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Wale and Jerry Seinfeld

David Sherry
4 min read

I totally missed it.

Back in 2015, Wale, a D.C. rapper and Jerry Seinfeld put together a record.

How does something like this even come together?

“So I had heard his name and then he came to a show and asked if he could say hello, so he came backstage. I thought he was a very charming young man. And then I heard about the mixtape, and he came up with the idea of doing the whole album. It just felt so offbeat and that’s what appeals to me.” - Seinfeld

I’m a huge Jerry Seinfeld fan. I’ve seen all of the interviews but this record slipped through the cracks.

Jerry is a sucker for the offbeat. It’s why he did the Bee movie, a kids movie with adult humor. When you hear him interviewed, he's got equal part lessons and equal part mystery. That's the thing about Seinfeld, it's like he barely talks. He scrapes the surface with everyone and it bothers you because you want to know more about what's really going on under the hood.

It bothers you because he seems to be totally OK in a world of comics who are typically needy for attention and troubled (which makes their art, great).

I suppose only Chris Rock and Dave Chappelle have landed in this place, at least later in life where it seems like they can just be themselves.

If you want to dive in, there are classic interviews on Stern back from when his show was a hit. There's some behind the scenes on the set interviews of him and Larry David. And, a more inspective view when he goes on Alec Baldwin's "Here's the Thing" and the most you get out of him is that he's content.

So he's part lessons part mystery.

Or maybe it's that the lesson is that there is no mystery to his work, he just works at it.

But what's incredible about Seinfeld is the trajectory of his career.

He creates the greatest show o all time, and then follows it not by taking over the world, not by cashing in like the Marvel series with unlimited budget pumping out show after show...

Instead, he waits. He's comfortable with that one hit.

Then he bides his time and then he strikes when he sees an opportunity. But he knows that he'll never hit mass appeal again. So instead he seeks out the weird, and the interesting, the new and different.

He meets Wale. And Wale has a concept for an album the relates to the show. "The Album About Nothing"

And like his other moves, the masses miss it.

Comedians in Cars Getting Coffee was turned down by every online presence except theunknown “Crackle Media” which effectively died after they couldn’t continue to pay for the rights. But now you can view CICGC on Netflix.

It's always about your latest hit. And apparently, even Netflix and Amazon didn't believe he could produce again.

But back to the album, and to Wale.

I learned this bit of Jerry trivia because of Wale's interview on Pete Holmes "You Made it Weird." It's a comedic show with a bent towards the bigger questions in life like religion, with guests ranging from Rob Bell and Aaron Rogers. And sometimes you love Pete for his joy and sense of humor and sometimes he talks too much over the guest...

But on the show Wale is refreshing.

He sees between the lines of old school hip hop culture and the new breed of rappers. Jay Z, Snoop, Dre and all the others lived the gangster life on the streets and rapped about it because it was their life!

Rappers today talk about drugs and guns but it’s more a metaphor for the culture, for the history, and it's not always from real experience. There's a divide between the old-school rappers and the new school. But the topics are the same, it's just the worlds are different.Except for possibly drugs which are prevalent everywhere.

The name of the game for hip-hop is collaboration. So maybe it's only natural that Wale is open to all and any collaborators, even Jerry Seinfeld.

What’s appealing about Wale is his earnest perspective, matched with a focus, which comes from his internal struggle of fearing failure.

Jerry is about the cash. He leverages art that’s working for top dollar. He’ll do the club for free to polish his skills, but when he’s got something to sell that he believes in, he goes for asking for as much as he can. It's unclear what his monetary role was here.

But you put them together, and you bridge communities by uniting around a show that everyone can love, Seinfeld. That's the idea anyway.

It hit #1, but I'm not sure the culture can sync up with something like this anymore.

Which is why this can go right on by without notice.

And I admit, personally after a few's not quite there for me. I prefer his 2011 Album "Ambition" produced by Rick Ross. His happy/pop style upbeat album.

But the point is Wale and Jerry tried something new.

Something worth talking about. They knew it wouldn't be for everyone and it's this type of artistry that's needed to break outside the noise and gather interest.

We want something fresh.
Doing that means taking a risks. Likely, it won't work. But just maybe...

So, you keep putting out product.

This is the mixtape ethos.

You keep putting out product.

xx David