It would require the right to be proactive instead of reactive.
The primary issue with politics is that while the left had historically been reactive, there is now a specific element of their culture focused on finding, and broadcasting things for their group to respond to.
The right has no such element, and doesn't respond even while facing consistent abuse from aggressive elements.
Tldr:
Gamers.
Rise up.
This is a good point. The right wing is (or seems to be) smaller than the left wing + left-leaning middle, and even among the right wing, a large percentage of those are of the vacuous, vaguely American-Exceptionalism types who can't really give a defense of the American system, they can just complain when it gets torn down. When a statue of an American historical figure (who also may have been a racist) gets torn down, their defense is, "Well, this statue's been up for such a long time, but maybe we could put up a plaque explaining that he had some good qualities and some bad qualities that are totally odious to today's standards and that I completely disavow, and if you want to tear the statue down, you have to do it LEGALLY" instead of working in a framework that allows them to defiantly reject the issue as a problem altogether: "We recognize all of the great figures who had a hand in building the history of this country, and none of you who want to tear down this man's statue are ever going to do anything nearly as significant as what he accomplished, no matter your opinion of his ideas or actions that are totally tangential to his contributions that we wish to recognize. Let's create additional statues so that future generations can see the progress of our country in its totality."
The Right can produce culture any time it wants too, the issue is the means of mass production and distribution are controlled firmly by the Left. Even worse, a specific faction of the Left that constitutes a dogmatic, if non-theistic religion. Not only will they not allow any cultural production that deviates from their orthodoxy, they will actively seek to destroy anyone that even tries to produce it within or without their organizations. Then they will seek to destroy the persons extended family too. And if allowed, kill them. We are not to THAT point yet, but we are pretty close. They are already enforcing the concept of blood guilt, and once you start doing that finding bodies in the street is not too far off.
I think this is a big part of the problem. It's funny that, in Robin DiAngelo's "White Fragility" anti-racism textbook, she uses as evidence that our society is run by White Supremacy the fact that the "people who determine which books we read" are 100% white, but if you actually tried to publish a book that was arguably pro-white, it wouldn't go anywhere. Try to publish a fantasy novel that inspires the imagination of the European-descended people today, and it'd get thrown back by the publish for being "too white, too male, not enough disabled persons representation," whatever. Or, you can publish a mildly pro-Conservative work of nonfiction, but only if it's yet another boring take on "campus culture warriors" or complaining about how you got canceled, and it will sell 2,000 copies that never get read.
This points to the idea that I've seen tossed around a lot, which is that we need "parallel institutions" to allow right-wing thought and creative expression to actually have a platform, or for students to go through college without having to make diversity pledges or give their personal pronouns. But you need capital for that and a concentrated number of people to get it going, and the people interested are spread all over, and there just isn't the capital to get it started. Progressivism has been entrenched in mass culture (where the capital is) for so long, and the corporate monopolists are either hard-left (socially, not economically) themselves, or they're centrist/apolitical but know which way the wind is blowing. Leftists will celebrate the CEO of Goldman Sachs making a boilerplate announcement about Diversity & Inclusion but will demand that some wagie get fired from his job for expressing a heterodox opinion publicly.
As someone who has flirted with "right-wing" beliefs in the past (and still has a few conservative impulses), and a fan of the arts, the reason there are no great right-wing artists or entertainers today is because:
1. "Right-wing" isn't a coherent ideology or a set of beliefs. As a lot of other people pointed out, the four people you named have vastly different ideas.
2. What constitute right-wing thought today, especially in America, is not conducive to artistic value.
More on #2. "Right-wing" today means defending Liberalism, and Neoliberalism in particular. Economic Liberalism is largely based on accumulation and expansion, not the search for truth and beauty that is the basis the arts. The thought of someone like Ben Shapiro or Dennis Prager is largely about assuring you that Economic Liberalism isn't as bad as you think it is, and those that attack it are the problem. Great political art usually comes out of the desire that the paradigm we are living under needs to change, whether that change goes forward or backwards. Certainly, there were great right-wing artists of the past (arguably T.S. Eliot, Ezra Pound, Dostoevsky, Balzac), but they weren't telling you how great capitalism is and how those that dislike it are the problem. Rather, they were illiberal and looked either to the pre-modern past or a revolutionary future as an antidote to the present conditions. No one wants to read a book or watch a movie telling you how great things are. That's how you get shit like Atlas Shrugged. As it currently stands, the Right has no coherent counter to liberalism, and even when it gets market-critical it tends to be so in a rather toothless way. The Left will beat them to that every time.
MDE: World Peace was kino, though.
I agree with this. Spiritually right-wing art has nothing to do with the Republican Party, or Reaganomics, or Ben Shapiro in a suit talking about "facts and logic." A lot of mainstream Republicans would be scared of right-wing art because they are spiritually vacuous and aren't really intellectually or philosophically Conservative, they were just brought up to favor the right-leaning side of American politics during the 80s-2000s, during which time "conservative" meant "Low taxes, poverty is your own fault, count yourself lucky that you have the opportunity to work for a multinational conglomerate that displaced all of your local business." Real "right-wing art" would come out of the movement that I think has been growing over recent years but is mostly relegated today to esoteric artists/thinkers on Twitter with absolutely no reach beyond that. Part of the problem is that the crowd is so small and that they spend so much time tearing each other apart instead of seeing themselves as a cluster of thought and art that is opposed to a much larger opposing force.
Some examples of arguably right-wing contemporary art:
-Heavy metal (death metal, folk metal; art that is focused on the aggressive aspects of human psyche or on celebrating national heritage)
-Films like Interstellar, which is set in a dystopian managerial world where they deny past achievements like spaceflight and try to keep them myopically focused on immediate problems: a lot of left-wing thought today is captured by moralistically shaming people who dare to think about the long-term human achievements like space flight because it's been historically non-inclusive, or we need to give all that money as reparations to black people, or space colonization is icky because it reminds them of the Colonial Era, etc.