You might know him from the recent Slow Pulp show at Lincoln Hall. Or maybe you’ve been around since his fear itself. days. Personally, I first saw Chicago-based rapper CRASHprez live in Madison, WI a few months ago. I was there to see Jackie Hayes play, and toward the end of the set, CRASHprez cannonballed on stage to deliver a raucous rendition of the second verse in “Focus.” I saw him perform again at Lincoln Hall, where he set the crowd ablaze with his forthcoming single, “SASSMAN.” His electric stage presence and ability to command an audience of Midwestern indie rock kids astounded me. 

Michael Penn II is the mastermind behind CRASHprez and one-third of defprez, a hip-hop supergroup composed of Penn, knowsthetime (Ian Carroll), and Defcee (Adam Levin). Raised in Maryland, Penn cut his teeth in Madison, where he brushed rap royalty with the likes of Vince Staples and Chance the Rapper. And though he’s only lived in Chicago for a few years, Penn has quickly become a local mainstay. In anticipation of his upcoming single and defprez’s new album, It's Always a Time Like This, we sat down with Penn to talk about his recent merch drop, releasing new music, collaborating with other artists, and much in between.

Can you give me a brief history of how you started making music? 

So I'm from Maryland—people think I'm from Wisconsin, but I'm not. I started making music at the end of middle school and was releasing it on the internet. I had a home studio set up and put my first tape out when I was 15. It's been over a decade, which is ridiculous. But yeah, then I ended up getting into First Wave, a program at UW-Madison for people in hip-hop. I went to the Journalism School, but I was also making a lot of music and opening for everybody under the sun in that four-year period.

That's when I put out fear itself. and more perfect. I really cut my teeth in Madison and I met motherfuckers before they blew up. It was a certain period of Midwestern music that people associate with the blog scene, like that mid-2010s era.

Who were some of the artists you met?

Saba is a person that comes to mind. I opened for Vince Staples at one point. Psymun, the producer from Minneapolis, that’s my dog. Groupthink was in the same program as me, so that's how we met. KennyHoopla was in Madison for a brief period, like 2015/2016 or so. I opened for Turquoise Jeep—it was very weird because they gave me a whole hour. Chance the Rapper at one point, Danny Brown. Defcee and knowsthetime, who're in defprez with me, were two of the first artists I met when I moved to Madison. It's just a lot of people.

So how did you end up in Chicago? 

It was a natural progression of things. I graduated in 2015 and chilled in Madison for a little bit. You know, everyone's like “Go to college, go to college, go to college, go to college, go to college.” You do that and then you're like, “now what?” I just kinda sat around and then after a year moved to Minneapolis. A lot of people that I looked up to when I was younger are from there, and a lot of people I ended up cool with are from Minneapolis, like Shrimpnose, Psymun and K.Raydio.

It's a deeply-underrated music city. I played a show with Dua [Saleh] before they pop popped. That whole scene is nuts. I was just really attracted to the energy of what was coming outta there and I wanted to pull up for a second. That did not work for me. I got outta there. One of the first shows I did out there, one of the older homies pulled me to the side and said “You from here?” I'm like, “Nah.” He said, “What'd you come up here to do?” I said, “Do music.” He's like, “Leave. It's not it. Leave. Leave.”

I moved back to Madison and I was also freelancing heavily at the time, doing a lot of journalism. I wasn't on staff yet, but I was freelancing for Vinyl Me Please and I had clips in Vice and shit like that. And a bunch of local stuff through this blog called Tone Madison. I got hired at Vinyl Me Please in 2018 and then I moved to Chicago in 2019. I was barely in Chicago before COVID sat everyone down. And here we are.

How did COVID affect your career?

Niggas was depressed. Niggas is depressed. I put a project out right before COVID with knowsthetime called I’ma Die Anyway. And I was about to go to South By [Southwest] for my old job at Vinyl Me Please. And then that did not happen. None of it happened. Everyone got sent inside and it was like “Uh, we're doing shows on Instagram now, I guess.”

Did you write a lot during that period? 

It was sporadic, but I will say the defprez album started out of that. I recorded a lot in summer 2020--even stuff I haven't put out yet. I was going to Classick a lot, we was working for real. But I wasn't really releasing anything cause everyone was terrified.

You saw how quickly the industry crumples in on itself when nobody is making money without touring. It gets really shaky and people do whatever to keep attention on them and to try to get that money. Cause this whole thing is rigged against the people who actually put life and blood into it. I can't go to shows. I can't play shows. I can't do nothing.

I covered the drive-in Lil Yachty concert. It was one of the funniest things. Everybody's at their cars and nobody can mosh pit or be around each other. It was weird and awkward.

So, tell me about the new defprez album. 

So defprez, as far as being a group, wasn't planned. Now Ian's in New York and Adam is here. But we started in Madison. We made three songs in a weekend and put them on SoundCloud, and it just became what it is. So defprez is a group of people that I've known for a decade. I guess it's a natural progression of our friendship. These are like my brothers for real. We all just love rap, we love supporting each other. And for the album itself, the through-line is pain, trauma, growing from it, and rising past it. The album's called It’s Always a Time Like This, and it's 10 songs. It's part origin story, part we just rapping, part we're surviving the whole thing. It's very brief but it's very heavy. And it's odd to think we started right before lockdown. It's taken some time to get it out of the gate. It's like a time capsule, hearing how I was feeling two, three years ago. You listen to it now and a lot of the emotions and feelings still feel current too.

