For most artists, Portland isn’t the place to relocate amid the heights of their career.
But for iLoveMakonnen, relocating to Portland from Atlanta offered a space away from the pressure and attention of the music industry, and the opportunity to explore himself.
Makonnen joins us to share more about his upcoming performance at the Pride in Demand Queer Takeover and what has kept him in Portland nearly 10 years later.
Note: The following transcript was transcribed using AI and validated for accuracy, readability and formatting by an OPB volunteer.
Dave Miller: This is Think Out Loud on OPB. I’m Dave Miller. For some artists, Portland is a place you leave when you hit it big. Makonnen Sheran, otherwise known as iLoveMakonnen, went in the opposite direction. The Atlanta-based rapper and artist had a massive hit in 2014. Then only two years later, he moved to Portland to get away from the pressure and the attention of the music industry. And to be his authentic self, he never left.
Makonnen will be performing this weekend at the Pride in Demand Queer Takeover. That’s Friday and Saturday at the Star Theater, and he joins us now. It’s great to have you on the show.
Makonnen Sheran: Thank you for having me.
Miller: You’ve been making music for what, six or seven years when “Tuesday” hit, just in a gigantic way. It blew up. It went platinum, got nominated for a Grammy, and was on a bunch of best-of lists. That was all a dozen years ago, a big chunk of time ago, half a lifetime ago, maybe. Looking back, what do you most remember about those days when your life changed?
Sheran: I just remember never having time to myself, everyone chasing me around and making as many engagements and appointments as possible. It was a whirlwind of nonstop movement and excitement.
And it got a little overwhelming.
Miller: Excitement and over–. So there were positives to it too. I mean, it was overwhelming in a good and a bad way?
Sheran: Yeah, in a good way because now it’s like people finally see your art, and are appreciating it and celebrating in it. But then also, that comes with the negativity, the rumors and the gossip, and people trying to destroy your relationships and things like that. So it gets a little overwhelming trying to balance the positives and the negatives. You don’t want to end up focusing too much on the negatives because then you lose sight of what’s happening that’s positive.
Miller: Had that been something like your dream? When you were just making music in your own room or even a blogger just writing about music, did you dream about fame like that?
Sheran: I don’t think I dreamt about fame like that. But I did want to get my music out there, be able to perform and have people really engage with the art that I was putting out. For me, the music was a therapy. I wanted to be able to have it be like a therapy for others as well because I know that’s what music did for me during times. And I felt the power of that. I just wanted to be able to share my expression and my music, and it get to people.
The fame and stuff that came with it was extra and it was awesome. But I’d never really prepared or planned to be famous. I just wanted to be able to perform, work and do that thing. I didn’t expect it to go anywhere that it went.
Miller: Do you think you could have prepared for that kind of fame that quickly?
Sheran: No, I don’t think so. I mean, it’s like improvising in real time. So at times, I would remember being at places where … I know me all my life, so I know, right now, I have six good months of people just saying that, “oh, you’re amazing,” you’re all this. And then we’re like at a club and then they stopped David Beckham to push me in. And I’m like, “Wait, wait, that’s David Beckham! He’s like a legend. I’ve only been here for like six months.”
Miller: This is in Atlanta or wherever you were?
Sheran: Yeah, this was in New York, which was even crazier because I’m from Atlanta. So then I go to New York, which is a huge city, and celebrity, fame and all this stuff. And now they’re treating me like I’m of more importance than other people who I would always considered more important than me. So that was kind of shocking.
Miller: Do you mind if we listen to part of a song ?
Sheran: Oh of course.
Miller: OK, this is part of “Tuesday.”
[“Tuesday” by iLoveMakonnen playing]
Got the club goin’ up on a Tuesday
Got your girl in the cut and she choosey
Club goin’ up on a Tuesday
Got your girl in the cut and she choosey
Club goin’ up on a Tuesday
Got your girl in the cut and she choosey
[Song fades out]
Miller: Do you ever just drive around or walk around now and then hear someone playing that in their car?
