Jay Wood first caught our attention about five years ago through a run of impressive singles. As his catalog grew, overtones emerged: shamelessly honest writing, triumphant production, tasteful features and visuals that expanded the world of each release.

In 2023, between directing his first documentary and releasing his debut project NOWHERE, FAST, Jay landed on our Chicago Artists to Watch list. Since then, he’s continued to raise the bar by consistently showing both the capacity and ambition to create some of the most intentional, high-quality work coming out of the city.

That evolution is evident on his first full-length independent LP, PARADISE DON’T LAST FOREVER - a super personal body of work that leans into reflection, restraint & emotional clarity. Now, we take time to talk with Jay about this defining chapter of his creative career and the path that led him here.

Thank you for taking the time to chat with us Jay, how has this year been for you?

Man it’s been a crazy year. It flew by too. But I did everything I set out to do.

We last caught up with you in 2023, both as part of our Chicago Artists to Watch series as well as surrounding the release of your documentary HOMESICK. When you think about your growth as an artist from that point, what comes to mind?

I feel like I always had the vision, but this go-round and this rollout to me feels evolved. More mature, sharper, more honest. I think I’m more sure of myself than I’ve ever been.

This year you released a really special project in PARADISE DON’T LAST FOREVER, talk to us a bit about the making of that project…

I was traveling back and forth to Florida to take care of my OG. That experience alone inspired the title. When I was home, I had a lockout at the crib with the homies and made the whole joint in like a week, maybe two. We had a lot of fun.

“DRAMATIC” is one of our favorite songs to come out of the city this year, what can you share with us about that one?

Banger. “Dramatic” started out as an interlude with Quintin and me. Side note, Quintin has been a collaborator of mine since we were kids, if you do the homework you’ll see his name. But yeah, the song started as an interlude. I played the keys and had these mallets. I was in LA for a little while and linked with Jonah Renna. Crazy talented. We took that interlude and turned it into a whole new track, with drums and a new verse. We were in the flow state for real. I think I’m going to find something cool to do with that song.

As long as we’ve followed you, your visuals have always been extremely tasteful and well done. Can you speak on how you approach those?

Honestly, it’s probably a nod to my degree and what I studied in school (digital storytelling), but I’ve always been a fan of good cinema and intentional storytelling. Whether it’s through albums, movies, television, etc. For this project specifically, I had an “album booklet “ where I laid out my vision. Planning something cool with that booklet, too.

Who are a few of the creative collaborators that have helped you bring your sonic & visual worlds to life?

So glad you asked because they need their shine. Visually, Law and Ambercita have moved mountains for me. They both are extremely talented and genuinely believe in my vision. They make me look good. Sonically, Tupni has been my engineer for about 2-3 years now. He be glassing shit. A good mix can take a good song to great, and he understands what I'm tryna do with my voice / beat selection, etc. S/O my nigga tup. Gotta shout the home team one time, namesake, Moses, and Wanya . As I’ve stepped into a role of leading my production and self-producing most of my songs, these guys are still my cheat codes. If I send them an idea, they’ll send me back a song. SOS and Chen have been great help with vocal production, and background vocals, and all that too. Can’t wait for y'all to hear more from them, they got some SHIT.

When you’re not listening to your music, who are a few of the artists you have in rotation consistently?

It’s hard to say, but I really enjoy listening to neo-soul and that soulful R&B era of the 70s and 80s. As far as more recent drops Lekan and Natanya been on repeat.

What’s the best way for the These Days audience to follow along & support your music moving forward?

Hit me on the gram, man @jaywoodsole. That’s really HQ. I’m everywhere, though.

Any final thoughts you’d like to share?

Man, shout out to y'all for being this pillar of community for the crib. It’s been a great ride.

Jay Wood is Passing Through Paradise