What follows is one of the many articles in the Mercury‘s 2026 Queer Issue. Find a print copy here, subscribe to get a copy mailed to you here, and if you’re feeling generous and want to keep these types of articles coming, support us here.—eds.
Though he has attended Portland Pride celebrations since relocating here in 2017, chart-topping rapper iLoveMakonnen has never performed here during Pride season. That changes next month, when the multi-platinum artist headlines Pride in Demand at the Star Theater. Pride in Demand, a queer showcase on July 17-18 arranged by singer-songwriter Logan Lynn’s queer talent agency Music in Demand, will see the rapper celebrate LGBTQIA2+ Pride, Portland style. It’s his first show of the year by design.
iLoveMakonnen will perform both nights, sharing the bill with musicians Gia Woods and Morgxn; drag artists Jay Colby, Heavy Cream, Quesa D’Mondays, Transjenifahs Gawdy, and Monique Michaels; and comedians Mx. Dahlia Belle, Rochelle Cochran, Guy Branum, and Jeffrey Jay.
“This is what I like to be a part of. I like to have all walks of life and everybody be able to come together and just show them whatever it is—from art, comedy, whatever it is—I just really enjoy bringing all of us together and letting us appreciate all of us, whoever we are, in our uniqueness,” he tells the Mercury..
iLoveMakonnen is best known for his Grammy-nominated 2014 song “Tuesday,” an atmospheric, bubbly track about mid-week clubbing that went platinum after Drake hopped on the track as a feature. Its strength lies not only in its musical arrangement, but in Sheran’s unique cadence and vocal quality—also evident in his natural speaking voice.
“Pride here is so welcoming and enjoyable,” he says. “It’s not too much like competing, like how certain Prides in Atlanta—and this is no shade—but I feel like there’s always someone trying to outdo and updo the other, like there has to be an event that’s bigger than the other, and here it’s just overall a full celebration for the city.”
Sheran naturally gets along with artists regardless of genre, which has led to some collabs that seem puzzling on paper until the tracks come together. He’s worked with Mike WiLL Made-It, DJ Mustard, Gucci Mane, the late Juice WRLD, Santigold, Abra, Fall Out Boy, and Ezra Koenig, to name only a few. His latest album, Everything Is Fake, came out in May, a joint release with the grunge-rap duo Yellow Trash Can that feels like a more mellow, healed version of the emo rap iLoveMakonnen released with the late Lil Peep.
“Portland is such a diverse place, and I love when all the cultures clash,” he says, comparing the city to a house party he once attended in his hometown of Atlanta, Georgia. “That’s one of my favorite things ever…it was just a culture clash of so many different walks of life all here at a house party with everyone having a great time, but if you look at everybody you wouldn’t think they’d talk to each other and bond over similarities, and that’s what I like to bring in my art.”
Being openly out in the hip-hop world still felt revolutionary in the era when “Tuesday” came out—unheard of, almost. Artists like Frank Ocean, Cakes da Killa, CupcakKe, and Mykki Blanco had just recently shattered perceptions about who could and couldn’t be a rapper with their personas, productions, and pen games. Tyler, the Creator hadn’t yet flirted earnestly with bisexuality on Flowerboy, Lil Nas X was years away from the “Old Town Road,” and Sheran hadn’t publicly come out.
“Sometimes I don’t look back. I’ve been so happy with where I am now and where things are that I’m just thankful,” he says.
iLoveMakonnen came out as gay on Twitter in 2017, mostly to positive responses. But members of the trio Migos, iLoveMakonnen’s one-time collaborators, commented on Sheran’s coming out in an interview with Rolling Stone, stating “world is fucked up” and suggesting that his being gay somehow undermined the legitimacy of his lyrics about trapping. In response, Sheran, in his first interview post-coming out with the Fader, said, “Oh well. With friends like these, who needs enemies?” But he had already long learned how to wholly accept himself in his private life.
“Life happens, and I think the best thing for anyone to do—especially somebody like me, being in the public—is to take some time for myself, so that when I’m back in the public I’m not lashing out or having the wrong issues because I haven’t settled them within myself yet,” Sheran says. “I’ve had to understand this responsibility that I have of being a public figure, and I know I can’t not be in a leadership type of role, so I want to make sure that I check myself so I know how to interact and do things.”
Sheran has, in recent years, shifted between two creative poles: his music career, including helping other musicians produce projects at Portland recording studio Burn Money Music, and practicing visual art and fashion design under the moniker Makoregon503. Prior to a fire at Burn Money Music last summer, Sheran was focused on the latter, making both paintings and hand-painted t-shirts. But when the fire destroyed several of his works, Sheran shifted focus to helping BMM’s team recover through both fundraising efforts and production work to clear the studio’s backlog of music projects.
“I personally didn’t think I would be in Portland this long. That just goes to show how happy, healed, loved, accepted, and appreciated I feel being in a place like this,” Sheran says. “I can’t believe how much I’ve grown being in this new space of [maturation]. I’m thankful and appreciate everything that I’ve been through, and I wouldn’t be who I am today and in the space I am where I’m trying to get back out there to be in the public, be a testimonial, to give inspiration to others to let them know that they can find their own paths, too.”
Pride in Demand, Star Theater, 13 NW 6th, Friday, July 17 and Saturday, July 18, 9 pm, $25 and up, startheaterportland.com, 21+.