Sheran: Not as much recently, but I do remember a few times. I remember one time in New York, on the expressway, the guy was playing the song next door. I rolled down the window expecting him to know who I was. [Laughter]
Miller: You rolled down, looking at him, saying, “That’s me.”
Sheran: I’m lookin’ at him, like, “Hey man, that’s my song.” And he’s just like, I don’t know you. He just keeps driving.
Miller: Why are you looking at me? [Laughter]
OK, so all of that is 2014 and then two years later, in 2016, you announced that you were fed up and maybe it was a little bit totally hard to pin down, but maybe done with making music. Why?
Sheran: I was on tour overseas in May and it wasn’t working out. I felt like the media was attacking me, my music was just becoming a second thought of the conversation and all this drama. I felt like for us to keep that position, we had to start fighting or dissing other artists to keep attention, and that just wasn’t something that interested me. And I was having issues from the blogs and the internet, to where I feel like my voice isn’t even being heard. Everybody just wants to hear the drama and the thing that catches the headline. And I was emotionally just overwhelmed and fed up, and was like, you know what? I want to retire.
Miller: What brought you to Portland?
Sheran: Getting away from the music industry or just the whirlwind of the things that I was in. Before my song blew up and stuff, I did five years on house arrest and probation in Atlanta. Then I moved straight to New York. And then it’s like every night I’m out in New York, partying and doing all the socializing, and I really didn’t have any time for myself.
When I went to LA, I was looking at places to live, and I saw Portland. I had these two dogs at the time, and I saw that Oregon was really good for dogs. And they say you could bring your dog to the bar. And I was like, “Oh my God, it’s going to be so good for my dogs.” Then we found a place up here and I just drove up. And I was [thinking] I’ve never even been here. I just want to go and get away to find myself, really.
Miller: Did that happen?
Sheran: Yeah, I think so.
Miller: What do you mean by that?
Sheran: Well, I got to just spend more time with myself and stopped running from, I guess, things that were causing issues in my life and just face them head on. I was able to feel comfortable enough to come out as gay here, which is a big thing in hip hop and rap, where it’s like the ultimate no no. Just being here in Portland, I was able to see people living, just enjoying their life and really not caring about what others say about them. And for me, being in the media, a lot of times the negativity, the comments and things would kind of get to me. So here, I was able to get to myself and see others just being themselves. It kind of inspired me to get that strength to just want to be myself and be out in public, whoever I am, anywhere, without having to hide.
And I think that other younger artists or people who are in the same industry would help them because a lot of these times when, I guess, we’re trying to hide ourselves, we hide in substance abuse and other things like that. I started to see it take down a lot of people and they weren’t able to face the things with support, the way they should have. And so I just wanted to do that. It was very hard for me to do.
Miller: To come out?
Sheran: Yeah, but I felt so much strength after doing it. Of course I lost a lot of friends and a lot of people never called me again who said they’ll be there forever, because I was famous and stuff. But when I did that, it felt good to me because it shows who’s around me for the right reasons, and who really is my friend, and not based on the success I have, the way I look in the public eye or anything like that.
Miller: How much do you think the hip hop community’s approach to queer artists has changed in that time? 2017 is when you came out, so that’s a long time in cultural years. But how much do you think has changed?
Sheran: I think we’ve made some progress, but I don’t think it’s fully embraced or anything. I think for women, it may be a little easier to say that they’re a lesbian, more so than a guy to come out as gay. Because I think the hip hop and the rap thing is based on such machoness and everyone trying to be the strongest, I guess. And I felt that with so many people hiding, in hip hop and stuff, the strongest thing that I could do is come out as gay. So I just lived in the culture.
I’m from Atlanta, Georgia and I’ve seen this forever. One of my things is I don’t want to expose everybody else’s closet, so I’ll just expose my own. That was one of the things I said for me to come out. But I think we’ve made a lot of great progress. I’ve seen a lot of artists be able to get support and express themselves, and show that they have art and it’s more than just your sexual preference. Because I think hip hop, a lot of times, stops from even engaging in the art once they hear about whatever personal little thing you have going on. And I think for me, as an artist, I’ve always wanted the art to speak louder than the person.
