A Supposedly Fun Thing I'll Never Do Again: Essays and Arguments by David Foster Wallace:
Irony in postwar art and culture started out the same way youthful rebellion did. It was difficult and painful, and productive—a grim diagnosis of a long-denied disease. The assumptions behind early postmodern irony, on the other hand, were still frankly idealistic: it was assumed that etiology and diagnosis pointed toward cure, that a revelation of imprisonment led to freedom.
So then how have irony, irreverence, and rebellion come to be not liberating, but enfeebling in the culture today’s avant-garde tries to write about? One clue’s to be found in the fact that irony is still around, bigger than ever after 30 long years as the dominant mode of hip expression. It’s not a rhetorical mode that wears well. As Hyde (whom I pretty obviously like) puts it, “Irony has only emergency use. Carried over time, it is the voice of the trapped who have come to enjoy their cage.” This is because irony, entertaining as it is, serves an almost exclusively negative function. It’s critical and destructive, a ground-clearing. Surely this is the way our postmodern fathers saw it. But irony’s singularly unuseful when it comes to constructing anything to replace the hypocrisies it debunks. This is why Hyde seems right about persistent irony being tiresome. It is unmeaty. Even gifted ironists work best in sound bites. I find gifted ironists work sort of wickedly fun to listen to at parties, but I always walk away feeling like I’ve had several radical surgical procedures. And as for actually driving cross-country with a gifted ironist, or sitting through a 300 page novel full of nothing but trendy sardonic exhaustion, one ends up feeling not only empty but somehow … oppressed.
Think, for a moment, of Third World rebels and coups. Third World rebels are great at exposing and overthrowing corrupt hypocritical regimes, but they seem noticeably less great at the mundane, non-negative task of then establishing a superior governing alternative. Victorious rebels, in fact, seem best at using their tough, cynical rebel-skills to avoid being rebelled against themselves—in other words, they just become better tyrants.