clint Eastwood is on stage at the Republican National Convention having a very weird conversation with an empty chair next to him. It’s 2012. He’s going on about Guantanamo Bay. He says that Joe Biden is “just kind of a grin with a body behind it.” In the middle of this, he’s interrupted by a shout from the audience. “Clint, you made my day!” One imagines that this has happened to him thousands of times since the release of Sudden Impact in 1983. “I don’t say that word anymore,” he replies. The audience laughs. He pauses. He smiles. It’s always a little weird to see Eastwood smile. “Well, maybe one last time.” As he winds his speech down, he can’t quite make good on his offer. “Alright, go ahead,” he says, gesturing to the audience. A hockey arena full of Willard Mitt Romney supporters shout “Make my day!” back at him.

It’s an apt demonstration of the way that Eastwood’s gunslinging vigilante persona has endured over the decades. As The Man with No Name in Sergio Leone’s Dollars trilogy, Eastwood ceaselessly trots through the west, killing people firstly for money and secondarily because they deserve it. As Detective Harry Callahan—his friends call him Dirty Harry—he’s the lone cop who can get it done. Pauline Kael observed that only Harry himself “knows what justice is and how to carry it out … He is our martyr–stained on our behalf.” His famous lines—the aforementioned, “You’ve gotta ask yourself one question: ‘Do I feel lucky?’ Well, do ya, punk?”—are preludes to lethal violence.

These characters are some of the most famous and beloved in film history and perceptions of Eastwood are unavoidably tied to them. Such is life for an übersuccessful leading man. But as he continued working into his nonagenarian years, his movies have increasingly revised and rejected the attitudes that once defined him onscreen.

In Manohla Dargis’s review of Gran Torino (2008) for the The New York Times, she observes that “Dirty Harry is back, in a way … not as a character but as a ghostly presence. He hovers in the film, in its themes and high-caliber imagery, and of course most obviously in Mr. Eastwood’s face.” Eastwood plays Walt Kowalski, a recently widowed Korean War veteran. He’s isolated, alienating his kids and grandkids (because they’re terrible), his priest (because he’s “a 27-year-old overeducated virgin”), and his neighbors (they’re Hmong immigrants and he is incredibly racist). He eventually finds common cause with the family next door after intervening to get a gang to stop bothering Thao, their teenage son.

In an effort to get the gang to leave his neighbors alone once and for all, Walt confronts and beats one of the leaders. (How does a guy who’s nearly 80 beat up a 20 year old gang member? Don’t worry about it). When the gang responds by shooting up his neighbors’ house and raping Sue, their teenage daughter, Walt prepares for a climactic confrontation. Thao joins him in preparing, hoping to get revenge on his tormentors. As Walt is leaving, he locks a furious Thao in the basement. The kid cannot be a part of this, he explains:

This monologue, which would probably make Dirty Harry sick, is only the preamble. When Walt confronts the gang members, he is unarmed. They gun him down in front of the entire neighborhood. Walt dies on the ground, legs straight down, arms spread wide. A police officer informs Thao and Sue that with all the witnesses they will finally be able to convict and imprison the gang members. The ending is a mirror image of Unforgiven (1992), where Eastwood as William Munny guns down a saloon full of enemies by himself. Confronted with a similar amount of adversaries, killing them—if he even could at his more advanced age—no longer seems like a viable means of ending the cycle of violence that haunts the neighborhood.

The Mule (2018) takes a more roundabout approach to confronting his past persona. He plays Earl Stone, another Korean War vet alienated from his family. He ruined his marriage and his relationship with his daughter because he was too busy traveling the country as a hotshot horticulturist, hanging out with his flower-growing buddies instead of spending time at home. Eventually, his farm is foreclosed on and he’s got nothing to show for all those years of abandonment. Because he needs money, is a good driver, and has a lot of time, he becomes a drug mule for the cartel.

This alienation leads Stone to advise any young person he can find to avoid being like him. After a long night of partying at the cartel boss’s home, Stone finds his handler, Julio, sitting by himself. Stone offers him simple advice: walk away. Enjoy life. These people don’t care about you. Work isn’t important. He is forcefully rebuffed.

Later, he runs into DEA agent Colin Bates, played by Bradley Cooper, at a Waffle House. He’s there because he’s pursuing the titular mule but he doesn’t suspect Stone. Bates looks at his phone and says “Oh shit.” Stone overhears and says “I know a lot about ‘oh shits.’” Stone solemnly advises him:

Earl opens up to Colin more than he did to Julio and his advice is received more warmly for it. But neither younger man has the same association the audience has, the same memories of Eastwood as one-man-band cops and outlaws. The regret in his voice reverberates through his nearly seven decades of work.

In Cry Macho (2021), his most recent and perhaps last starring turn, Eastwood plays Mike Milo, a former rodeo star who descends into deadbeatery after his wife and kid die in a car accident. As a favor to his former rodeo boss he heads to Mexico to try and retrieve his boss’s son from his vindictive and abusive mother. The kid, Rafo, has a rooster named Macho who is his closest companion. Mike initially laughs at this—“Guy wants to name his cock Macho that’s okay by me”—but the priorities it implies eat at him throughout the movie. Eventually, he issues a full-throated rejection of the worldview that defined Eastwood’s most iconic characters:

Past 90 during filming, Eastwood walks like someone who hit the ground too hard a few too many times. In his younger days, his characters’ deliberate pace was an expression of their confidence and invincibility. Now, it’s a reminder of the toll that living harder takes. Still, the clearest place his age shows is not in his movement but in the way he talks. His characters are more prone than ever to monologuing and they take their time doing it. Eastwood pauses and circles back, catching his breath and trying to stay focused. It can feel, at times, like the more reflective mode was forced on him by an inability to cleanly spit one-liners.

Offscreen, he still won’t say quite as much. In a 2021 interview by Mara Reinstein in Parade, Eastwood was asked what he thought of his former tough guy persona. “I’m not that self-analytical,” he said. “But sometimes I look at the characters, like Dirty Harry, and I wonder about their feelings.” This only seems like a vulnerable answer in the context of Eastwood’s historical brevity and deflection. What does he wonder about their feelings? Reinstein doesn’t follow-up and he probably would have shrugged if she did. His onscreen work over the past 15 or so years will have to serve as his elaboration.

He will always be best remembered for the hard nosed movies he made in the 60s, 70s, and 80s but the more vulnerable movies he made in his 70s, 80s, and 90s will stand as his most soulful. It’s unlikely a stadium full of losers will ever shout a line from The Mule back to him, but that’s probably a good thing.