You're supposed to feel conflicted between the obnoxious tone and the rational message. The writing makes fun of know-it-alls while also making a well reasoned argument.
maddox.xmission.com
Of course it's easy to rant and monologue. Dozens of TV presenters do it but sometimes it's very easy to find fault in their subjectively humorous generalizations.
http://maddox.xmission.com/c.cgi?u=bob_dylan_is_a_podcaster
Blowing in the wind, the first song that comes to mind, doesn't fit this at all.
A quick Spotify search through the most popular songs and I can't find any in 10-15 that fits that example soundbite he used, to extrapolate this "emperor's got no clothes" argument on bob Dylan.
I'm not particularly a fan of Dylan except a song here and there I like (looking at the list), but it just shows the style over substance and strength of argument.
To this, someone will call "don't be such a buzzkill, it's just a joke" and that's fine but then you've left the land of making valid points and into the self congratulatory "ironic" content.
I didn't miss the point, it seems, but you did miss mine.