"Diamonds & Wood" is an ongoing series in which music critic Shea Serrano breaks down the 5 hip-hop tracks you need to hear this week.

My main homeboy right now is a 60+ year-old-man.

His name is Kevin, except his name is really K-Yo, except I mean his name is really “Kaaayyyy-YO!” because that’s how I say it every time I see him. (His response every time: “Hello.”) He lives just a few minutes from me and he teaches at the same school and we ride together to and from work, so that’s how that is.

At the moment, he’s definitely one of my four favorite people. He’s not necessarily a hardened man—like, I mean, life hasn’t beaten him into an impenetrable shell—but, given the option, he would mostly choose to keep to himself, I’d guess. (This is a trait that I possess too, which is part of the reason we get along so well, I suspect.)

When he drives (he always drives), he has a tiny pillow that he places between the door and his knee for comfort. He wears big Blublockers sunglasses over his regular eyeglasses because the sun is bright. He has a flip phone and he uses it every morning during the work week to call me at 5:55 a.m. to tell me he’s about to leave his house to come get me. We don’t have to be at work until 7:35.

Were you to just look at him (which is basically how you should judge everyone, Twitter told me), you’d have no idea all of the wonderful things rattling around in his cranium. He has a longLongLONG, unkempt beard and his shoulders are hunched just a tad so his head is pushed forwards and slightly downwards. The edges of his mouth point downwards. And he does walk, but it’s only barely that—generally, he just glides places, like a specter with its ankles stuck in the terra firma. I’m not certain he’s ever actually removed his feet from the ground.

But Kaaayyyy-YO! is atypical. He is a treasure trove of insight and knowledge. (I first figured this may be the case in 2012, when I saw him play the harmonica at our school’s talent show. He was AMAZING.) One day while riding home, we listened to a Louis C.K. comedy routine. When it finished, he mentioned to me that he was a standup comedian 30 or so years ago, and that he actually had old cassettes of his performance at his house. I begged him to bring them for our ride until he finally did. We listened to a 20 minute bit that ended with him in a raft throwing pigs into a boat. I loved it.

A separate time he showed up with recorded tapes of himself and his buddies making music and jokes.

A separate separate time he told me about all of the jobs he had before he was a teacher (one included a gigantic computer the size of a hallway and a machine that required him to read addresses and input zip codes one per second for hours straight).

A separate separate separate time he explained to me how organized sports were a joke, that they represented something baseless and something something something*

*I’m probably at least a little bit smart, but Kaaayyyy-YO! is for real smart. Sometimes he says so much stuff that it gets jumbled in my brain. I feel the same way when he really gets to spouting vocabulary the same way I did in college during Philosophy of Science class. I’m shaking my head like, “Right, for sure, definitely,” but in my brain I’m like, “WHAT THE FUCK IS HAPPENING RIGHT NOW ARE WE EVEN STILL SPEAKING ENGLISH I WONDER IF HE’D NOTICE IF I CLIMBED INTO THE BACKSEAT AND STARTED CRYING FROM MY OWN DUMBNESS.”

But where Kaaayyyy-YO! is really great—at least for me, anyway—is when he gets to discussing music. His collection of older rock is impressive and each day he has two or three new CDs for us to listen to, each time providing commentary. (“Americana merged numerous genres, and is at its best when the singer fully believes in the American musical ethos he or she is singing about”; “This era of blues really strayed from the traditional Western diatonic scale”; “The first time the Ramones played was 1974 at Performance studios." Things like that).

I don’t have any grandparents left. Maybe that’s part of the reason I enjoy Kaaayyyy-YO!’s rickety presence so much. Or maybe it’s because I see quite a bit of myself in his beard. Or maybe it’s because he effortlessly says things about music that I’m incapable of explaining to anymore without .gifs and YouTube links.

I don’t know.

But yay, old people! Here are some YouTube links.

1. Roosh Williams, “The Introduction”

Roosh Williams has been piddling around WAY far underground for a mixtape or two now. This is the best thing he’s ever made. The first 40 seconds are just about wonderful.

2. Chance the Rapper, “Juice”

I’d not heard of this guy until the above video was passed along by the boss. <3

3. King Louie, “V-13,” featuring Yella

Just as a general rule, you should go ahead and love any song that sounds like something that gets played right before a maniac bludgeons a co-ed over the head.

4. Kid Cudi, “Immortal”

I’ll never understand what happened with Cudi. His A Kid Named Cudi mixtape thing was fantastic. So was his first proper album. After that, he just disappeared. I’m glad he’s back. Always root for the skinny guys.

5. Lil Poopy, ALL THE SONGS

Srsly, chillbros?

Shea Serrano is a writer living in Houston, TX. His work has appeared in the Houston Press, LA Weekly, Village Voice, XXL, The Source, Grantland and more. You can follow him on Twitter here.