Welcome to the 63rd issue of Backseat Freestyle. This is my weekly hip-hop newsletter I send out every Friday(ish) featuring a deep dive analysis on one big thing that happened over the past seven days. I also include a roundup of links to what I’ve been listening to, reading and watching. You can check out the archive, here, and read more about me, here. If you’re already a BF subscriber, thank you for your continued support. If you’re arriving to this issue by way of a forward, LinkedIn or social media, please subscribe below. And please share this newsletter with your circle so that they can enjoy it; personal referrals go a long way toward my goals for growth. With that said, let’s get into it….

EDITOR’S NOTE: You’re prolly like, Ayo, my man, about time you write something! And you’d be right. My last post was after the Super Bowl. Since then, I signed on to be the EP of Hot 97’s new morning show, Mornings With Mero. It’s time consuming to build a new show, but I’m aiming to entertain/inform the city while amplifying Mero’s talents and I’m tweaking the format along the way until I find the right balance. It’s been an amazing experience, so far. Tune in and check out the Hot 97 YouTube to follow along.

SPONSORED: You can’t hide from Father Time. In fact, that’s a central theme of my essay today. It’s a privilege to earn those years. But, sure, sometimes, you look at your photos and think…that’s me but not exactly me. If that’s the case, there’s lifestyle changes you can make. Feel free to click on the link below to learn more. In full transparency, simply clicking helps me earn revenue. Do your boy that favor.

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Front Seat

This is what’s driving hip-hop this week….

FATHER TIME REMAINS UNDEFEATED is one of the great idioms in sports. It a reference to the physical limitations of mankind. Michael Jordan was beset by a cranky knee; LeBron’s back is starting to bark like a Beagle. But you don’t have to make your bones on the court to know that time is not on our side. Take Jay-Z, for instance. The rapper’s last solo offering was way back in 2017. Sure, he’s put out verses here and there. But he’s been relatively inactive for what amounts to a generation or two (maybe even three!) in social media years. So as the societal views on capitalism, morality and social justice evolve and shift among the younger set, his long track record is not solely a marker of his success but fuel for those with active fingers and an iPhone. Now that the volume has perhaps become too loud for his liking, Jay is grabbing the mic to have his say during his three-night run at Yankee Stadium following his headlining appearance at The Roots Picnic. Friend or foe, yo?

🚙 🚙 🚙 🚙

Back Seat

Respect my mind or die from lead shower.

TTHE FIRST TIME I SAW JAY-Z IN CONCERT, was November 28, 1997 at the then CoreStates Center in Philadelphia. Three weeks earlier was the release of his sophomore album, In My Lifetime, Vol. 1, and here he was, one of a handful of opening acts on the No Way Out tour. The stage was curtained off for the headliners, so Jay had to make do with a space that was slimmer than that chick in Calvin Klein pants is. He wore a white T-shirt, baggy raw denim jeans, white Air Force Ones and a bulletproof vest as he calmly paced back and forth rapping “Where I’m From.” while the crowd filtered into a brightly lit arena. The audience and Jay both prolly wondered what he was doing there. He didn’t have the massive hits that were running rap at the time like another opener, Busta Rhymes. But he had the presence of an MC who demanded the crowd hang onto his every word. 

As the lore goes, Jay left the tour before it wrapped to ensure he’d never be an opener again. He went off to work on Streets Is Watching and revamped his attempt at sampling ‘80s records, swapping out Babyface’s “Sunshine”/his “(Always Be My) Sunshine” for Talking Heads’ “Once In A Lifetime”/his and Memphis Bleek’s “It’s Alright.” A few months after that, Vol. 2…Hard Knock Life arrived and Jay was on the (wider) map. 

That moment and story came to mind as I watched him at Yankee Stadium for the second leg of his three-night Jay-Z 30 run. This night was in honor of the 25th anniversary of The Blueprint album, his crowning project that cemented his position in hip-hop’s hierarchy. A helicopter circled high above the sky, with a spotlight scanning the capacity crowd and a camera mounted underneath its carriage to broadcast the images of screaming concertgoers onto a large LED screen placed on a spacious, raised stage behind Jay. He stood tall near centerfield, in dark shades with a custom Yankees fitted atop his newly shorn hair, wearing a white T-shirt, baggy seersucker pants over loosely-laced Timbs and a faux bulletproof vest. He examined his flock and threw up the Roc sign as “U Don’t Know” thunderously cut through the dry summer heat. Instantly, 45,000 fans each elevated their left and right hands together to form a diamond, returning the gesture. 

The more things change, the more Jay-Z tries to keep them the same. 