Miller: So we talked about your sort of leaving music behind, your fed-up announcement in 2016. You had another one just a couple of years ago, but am I right that you’ve never stopped making music?
Sheran: I love music. It is my therapy. But sometimes, when I announce my retirements and things, I think these are the industry politics that I’m retiring from.
Miller: You’re done on some level. You’re fed up with the music business in that moment, but you’re not fed up with music making?
Sheran: Yeah, exactly. The music business and music industry is different than music making. The music business and industry is always looking for a profit, a hit, and sometimes that comes by any means, even the death of an artist. And for me, music making is a therapy, it’s a fun thing. It’s a hobby. It’s an art. I love doing it. I never really wanted to put a price on it and make it like, “this is my business.” As I’ve been in the music business, it’s been a little hard for me to detach the two, my passion and my art [from] work, business-wise.
So a lot of times like that I just announced that I’m retiring from that stuff so that myself, as an artist, can get back into fully art. And then I can put it out and fans can enjoy it. But I don’t think I’m chasing after a Grammy nomination or trying to reach the Billboard Top 10 and all those great things.
Miller: Let’s listen to a track you released just last year, almost exactly a year ago, called “Is It Love?”
[“Is It Love?” by iLoveMakonnen playing]
Miller: What are your hopes these days when you put out a track?
Sheran: My hope these days is that it gets to the human listener and somehow it is a soundtrack to their life. No matter what thing they’re going through, I just hope that [in] some way, some of my art and music is able to be there for them in a way that music and art was there for me. So that’s really what I do it for. It’s for the listener now.
Miller: Can you tell us about your studio Burn Money?
Sheran: Burn Money Studios. I partnered with my friend Jason who’s been here for many years before me. But he started Burn Money in 2014 as well, and I came here in 2016. They just accepted me with open arms. I would come over and recreate. [We] just started coaching and mentoring a lot of the younger artists and producers here in Portland and Oregon. The studio actually burned down last August in Southeast, but we were able to rebuild a new smaller one that’s in Northeast now. Burnside and 90-something.
Miller: So you’ve been releasing music on and off for years. You haven’t stopped. But how much live performing have you been doing in recent years?
Sheran: Oh man, I think since COVID 2020 I’ve maybe performed six times.
Miller: So the performances this weekend for Portland Pride, they’re relatively rare ones. Why do you want to do it?
Sheran: I love Portland. I’ve always wanted to play at Portland Pride. My agent told me that they were putting together this whole Portland Queer Takeover and asked if I wanted to be a part of it. I was like, yeah, of course, this is my neighborhood. I live here. I would love to be able to perform for my neighbors.
Miller: How are you feeling ahead of the performance?
Sheran: I am a little nervous, of course, because I think it’s my first performance of the year and then we have two nights back to back. So I’ve got some rehearsals and practicing this week. I’m really overly excited, but that’s how I get nervous. So I’m excited to put on a good show.
Miller: Artists often say that when you’re not nervous, that’s when you should worry.
Sheran: Oh yeah, for sure.
Miller: I mentioned you’re a visual artist as well, as Makoregon503. But music, obviously, [is] still a major part of your life. What are you excited to explore next as an artist?
Sheran: I like doing painting and stuff, but I think what I’m excited to explore next is more writing and storytelling. I’m actually working on my book right now, a memoir. And then I’m working on writing out some television series of things I’ve experienced in the past, but have, I feel, good stories that will be able to have lessons in them for many people who don’t have to maybe go through the exact same experience.
Miller: Makonnen Sharen, thanks so much for joining us. It’s been a pleasure talking with you.
Sheran: Thank you so much.
Miller: Makonnen Sheran, otherwise known as iLoveMakonnen, will be performing this weekend at Portland’s Pride in Demand Queer Takeover. It’s Friday and Saturday at the Star Theater.
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