Aside from the obvious reasons -- creator of the "Missing Manual" book series, New York Times Circuits columnist, all-around-great guy -- he does one thing no other tech pundit can pull off: he parodies well-known songs and turns them into tech classics. He usually debuts a new one every year at Macworld, and each year they get better and better.
And Pogue's done it again, this time creating an original music video called "iPhone: The Musical" about the drudgery of owning a Phone of Yesteryear, longing for an iPhone, and finally making the glorious purchase. Both the song and video -- some of it recorded with guest singers at the Apple Store Fifth Avenue iPhone launch -- are incredibly clever and humorous, and definitely worth a watch.
You can also check out some of Pogue's older song parodies at his website.