How Digital Natives Are Making Hip-Hop Great Again

The following post is an experiment. An old friend asked me to make him a playlist to catch him up on what he’s been missing in the hip-hop world over the past several years. I’m sharing the list and commentary as an essay of sorts. There’s more here to be explored later too, but normally this would have been a private exchange. The iTunes link to the playlist is and the Spotify link is (h/t Ryan) Anyway, enjoy.

First, here’s the list: 38 tracks, mixtape rules apply (yes, it’s in a specific order, no you shouldn’t shuffle or hunt until you’ve worked through it). These were selected from playlists I’ve made for myself over the past few years, with your request to “catch up” on what’s been interesting in hip-hop in mind. In other words, this is not a complete list, but it is all mostly new(er) music that I personally enjoy. In a weird way, it probably is picking up close enough to where the last mix I would have likely given you trailed off (early/mid 2000s?). I started to put my head in the sand around that time and then streaming subscriptions saved the day for me personally. More on all of that in the digital liner notes below. Full warning, a short rant to give you context turned into one of those BlueNote album cover article/essays.

1. Say I didn’t by Vic Mensa

2. Hazeus View by Joey Bada$$

3. Actin Crazy by Action Bronson

4. The Full Retard by El-p

5. 36” Chain by Run the Jewels

6. Yeah Right by Vince Staples

7. Big Bank (feat. T.I.) by Big K.R.I.T.

8. Smile by Jay-Z

9. Ultralight Beam by Kanye West

10. Blessings by Chance the Rapper

11. Raise Hell (feat. Killer Mike) by Sir the Baptist

12. We the People by A Tribe Called Quest

13. Come Down (feat. T.I.) by Anderson .Paak

14. i by Kendrick Lamar (the non-album, single version! Do NOT get the “To Pimp a Butterfly version, more on this in the notes)

15. Phantom (redux) by Shirt

16. Quiet Dog by Mos Def

17. Girls @ (feat. Chance the Rapper) by Joey Purp

18. Caroline by Amine

19. HennyNhoes (feat. Christon Dior) by Young M.A.

20. Truth Hurts by Lizzo

21. Bills by LunchMoney Lewis

22. Ain’t That Easy by D’Angelo and the Vanguard

23. Location by Khalid

24. Drew Barrymore by SZA

25. Girls (feat. Horsehead) by Lil Peep

26. Wufi by Jayy Grams

27. L.A. by Murs and 9th Wonder

28. Huzzah by mr MFN eXquire

29. Smokin and Drinkin by Danny Brown

30. Bumper by P.O.S.

31. Oh My Darling Don’t Cry by Run the Jewels

32. DNA. By Kendrick Lamar

33. R.A.P. Music by Killer Mike

34. Pyramids by Common

35. Go Tell’em by Vic Mensa

36. Worship by Lizzo

37. Southern Belle by Sir the Baptist

38. Sunday Candy by Donnie Trumpet & the Social Experiment

So here’s what I want you to know about this that we can’t exactly talk about over breakfast at Captain Al’s (RIP).

The kids making this music are different from every prior generation and you should be excited. They aren’t constrained by the local radio station, or record store, or even what’s on MTV. The internet cracked everything open, and if you’re a digital native (they say born in 1996 on, but I’d generalized to 90s on), you were born unconstrained.

Art has always existed across borders and mediums, but social media and how digital natives experience being music nerds makes this actually a new-new thing. Hip-hop in particular was built for social media. DJing, rapping, breaking, graffiti – those 4 elements KRS was educating us about, they are nothing that an Instagram post or Snap can’t capture. The 4 elements are just playing music, saying something, dancing, and/or art/fashion. I’m not saying that rock doesn’t have similar attributes, but hip-hop was already subdivided up for social media adoption.

While we toiled away earning our geek-cred the hard way, digital natives were born googling it. Think how much faster you would have traced influences and discovered things you never would have imagined you’d like. For example, consider this chain: Nirvana biting the Pixies’ loud-soft-loud, the Pixies loving the Velvet Underground, the Velvet’s Andy Warhol connection – you know what it felt like to follow that one thread all the way through the proverbial sweater. Imagine that amplified with google-fu.

This means today’s geeks fall down the rabbit hold that much faster, and that much deeper. And the super-geeks who actually feel the NEED to create new music too? It’s like they have superpowers and MBAs in some of this stuff. And, because they’re still young, sometimes they don’t even know why Nirvana or Biggie or whatever clicked with them – it’s this primal association that’s driving these connections. Come on, you’ve got to be excited with me by now.

Anyway, here are a few highlights as you dig in:

At the bookends you have the city of Chicago. Between the corruption, the murder rate, the violence, the inequality – Chicago is messed up right now. Maybe because of the internet, maybe not – there’s not a wall of oppression that is causing the next NWA to pop up here (well, Chief Keef aside). Instead, we’re getting soul and gospel samples, stories that include relationships between multiple generations of families, respect for the concept of church, the (re)definition of social salvation and redemption. Vic Mensa told you he was going to pull this whole thing off, didn’t he?  Talk about uplifting. And Chance, he’s distilling the world down into the Sunday candy dish at his grandmother’s. Darkness isn’t going to win.

