I love the part in the beginning of Ocean’s 13 where Reuben tells Bank (played by Al Pacino) that there was a code amongst “guys that shook Sinatra’s hand.” While that ritualistic sensibility might’ve originated with the “friends of mine/friends of ours” sets of old, is has somehow trickled down and made evident again through the likes of Diddy, Jigga, and most recently as part of a promotional campaign for this years VMAs, Drake.

I’m interested not by the reasoning behind the stark, overall gravitation towards Old Blue Eyes- we can all only wish that we embodied an ounce the eternal cool that he was portrayed as having- but more at the fact that hip-hop’s fetishistic transparent obsession with his persona is so recurring. Last week, I had an opportunity to view Drake’s TVC on MTV.com, and the first thing that came to mind (before I could mentally complement it, because it is a dope spot) was “wait, isn’t being Sinatra Jay’s thing?” It’s been less than a year since “Empire State of Mind” hit full swing and the critical mass and mainstream media were obsessed daily with his self-pronouncement of being the “new Sinatra”, creating a storm of rumors that “Empire” would now, or soon, replace “New York, New York” as the city’s consummate psalm.

The funny thing is upon hearing “Empire State of Mind” for the first time last year, I thought, “wait, isn’t that Diddy’s thing?” (I also thought “wait, isn’t the ‘state of mind’ thing Nas’s thing? But from that, I digress.) Out of all the pioneers in Sinatra-ization of hip-hop, Puff is definitely the groundbreaker; we all remember in 2003 when he, Ashton Kutcher, and a finally- recognized-for-his-celebrity Jamie Foxx touted themselves the “new Rat Pack”, socially portraying themselves as Sinatra, Dean Martin, and Sammy Davis, Jr, respectively.  Then, in 2008, he famously reprised that character, copiously, and successfully channeling Sinatra in his campaign for Ciroc:

So, with all these examples having mainstream implications, why has is been acceptable to style jack so transparently (and I mean this in the most non-critical way possible)? Remember on “Big Brother” where Kanye was rhyming about his quiet dispute with Jay-Z because he told Jay he did a song with Coldplay and the next thing he knew, Jay had a song with Coldplay? I would’ve expected that same agitation to appear somewhere in this circumstance, especially since they oft share the same stage. I guess that ultimately, Sinatra has become a caricature to our culture in some capacity; we celebrate the “idea” of Sinatra rather than his artistic achievement. More Halloween than homage.

In closing, and in my humble opinion, I’d most certainly take Puff Daddy, Jaÿ-Z, and Drake over Sinatra 1, Sinatra 2, and Sinatra 3 anyday. Admiration is cool, but let’s not sweat dude.

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