And CRASHprez has a single coming out, right?

Yeah, “SASSMAN.” I played it live three times now. People react really crazy to it. All people talk about is the beat drop. Ian made the beat, and it's funny, because he doesn't know what the hell to make for me. I'm impossible to make beats for ‘cause my taste is all over the place. So for this new single, Ian sent this beat that I didn't see for myself. He sent it to apparently everybody, and everybody flaked on it. So I had to come back around to hear it again. I'm like “Bro, nah, I was wrong. Let me try that.” I don't know if it's indicative of all the stuff I'm doing moving forward, but I think it's definitely a clue as to where I'm headed sonically. Regardless of me playing with more of a guitar sound, acoustic type shit, me trying to figure out what my singing voice sounds like, me trying to get deeper into songwriting, no matter what era I'm in or what time I'm in, I'm always gonna try to have some shit that goes crazy. The song kinda outlines my history, bouncing around.

It’s pretty obvious that a lot of your music is political. What do you think music and art's role in protest is?

I can't speak on that. I don't know. I think that's everybody's question to answer for themselves. I don't know how to be prescriptive because I can't occupy everybody's worldview.

What does it mean for you then? 

Everything's political. Everything's a choice. I try not to preach. Instead, I try to show people where I'm at based on where everybody else is at. I feel like a lot of my early music was kinda pointing at shit, but I'm not as interested in that anymore. I'm not here to point to this shit and just make statements, but I'm always gonna speak on what's important to me. And I'm gonna have it be genuine. I don't want my music to sound like thinkpieces. If you listen to my music for real, you're gonna hear where I'm at and where I stand. You're gonna hear that gay shit. You're gonna hear that Black shit.

People will deadass hear a whole set of mine and not even clock that I'm rapping about gay-ass shit because they don't be listening to these words. Is it their fault? Is it my fault? Is it anybody's fault? I don't know. But if you listening to me and you really like that rap, for real, you gonna hear what I stand on. And if you stand on that, come with me. I may not be the guy for everybody, but come give it a try. ‘Cause I got a lot to offer.

I'm saying like nothing makes sense. Time's getting more and more incoherent. This world makes no sense. It's kind of falling apart and niggas are still dancing through that shit. My music sounds like that.

Some of my friends can play guitar and I'm gonna sing on that too. But at the end of the day, I'm a rapper. Rap that's more political, more explicitly outlined—I'm cut from that cloth. That's what I came up on.

Speaking of genre-melding, I know that you co-wrote a lot of Jackie Hayes songs on her latest record. I'm curious how that came about and what it was like to work on a record that's seemingly so different from what you've put out. 

Working with Jackie was the first time I got to work extensively with another artist. We had to learn each other for real. I'm over here throwing shit in the Google Doc, but with her, that's not gonna click because her approach is not my approach. What works in my world don't necessarily translate. There's way more brevity to her music. It's shorter; it's more concise. I had to learn what words she likes and how they sound. That really made me a better writer because I be thinking way more about how words sound together.

We worked on her EP There's Always Going to Be Something, so by the time we got to Over and Over, we had been collaborating for years. Our neighborhoods were right next to each other and we’d write in her home studio. I began to understand how the Jackie world works, what she probably would say or sound like. And to be clear, the bulk of that record is her. She brings me in to assist. And I'm really proud of being a part of somebody else's work like that. I'm really proud of that album and I feel like people are gonna give her love at some point in time. I don't know when, but even if it don't pop right now, I feel like that's the sort of record people will come back to and be like, “his was raw.” She is phenomenal. She's so special and she's really busting her ass for this. I respect her a lot. 

I saw you just dropped new merch. What are the ideas behind it? 

I never had a T-shirt before, but Ian was like, “Merch is how you make money in music.” It's very hard for me to articulate things visually sometimes, especially when it comes to things that people walk around in. Even when I got the first shirt, I was weirded out by looking at my face on them. I didn't want my merch to be like a band shirt you buy that you don't wear nowhere but the house or on an errand. I want people to be able to rock it; I wanted it to look raw. Literally the picture is my passport picture. Literally. I like the way that looks. I got the picture during COVID. And the shirt is all Ian's design—he took all my ideas and turned them into this streetwear thing.

A lot of it is inside jokes for me. So first of all, I should have did this t-shirt a long time ago. Here it says "Michael Penn II is my favorite friend," scratched out. Post Malone really said that to me on Twitter. We argued on Twitter for like 20 minutes because I wrote an article about him having white dreads, like “Why you acting like a nigga?” basically. All the tweets are gone, but I have them. It's part of my Michael Penn lore, I guess.

Live from the Four, the Four is Fort Washington [Maryland]. That's what me and my niggas call it. And then, I really wanted to have a shirt that says “I listen to CRASHprez. I'm an ally, I swear.” Ian thought it was hilarious but said no one would ever wear that. So it just says “I'm an ally, I swear.” I'm an Aquarius, so it says that. And under it are some of the ways—ain't even all the ways—that people spell my name wrong. Everybody thinks I'm saying “Cash.” How do you get that?

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