Probably the oldest track here is “Quiet Dog” by Mos Def. I think this was out in around 2011. It starts with a Fela Kuti sample describing how he’s not changing, and his views on politics are getting better and smarter and stronger (paraphrasing, of course). The song then kicks off with Sugar Hill lyrics. Digest this much with me for a second: an extra-literate rapper from the 90s is aging and still involved in hip-hop. Like Fela, the original allure is still there (remember, Fela wrote live songs before he got political), and now he’s evolving as a person too. Mos wants to get that on the table – artist evolution – and then take you straight back to the beginning, hence the “Rapper’s Delight” quote that he opens with. What follows is his critique of the state of the industry, some cautioning about rap being too much about flash and how “loud” you can be, and the hook being a subtle reminder that the “quiet dog, bite hard, my god.” If, “preservation made the greatest hip-hop,” then Mos says to take care of those core elements and without being stuck in the past, “preserve the rock, don’t stop the rock.” It’s not whiney-old-guy-left-out stuff (ahem, Walk Om Water, I’m looking at you), it’s relevant criticism across generational lines.

The other elder-statesmen you already know are here too. Jay-Z gets introspective about his mother. Kanye basically produces an incredible musical vibe and puts Chance in the spotlight. Tribe gives us one last gem before Phife passed. EL-P is like a modern Johnny Rotten, you’re just not going to get something that isn’t coming at your neck with a broken bottle. Teamed up with Killer Mike as RTJ, you don’t need them for introspection. If Mos Def wants the kids to simmer down, they’re still proudly rocking 36” chains and jacking poseurs.

Kendrick Lamar is king and you’ll find plenty of him here. Just to whet your appetite, here’s some background on “i.” The song gets released as the single for the then upcoming, and highly anticipated, “To Pimp a Butterfly.” The cover of the single features Bloods and Crips making heart signs with their hands. You know the sample straight away as “That Lady” by the Isley Brothers. With just that much information, we can start dissecting (and this is why he’s king).

The title is lowercase because he’s deemphasizing “I” as in “self.” The Bloods and Crips making hearts are doing the same thing visually – abandoning the gang signs for a different, idealized version of self-definition. Remember, in a world of social media, accompanying visuals are more important than ever (even if most people don’t notice them at this level). “That Lady” is about the mysterious magnetism of a strong, black woman, but here Kendrick’s chorus is “And (I love myself) / when you lookin’ at me, tell me what do you see.” He’s trading the object of affection from romanticizing an external ideal to considering an internal ideal (“heart” and how it takes a deemphasis of ego to overcome a culture of violence). The song is about his own evolution from gang culture to being a self-aware voice. From the power of I to the power of i. It’s triumphant. It’s stoic.

Then, when the album comes out, there’s a different version from the single on the album itself. Not a remix, not an extended cut, but a live version that cuts off halfway through because there’s a fight in the audience. Without taking you all the way down this rabbit hole, Kendrick has primed you with the single, prior to the album, only to surprise you with a twist on the album, AND he manages to fit the entire thing into a broader narrative arc about the agony of translating the message and communicating it back to his community – you know the ones who get into a fight during his song’s performance?! It’s still a struggle, and he’s contextualizing it in multiple ways, on multiple levels, through visuals, samples, lyrics – he’s the king right now.

Last point to make – then I’ll let you figure the rest out for yourself – there’s some R&B mixed in here too. Khalid, SZA, and even the late Lil Peep doing some singing that might not make complete sense at first. Go back to the idea of the internet and social media having changed everything. Think about Marvin Gaye’s “What’s Going On.” Think about how he frames the world through the eyes of a soldier coming back home to the people he’s been fighting for and what the struggle is like. There’s no war in Khalid/SZA/Peep’s world, but there is a new form of romantic relationships they’re struggling to define.

Those of us born before 1996 definitely don’t understand what it means for our entire lives to be on social media. To manage that external brand of who we are and find truth/love with another person, that’s a new teenage war. From self-esteem, to drugs, to finding the “location” where we can actually meet in reality, or wondering if we’re “warm enough” to be accepted and loved, this is WAY past some Dark Mirror science fiction.

I’ll let you discover the rest and look forward to breaking some more of this down together. Anything that makes you scratch your head, just remember the framing of where these artists are coming from technologically. The bars, the hooks, the swagger, it’s all still here, per Mos’ hope.  The future looks bright, and this is a golden age indeed. The digital natives are making hip-hop great again. From one old dog to another, look on approvingly. If asked, just tell them, “simmer down. Quiet dog, bite hard, my god.”