Jay’s performance was more than a trip down memory lane. It was as coordinated as Gerard’s dinner outfit in “Boomerang.” A muscular display of musical and technical ability mixed with a keen eye for messaging and positioning; think of Jay as Don Draper during the Carousel Pitch.   

That giant LED screen flashed images of impoverished life, Black joy and the Carter Family so predictably you’d swear you were watching a Hallmark movie. 

Today’s intentional is yesterday’s shrewd, after all, and the difference between the two is a few commas and some pesky paperwork your accountant has to file at the top of the year. 

This isn’t a pessimistic take, however. It’s an acknowledgment of his brilliance, with a (third) eye on the bullshit. Which, depending on your view, is how you see Jay-Z. Or, maybe, it can be both? #tension

Throughout a 30-plus year career, Jay-Z has transformed from a scrappy, lyrical rapper riding Jaz-O’s coattails to a dynamo the likes of which hip-hop has never seen and may never witness again. And he’s expanded his empire over and over again into fashion, spirits and technology. But the way it all works is by way of his music. 

Like the hustler he once was (still is?), he knows when the product dries up the corners go empty. And when bad product threatens his reputation, it’s back to the kitchen to whip up some new work. What better batch to serve up than a three-night blast of nostalgia? (It’s a twinge far more powerful that memory alone, natch.)

And he was in need of that raw. While he’s been lifted up in rarefied air by his day-one fans—who tolerated his occasional misgiving like displacing folks in Ft. Greene in favor of the Barclays Center, the Occupy Wall Street/Occupy All Streets T-shirt fiasco and saying "my presence is charity”—the younger generation didn’t get what all the fuss was about when it came to Jay-Z. His last solo album dropped 10 months after Colin Kaepernick first sat on the bench instead of standing for the National Anthem. And while the Black Lives Matter Movement got its start in the early Twenty-Tens, folks can have tunnel vision on the George Floyd protests and Covid lockdown years as its prime. It’s become a quagmire for Mr. Carter: what have you done for me (us) lately?

Jay, though, has a long memory. It’s why he’s so quick to get prickly at the piousness of Gen Z rather than explain himself. He backed Sean Bell’s family financially, put a spotlight on the murder of Trayvon Martin and led efforts toward community causes (pro Obama, anti LVMH).  

That’s why he shot back at his critics on Friday with a freestyle that centered Kaep and the Target boycott. His target was hypocrisy, of course, even if he sent out some friendly fire in the process. It was hardly a dis. But it also might not be what the times are calling for; there’s bigger issues facing our community than what a billionaire or retail giant is doing–and compassionate capitalism isn’t the answer to our needs, even if the intentions of an Obama, Oprah or Carter are behind it. 

So, what’s a GOAT to do? The thing he does best: sell himself. And not out, either; he brought some friends with him. 

Trunk (Music)

Music, news, reads, podcasts and videos that I’m checking for this week.

Feel like it’s too quiet around Future’s Real Me album. [Listen]

Tierra Whack should have made B.Dott’s midyear rapper list; her Whack Museum isn’t a Top 5 rap album, but she’s spitting high level raps and has earned her way into the conversation. [Listen]

High on my list of favorite songs this year, Coi Leray and Eladio Carrion’s “Outside.” [Listen]

My brother Bonsu Thompson edited J. Cole’s one-off magazine, The Fall-Off. Quality content. Cop one. [Info}

My man Carl Chery with an evolved look at Drake’s Iceman album. [Read]

Loved the Jay concert (if my essay didn’t address that, it’s more so because I wanted to wrestle with the view of what he’s doing and people are saying — but didn’t love the GQ interview; it’s solid, in a way, though. [Read] Related: Not looking forward to his Rick Rubin interview series. [Info]

Let’s Rap About It is my favorite podcast out right now now and it’s not even close. [Listen]

I got to work closely with Charlemagne on the day to day for 10 months when I ran The Breakfast Club on BET. He’s an earned thinker, who puts intention behind what he’s doing, even if you agree or not. This convo between him and Akademiks might not be your cup of tea, but it’s a fascinating exchange on where the media landscape is right now. [Watch]

Tyga, you got my attention with this synth, New Wave sound. [Watch]

Lil Tjay and The Kid Mero? A Bronx kid’s dream. [Watch]

Backseat Freestyle is written and produced by me, Jayson Rodriguez, impartially and independently via my company, Smarty Art. If you have any comments, feedback or questions, feel free to email me: [email protected]. If you would like to discuss sponsoring an issue of the newsletter, contact: [email protected] and check out the rates, here. And follow me elsewhere:

Instagram: @jaysonrodriguez

Since Jay-Z weekend is rooted in the choice between Reasonable Doubt on Friday or Blueprint on Saturday, what say you? Which is the best out of the two?

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