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Conway the Machine in an orange jacket leaning against a truck. Won't He Do It press photo.
Photo by Henry Jones II.

Conway The Machine is Out of the Darkness on ‘WON'T HE DO IT’

Conway The Machine spoke to Okayplayer about his new album, WON'T HE DO IT, tension inside of Griselda, and more.

Conway The Machine’s impact on rap has become undeniable. Alongside his Griselda brethren, Westside Gunn and Benny The Butcher, the trio spent the 2010s chiseling away at the rap game, drenching the market with dozens of projects in the hopes of shaping it in their grimy, glacial image. But by 2020, their plan had worked maybe a little too well. Conway, in particular, had become known for his menacing delivery and ominous bars. His struggle with Bell’s palsy, resulting from an attempted assassination in 2012, had given him an abundance of street credibility, all of which he used to help him concoct a tyrannizing persona on the microphone. However, the boom-bap bravado of Griselda had birthed numerous copycats, and Conway admits that after dropping off his Shady Records debut,God Don’t Make Mistakes the doppelgänger’s finally got to him.

“The rap shit was kinda boring to me,” Conway told me in an office building above Times Square, surrounded by many of his latest Drumwork signees. “I feel like everybody was replicating what we’d been bringing to the game the last few years and it started to feel oversaturated with the same type of beats and content from these artists. I was looking at it like, ‘alright then let me do something else.’”

So Conway diverted his attention away from rap and decided to dip into his “CEO bag,” which was not something he ever saw himself doing. By 2022, he’d made Drumwork a full-functional machine with a stacked roster, and he was hard at work on crafting his own music festival with a little help from JAY-Z.

“I really wanted to be a Rakim or Slick Rick,” Conway said. “I just wanted to be an ill MC and do my thing and I was just focused on me so much, but now I just see this as another challenge. It’s like Jordan when he came back. My challenge is to 3 peat again. Like can I take this Drumwork shit from nothing to everything?”

Watching Drumwork come to life also inspired him to get back in the studio. So he flew out to Denver, Colorado, where he said he recorded six albums worth of music before putting together Side A of his latest effort Won’t He Do It. Creatively, the project finds Conway fully outside of his comfort zone, with his usual batch of grainy loopings substituted for opulent horns and soaring orchestral compositions. While God Don’t Make Mistakes found Conway reminiscing on past troubles, Won’t He Do It finds him merely indulging in the spoils of fame.

“I just wanted to feel like I ain’t have no limitations on me,” Conway said. “I just was in a good space thinking about how blessed I am, and I was like ‘won’t he do it?’ and I just kept saying that every time I heard a record. I always wanted to be hella versatile. So this is me in my versatile bag.”

Conway the Machine smoking a blunt in a room with red walls. Won't He Do It press photo. Photo by Henry Jones II.

OkayPlayer spoke with Conway about the new album, tension inside of Griselda, and more. The interview below has been edited and condensed for clarity.

Right out the gates, I wanna talk about songs like “The Chosen” and “Monogram.” Those beats are incredibly cinematic. When you wrapped on God Don’t Make Mistakes, how were you approaching the beat selection for this record differently than on past records?

Conway The Machine: I’d been working on God Don’t Make Mistakes since I signed to Shady in 2017, and I just wanted to tell my story. That energy for that album was full transparency and I wanted to give my story to people so they could have something to be inspired by and motivated by. But with Won’t He Do It I wanted it to be the total opposite. I didn’t wanna get too deep into the pain of the songs. I didn’t want the sad story. We went from all that to a life of luxury! We’re thankful, we’re blessed, and it’s all a positive mindset now.

Tell me about the album cover and how it ties into this mindset. You’ve never had your face presented so plainly on a project cover before. Was it hard to get to a point to see yourself in that positive light considering what you’ve gone through?

It was hard, and yeah I’ve never been on the cover in a way where you could see my face. It was always an insecurity with my face, and I was never comfortable with the camera and shit. That’s why I haven’t shot a lot of videos cause it makes me feel weird. So even with the cover, to get out of that shell, to put that drip on and stand there and get a close-up of what I’ve been so insecure about, to present what I thought was a flaw, I was nervous about it.

How did that feel?

I loosened up, you know what I mean. I was more nervous about how it was gonna be received and if they’d understand what I was doing.

Do you feel people understand?

Nah. They’re used to Griselda's art pieces and stuff, but we’re grown and we’re glowing man. That’s it.

How do you balance those expectations Griselda fans have? Is it frustrating seeing reactions like that?

It used to be frustrating, but then I had to sit back and realize what we were fortunate to do was make the type of impact that we haven’t seen since the Wu Tang Clan. These fans love what they love, and I’m sure it gets frustrating as a fan too when your favorite artist moves off of the type of stuff you fell in love with. I’m sure Kanye went from Graduation to 808’s & Heartbreak. But you gotta have an open mind when you listen to artists. Let artists create, that’s what it's about. You don’t wanna go to the museum and look at the same painting on every wall.

Going off of that, there’s been a lot of rumored friction between you and Westside Gunn, but a lot of it has come from social media gossip and fans just theorizing based on what they see in interviews and elsewhere. I know you guys have both said that it’s love between you, but how has media coverage perpetuated these kinds of narratives over the years?

