I think I'm plagiarizing from Heraclitus here, but it's in the public domain, so whatever: You can't be scandalized by the same pop star twice. The ones you found thrilling or off-putting, even, will be anodyne to your younger cousins and goofy and gauche to your children. All this is to say that Jay-Z has an extremely earnest and affecting presidential campaign ad out for Barack Obama, and it will make more sense to you the less you remember that Jay-Z began his career as a threatening and somehow amoral figure, like almost every pop superstar in the last 60 years.
My genre of choice is power pop and my favorite album has a lovely cover of "Pure Imagination" on it, so I'm certainly not suggesting that this boundary-pushing quality is necessary or even desirable for good music. But the lesson we seem to have learned, as a culture, from rock and roll is that it's somehow necessary to subvert the expectations of your elders to appeal to the teenagers five to ten years older than you are.
So the narrative goes through each generation--Elvis wiggles his hips amorally and Jimi Hendrix does drugs amorally and Madonna wiggles her hips amorally and Jay-Z sells drugs amorally. Jay-Z survived his competitors in the 90s and the aughts not just because he was supremely talented but because he was a serious figure--an affront to something, whatever it was, where Ma$e was only an affront to moms who looked askance at Parental Advisory labels when their 12-year-old asked for Harlem World.
Ma$e could be immoral, but Jay-Z was amoral; he bragged about selling cocaine, he gave the middle finger to the law, he suggested as recently as Watch the Throne's "Otis" (with its wonderfully ridiculous video) that "everything's for sale / five passports I ain't never going to jail."
Even as he does things that read as selling out when anybody else tries them--astute investments, restaurants, retirements and comebacks and buying the Nets--he only strengthens his image, somehow, as a rebel. The more things he has in common with a private equity guy, the more people who hate private equity guys root for him. Now he's in this--
--as an evocation of the American Dream, which is the weird but inevitable path dangerous super-superstars take when they don't die young.