Death of Autotune: Jay-Z’s Sinatra Moment


It’s no secret that I’m a Jigga devotee.  Jay-Z was just breaking out with Reasonable Doubt when I began to seriously tune into hip-hop, having missed most of the East Coast-West Coast feuding of the early-to-mid-90s.  I loved Biggie and Nas and found myself more or less gravitating toward the East Coast side of the debate, but to me Jigga was the lyricist who truly dominated the late 90s and early 2000s.

He had an undeniable flow and partnered with the best producers. “Can I Get A…” was possibly the greatest, nastiest indictment of materialism ever in a genre that has generally been addicted to bling, while eschewing the dour lectures of Dead Prez and other “conscious” rappers; “Indian Night Rider” was the grooviest screed against Dubya’s foreign policy; and The Black Album the ship that launched a thousand gonzo remixes.   Even if Jay and Bey may be obnoxiously aristocratic in their rule of pop culture today, and up to their ears in hock to the Illuminati, I still love HOV’s music.


Listening to “D.O.A. (Death of Auto-Tune),” one of Jay-Z’s late-career classics, I realized there is a striking historical parallel: Frank Sinatra’s “My Way.” Old Blue Eyes had been the prince of pop culture in the pre-rock era, part of the transition of Italian-Americans such as Frank Capra and Marlon Brando from marginalized white ethnics to paragons of the mainstream in the 1940s and 1950s.  Even after the rise of rock and roll left Sinatra a suddenly hokey footnote to the zeitgeist of the times, he kept plugging along.  And “My Way” was his macho, self-indulgent anthem–a declaration that he didn’t give a shit if he was old and outdated, because he did it his way.  Penned by Paul Anka, and based on the tune of a French song by Claude Francois, “My Way” became an unlikely hit for the aged crooner in 1969, and was subsequently covered in grandiose punk style by Sid Vicious, who imbued it with his own sloppy, don’t-give-a-fuck vision.

And now, the end is near
And so I face the final curtain
My friend, I’ll say it clear
I’ll state my case, of which I’m certain

I’ve lived a life that’s full
I’ve traveled each and every highway
But more, much more than this
I did it my way

Regrets, I’ve had a few
But then again, too few to mention
I did what I had to do
And saw it through without exemption

I planned each charted course
Each careful step along the byway
And more, much more than this
I did it my way

“Death of Auto-Tune” is, in many ways, Jay-Z’s “My Way,” but it distinctly lacks the note of self-pity and resignation that marks Sinatra and Anka’s song. Jigga may be way past his prime as a rap artist, but he still wants to put his rivals on notice (“I want niggas to feel threatened”).  He disses other rappers for going soft (“You niggas’ jeans too tight/You colors too bright, your voice too light”), in what always seemed to me to be a dig at Jay’s blipster protege, Kanye West. (Indeed, Yeezy did a whole auto-tune album. Who else is he talking about?) “Get back to rap, you’re T-Paining too much.”  In this blast of bravado, Jay-Z even invokes Old Blue Eyes himself:

This ain’t for iTunes, this ain’t for sing alongs
This is Sinatra at the opera, bring a blonde
Preferably with a fat ass who can sing a song

For an artist who had made a pretty penny selling records and ascended to the heights of cultural influence, it is rich to hear him vow, “My raps don’t have melodies/This should make niggas wanna go and commit felonies.” All the while a tunefully incongruent jazz sample plays in the background, as if to underline his own defiant old age.

In the song, H to the Izzo actually disowns his newfound wealth and power. In one memorable line, he reflects on his humble origins and scorns rappers who try to be “real”: “I don’t be in the project hallway talking about how I be in the project all day.” And then he disses his “political connects,” saying the song “ain’t politically correct.” But the track is no less a declaration of embattled and unrepentant masculinity than Sinatra’s old anthem–the sound of a proud public figure defending his reputation in the face of a new generation.  The only difference is that Sinatra did it his way, while Jay-Z makes declarations about what he will do: “I might wear black for a year straight, I might bring back Versace shades.” Whereas Sinatra was looking back on the past, HOV looked ahead–boldly and maybe even arrogantly. Which of the two was really more delusional?


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