McSweeney's is a complex combination of things. You are spot on with smug. It is also pretentious but in an ironic way, like they are winking at you (my chief criticism of David Foster Wallace). But I chose sardonic because it includes the cynicism that articles like this one feel full of.
From Wikipedia on Sardonicism [1]:
To be sardonic is to be disdainfully or cynically humorous, or scornfully mocking.[1][2] A form of wit or humour, being sardonic often involves expressing an uncomfortable truth in a clever and not necessarily malicious way, often with a degree of skepticism
I used to love that kind of bitterness, almost like a punk-rock attitude. Maybe my tastes have just changed.
Gen-Z does seem to have a similar dark humor tinged with fatalism and irony. It just somehow works better for me. Perhaps it is mixed there with a kind of earnestness that characterized Millennials that helps to removes the smugness?
1. https://en.wikipedia.org/wiki/Sardonicism