DEATH OF AUTO-TUNE:
First of all, this is a great parody of the song.
Second, the hook is really great--the way it moves back from guitar to (saxophone? clarinet? it sounds like a woodwind about half the time, and brass the other half).
Third, Jay-Z is raising one of the interesting questions of hip-hop: what's the difference between the good and the popular? Hip-hop has always, on some level, equated quality with popularity; compare that to the standard attitude of the underground/indie scene, where the important thing is to be successful on one's own terms, even if one is less popular as a result. As an example, though Soul Asylum was more popular at its peak than The Replacements, no one thinks that popularity implies anything about the quality of the two groups--if anything, popularity implies mediocrity (James Iha of the Smashing Pumpkins once said "the only way you fill Madison Square Garden is with mediocrity").
Hip-hop is different, because the very best acts (Grandmaster Flash, Run DMC, Public Enemy, NWA, Biggie, etc) are both excellent within the terms of the genre and extremely popular. Even the good but definitely second-tier acts (Digable Planets, say, or The Pharcyde) have a number of radio hits. The very good are always successful. But the successful aren't always very good: Biz Markie, Kris Kross, etc are just as popular in their time as good acts, gaining whatever value novelty has. The function, which Jay-Z has served over the last 10 years or so, of the good act is to remind everyone--listeners and rappers alike--of the pecking order. In this we can say that Auden is wrong ("Some books are undeservedly forgotten; none are undeservedly remembered"--though perhaps our time frame is not yet long enough) and Maugham is correct--whatever our judgments in the future may be, we have to make them out of what was popular.