When XXL dropped its 2025 Freshman Class of emerging hip-hop talent earlier this week, the comments section seemed divided over this year’s selection of rappers. However, the consensus among many seemed to be one key notable missing face, ascendant Chicago rapper Chuckyy.

At just 19 years old, the Lil Durk protégé is pioneering his own distinct drill sound. With hints of horror-core and a refreshing nonchalance, the rising young rapper represents the new era of Chicago rap, also working closely with the city’s local legend LUCKI.

Fresh off his I Live, I Die, I Live Again release and a recent performance at Lyrical Lemonade’s Summer Smash, the rapper is already ready for his new move: a tour, a deluxe edition, and, hopefully, becoming the richest rapper in the world. But first, Chuckyy pulled up to Chinatown for a quick chat about his Chi-town come-up.

Your latest project has been very well-received. Do you pay attention to the reviews and ratings?

I feel very blessed about that. I try not to read the reviews too much, but I appreciate every single person who has poured one out to the album or supported it in any way.

Where did the album title come from?

It’s one of my favorite lines, and I think it really emulates the journey of this album and the different stages of life I’ve been going through. You go up, you go down, but you keep going.

What about the cover art?

The poses are inspired by Chucky on the cover art.

What were some of the biggest sources of inspiration for you on this album?

For this album especially, the fans have been the inspiration. I’ve been really active with them lately and have been trying to actually listen to what they want from my music.

What does it mean to work with a legend in your city like LUCKI?

I’ve been listening to LUCKI forever, long before I was even rapping. It’s so crazy to get to call him a peer of mine and get to rap together on one of my own tracks. That was the last thing on my checklist, for real. Now I’m done. Now I can really have fun. Shoutout Luck.

Lil Durk is another mentor of yours. Tell me more about his influence on you.

He’s such an inspiration to me. To see someone from the same place as me be able to achieve such big things – it’s so motivational. It’s helped me so much.

You’re just 19 – do you ever feel like you’re moving too fast?

No sir. I don’t think I’m missing out on being a 19-year-old. I don’t think I’m growing up too fast. I don’t think I’m living too fast.

How do you approach writing songs?

All my tracks come together from scratch. My engineer and I are locked in, and he’ll make a beat, send it over, and I’ll just hop on it. I’m going to record a song after this interview. I actually sat down and wrote it before. That’s crazy. I haven’t done that in so long.

What’s next for you?

A tour is definitely on my mind. Also, a lot of music. I’m not about cliffhangers. Everything they see is going to drop.

If you could collaborate with anyone, who would it be?

Lil Uzi Vert.

What’s your most underrated song?

It’s called “King Tut.” It’s from when I just started rapping. It still doesn’t have a million views.

You’ve debuted on Billboard, broken millions of streams – what’s your “I made it” moment?

When I’m the richest rapper alive.