The cool cat was now rolling with the fat cats... : Jay-Z, Picasso Baby, Frank Sinatra and knowing how to quit while you're ahead

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I've spent the past day thinking about Picasso Baby-gate. I read this beautiful, scathing piece by Sasha Frere-Jones and it was all true. This line was particularly striking: "Those civilians, in another country [victims of U.S. drone attacks], see America the way Trayvon Martin saw George Zimmerman—a force they couldn’t stop physically creating a story they couldn’t fight historically."

The overwhelming anger I feel at the Zimmerman verdict, and towards American foreign policy (now and for the past sixty years), is in violent need of some popular culture expression. This protest song by PJ Harvey about Guantanamo is clearly what we need more of, is what I wish I heard every time I turned on the radio. ("With metal tubes we are force fed / I honestly wish I was dead.") For that matter I would love to turn on the radio and hear Misogyny Drop Dead by planningtorock. Protest is out there, yet somehow endlessly marginalized, hidden away unless you're already looking for it. The closer you get to mainstream, the less really effective protest-rhetoric makes it through.

However, it seems to me, that Jay-Z has never felt particularly at home talking politics. (And not only because of his ongoing desire to become the mainstream.) He spits the occasional political line ("Blame Reagan for makin' me into a monster / Blame Oliver North and Iran-Contra"), but quickly moves onto territory he's more comfortable with (boasting, running his 'army', money, sex, more boasting, and, of course, the further you go back in time, drugs, crime and the streets.)

Daniel Nester had a good line on Facebook: "Everything is interesting about Jay Z except Jay Z."

And I came up with this rather mild quip: "Jay-Z should cover that Modern Lovers song, the one with the chorus Pablo Picasso was never called an asshole."

Then, today, I remembered a Frank Sinatra obituary I read a long time ago in, I think, Rolling Stone magazine (or maybe it was Spin.) In particular, I remembered (or perhaps misremembered) one line, the author explaining why he felt Sinatra had betrayed him, in fact betrayed all of his fans, (I feel it also had something to do with Sinatra's Vegas years): "the cool cat was now rolling with the fat cats." (I'm constantly amazed at these short phrases still in my mind fifteen years later. Though I tried to find it on line, and couldn't, so maybe I simply made it up.)

I wondered if this Jay-Z / Sinatra comparison might lead somewhere. They were both pure entertainers, rags-to-riches aura, their own trademark style, different versions of mafia-chic, false retirement announcements, generally considered to be 'the greatest' in their field. They both started cool and eventually got lame in ways that might have something to do with having lots and lots of money. (That quote by Sinatra where he says what he wants is 'fuck-you money'.) I'm not sure. There are certainly people out there who know so much more about both of them than I ever will.

The Beatles broke up and The Rolling Stones kept going. So The Beatles remain legendary while the Stones most often come across as an embarrassing shadow of their former selves. Tupac and Biggie are dead, while Jay-Z just keeps rolling. (Rock 'n' Roll eventually became embarrassing and perhaps now it's Hip Hop's turn.) Is ongoing reputation simply a question of knowing how to quit while you're ahead?

I actually don't find the Picasso Baby art world cluster fuck all that embarrassing. Jay-Z handles himself well. He looks like he's having fun. But if I compare it to any of his best tracks, I suddenly feel something has gone horribly awry. Then again, I came to Jay-Z really late. The first track that got me was The Takeover ("A wise man told me don't argue with fools / Cause people from a distance can't tell who is who"). I think my favourite track might be the much-too-late-period Trouble ("I try to pretend that I'm different but in the end we're all the same".)

"I try to pretend that I'm different but in the end we're all the same..." It's clear that Jay-Z thinks he can escape his fate, that the same boasts he once made from the streets will remain convincing now that he's a multimillionaire with friends in the White House. And of course they're not. While once they seemed angry, hungry, aspirational, now they feel aimlessly arrogant in an unnecessary, deluded way. Why continue to boast when you already have everything? Why rub our faces in it? I suppose that's what makes it car-crash-fascinating, why I've been thinking about it all day. Most of us will never be as successful as Jay-Z, and therefore have no idea how we would deal with such fame (artistically or otherwise), and clearly he doesn't know either.



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