What MutilationWave said is probably the best description of what “liking things ironically” was and the thought process behind it. “I like this thing but I can let other people know so I wear it but pretend to dislike it.”
My opinion is, prevalence of that attitude in the late 2000s/early 2010s was a culmination point of a cultural cynicism that was prevalent in the US during the 90s. That cynicism started in popular culture but filtered into politics and the capitalist system as the status quo got worse. The popularity of Donald Trump or the person that shot that health insurance CEO is because they are seen as authentic even if they might not be, as a the case with Trump.
Late Night With the Devil. Typically I don’t like the devil/possession sub genre but the setting and tone made this one much different and way better.