Libertarians are typically more culturally liberal than conservative,
I'm not sure where you get that idea, but we're treading dangerous waters here, forumically.
Libertarians are generally very right-winged. Their major drive is "
less state, less taxes", which also means "
less social support, more social darwinism, if you're poor in a free market then you deserve it" with the idea that moral virtues lead to wealth. They are neoliberals, which is the opposite of liberals
(to make things more complicated, of course, the word "liberal" in the USA means leftist, whereas in Europe it means ultra-capitalist - not even illogically : it's about "liberty" and everyone is pro-"liberty", but given how many freedoms are mutually exclusive, it's all about which ones a "freedom-lover" defends at the expanse of which ones).
But one source of confusion is also the fact that these words flatten everything onto one axis. Political positioning is usually made on
two axes, one being economic freedom, and the other being lifestyle freedom. People's positions are often situated along a diagonal (usually socially progressive people have the state control a lot of the economy, and socially conservative people usually want free market), but communists tend to be very controlling in both private freedoms and commercial freedoms, and libertarians tend to be very permissive in both.
Still, the economic axis is usually the one that most determines political affiliations, when it comes to left/right political parties (parliaments tend to be organised around this one main axis).
Then, there's the self-identification to a political side. Left-wing people praise themselves in being left-wing, right-wing people praise themselves in being right-wing. Less than descriptive, labels become their own rewards, and a stake of "loyalty" or "betrayal". Strangely often, people simply vote in knee-jerk accordance to which label signifies "the good guys" in their book, according to their parents, peers, etc. And so, you can have staunch proponents of one side holding sensitivities of the other, but still framing them accordingly to their pre-defined voting choices. And this kind of investment in a political identity is particularly strong in times of polarized "culture wars" ("
you sound like one of THEM"), or when family stories are anchored in civil war histories ("
THEY killed my grandpa"), etc. See how many people filter facts (on covid, on ecology, on gender violence, etc) based solely on "which political side says what" - and even try to politically situate objective facts (or their implications, or their information origins) before acknowledging or rejecting them.
So, a traditional Republican or a traditional Democrat will generally take the stances that make him or her sound most Republican or Democrat to their peers and to their own ears. Especially when "their side" is under attack. And, by the same logic, will be reluctant to make concede anything to what is labelled "the other side", by fear of betraying their peers or weakening their invested identity.
And then, there's also nationalism. In both traditional conservative and libertarian versions of the right, there's a strong value put on strength, manhood, "macho" values, etc. You know, gun protection, autonomy, dominance, and the protective role of the patriarch (the family's or the State's). Which also means that, in contexts of geopolitical crises, such as the Cold War or the post 9/11, both value armed chestpounding and manly self-affirmation more than pacifism, analytical hesitancy, blame sharing, and other "wimpy" nuances. And Eastwood went full "war on terror" on a few of his recent movies. When the militarist drums of patriotism are beaten, they tighten a bit people's values, identities and affiliations.
So. In short :
1° Libertarians are generally right-winged, and the Republican values on economy are more important to their core than the Democrat values on lifestyle diversity.
2° Plus, Eastwood is a faithful self-identified Republican who will close ranks in times of crisis.
3° Plus, Eastwood is a reagan-era patriot who will more easily support a dirty harry geopolitical response than showing "signs of weaknesses".
4° Also, he's an old school conservative with values from the John Wayne era. He's 91 years old, of course he doesn't have the same sensitivities as the next generations of Eastwoods. He hasn't been socialized the same way.
So, I really don't see anything confusing in his conservatism. On the opposite, he always surprises me when he nuances it and shows a very strange, touching reflexivity on characters where he both mocks and justifies himself.
All his recent themes are studies of impossible moral dilemmas, but impossible dilemmas in real time situations, where you cannot afford an 6 months ethics seminary to cleverly untangle them. Real time situations where you have to opt for one of the unsatisfactory options, and then will be judged for it by people who have had all the time in the world. But... in a way, it also feels like his take on life, and his own in particular. A blink-and-you-miss-it lifetime (like ours all) where we have to choose what we are, say, think, feel, based on what we have at hands. As the communist poet Louis Aragon wrote : "
by the time one learns to live, it's already too late". Eastwood is a product of ancient cultural constraints, his eyes open on the current cultural constraints and the discrepancies between both. My impression is he knows he isn't free from them, he know we aren't free from ours, and he hangs onto what seems to make (or used to make) most sense to him, as his feet lose stability on those shifting grounds he describes. His contradiction is that, even in uncertainty, he prefers to express a strong opinion than a timid one. I think it's very existential, a matter of self-affirmation. It's what being a man means to his eyes. Right or wrong, he prefers to make a choice, in the instant of life, rather than feeling inhibited by doubt.
His films and his life are in this hesitation. In this hesitation, he knows he doesn't always make the ideal choice. His movies tell us he knows. His movies also tell us to piss off with our judgments on that.