I’m gonna be honest a lot of the bullshit I kinda opened the door for myself. Things I might have said in interviews or posted or tweeted, but a lot of times those interviewers make a narrative out of these headlines. They find one little piece out of some shit you said and make it a headline and a narrative gets created. The fans sometimes don’t even watch the whole thing or get the full context of what you’re saying. They just read that headline and just run with their own theories and shit so that gets frustrating. Words get twisted.

When did people start thinking that there were issues between you and Westside Gunn?

I think people had their little theories before that Breakfast Club shit but I ain’t gonna lie that Breakfast Club shit didn’t help. I didn’t do myself no favors with that.

What did you learn from that experience?

Don’t do no interviews *laughs.* Nah man I just understand now how it works. So I just watch what I say and try not to be as honest as I usually be in interviews. I don’t really know how to turn that shit on and off. People ask me and I’ll talk about whatever because I got nothing to hide, but sometimes you gotta harness that.

You speak about Ye a fair amount on Won’t He Do It, and about a conversation you had with him on “Kanye.” How do you relate to his musical impact now that you’re starting to take similarly big creative steps like he did?

I’ve just been watching him and was fortunate enough to get into close proximity to him and see it with my own eyes. Artists like that can’t be knocked down off their pedestal. In their mind, they’re the greatest and you gotta have that self-confidence and belief at that level. It might sound crazy to people, but I was like that growing up. I was like, ‘I’m gonna be on magazines just watch. I’m gonna have a song with JAY-Z just watch.’ I probably sounded crazy, but that self-belief has gotta be strong and just not give a fuck, and I picked that up from Ye, 50, Hov.

Considering your age though there must have been a moment along the way where you doubted yourself, especially considering how young a lot of rappers often are when they break out.

I slip up all the time and still doubt myself. I had doubt in my mind this last year-and-a-half, that’s why I didn’t drop no music. That’s why I didn’t do no freestyles. Doubt comes and goes all the time but what I did personally was put positive shit in my mind, and I’ve always looked at everything as a challenge. I can do anything, it might not be right away but I can get it done.

You claim to be DMX reincarnated on “Flesh Off My Flesh.” I know he was a huge fan of Griselda and was working with you guys closely on “Hood Blues” before he died.

I’m gonna be honest I don’t think I got a chance to meet him. He had left the studio by the time I arrived. I think West and Benny and them was there, and we recorded that song in Atlanta so I had to fly in and by the time I landed it was late night and they were like, ‘X went home he wasn’t feeling too good.’ But he always spoke highly of me, and always spoke highly of Griselda and loved us. We were some of his favorite dudes before he passed. I wish I got a chance to vibe with him and understand him, cause I met his kids and his family.

That bar is gonna raise a lot of eyebrows I’m sure.

It was the grimiest shit I could think of *laughs.* DMX for me is one of my favorite, favorite, favorite artists ever. His energy was unmatched. There will never be another DMX again, but that was me just beating on my chest like I’m King Kong.

When did you start to tap into your CEO bag?

When Jae Skeese came around. I heard his music and what he was coming with, and when Goosebytheway was getting his bag. These artists around me are just ill and I came to the realization that I have a little more power than I thought I had.

How did you and Jae Skeese establish your dynamic on “The Chosen?”

Conway: When we heard that beat I didn’t even know bro was over there [in the corner of the studio] writing some heat. He really just jumped in the driver's seat after that beat changed, cause I was drunk and shit and I ran out of words. I just followed his lead cause he came with the hook.

Jae Skeese: The first time I got around Conway he just told me to always be ready. So anytime I’m in the studio with him I’m just writing anyway just in case. So we was in the studio down in Miami with J.U.S.T.I.C.E. League and I wasn’t even on that trip thinking I was gonna be rapping, but that beat was so crazy so I’m just writing in my phone. Then he told me to put four on there and the energy was just so crazy in that room.

Going off that, tell me about 7xvethegenius’s closing verse on “Won’t He Do It.” Why did you think she would be a fitting end to your project?

For some reason when I heard this record, I just had the idea about Love just rapping until she ran out of oxygen. I wanted her verse to be the moment of 2023. When we look back at this year we gonna be talking about that verse, like how we were talking about Nicki Minaj on “Monster.” It’s one of those moments, or Foxy Brown on “Affirmative Action.” Just going crazy on there. I just want everybody to shine and get their shine off. It ain’t always about me.

You said you made six albums worth of music in Denver, does that mean another album is coming?

I got another album coming out this year fully produced by J.U.S.T.I.C.E. League, and I got a record on there about my dysfunctional relationship with my son and my son’s mother. It’s a transparent record and I only had a hook and one verse on there, and I sent it to [JAY-Z] and he gave me an idea about how to come on the second verse. He’s given me a lot of advice. But the records on Won’t He Do It were just so fire and I was in a space where we were just cooking in Denver. We came out with a masterpiece and this next one is gonna be a different vibration.


Mackenzie Cummings-Grady is a writer based in New York. After getting his start writing for The Boston Globe in 2015, he moved to Brooklyn in 2017 and has since written for numerous publications including Complex, Billboard, HipHopDX and AltPress.