Anxiety starts early for pop audiences. For decades, I have had twenty-somethings tell me that they don’t know what’s on the charts, haven’t listened to any new artists since college, and don’t “know anything about music.” They feel confused by how quickly the value of their knowledge of what’s current fades. Weird Al’s songwriting process, almost without exception, is to confront that anxiety and to celebrate it. Yankovic will take a mysterious and masterful song and turn it into something mundane and universal.
Weird Al has been cool for so long because pop makes everybody feel uncool; that he is the only one to admit it has made him a pop star.
Sasha Frere-Jones, “Weirdly Popular”, The New Yorker (11 & 18 August 2014), 92.