But his outsider status is a selling point, not a liability. Even as it lets him turn the left’s identity politics against itself, it also enables him to flatter each conservative constituency in a somewhat different way, to give each a piece of vindication and play to each with a piece of his persona.
Thus he lets religious conservatives feel, on the one hand, like they’re accepting the realities of the culture war — it’s over, we lost, we need to make allies of gay people instead of scapegoats — while simultaneously suggesting, through his performative promiscuity, his Victorian-decadent relationship with Catholicism, that they were actually right about homosexuality all along. (As the writer Walter Olson of the Cato Institute pointed out recently, a staider sort of gay conservative might actually have less appeal.)
He lets male chauvinists and alt-right tough guys feel vindicated in their hostility to political correctness — see, even the gay guy in drag gets it — while offering a harsh critique of feminism that unlike theirs is free from the accusation that it’s being offered in sexual self-interest.
And when he goes out to Middle America — I recommend watching his visit to Memories Pizza in Indiana, the small-town pizzeria subjected to a two-minute hate because its owners said they might not cater a gay wedding — he presents himself (posh-sounding accent and all) as an ambassador from the cosmopolitan reaches of society, here to apologize for the terrible behavior of his fellow snobs and globe-trotters.
So Milo’s appeal on the right is, one might say, intersectional.