Ricky Montgomery began rehearsing for his tour in late January. The singer/songwriter played shows across America before heading to Europe, Asia and Australia, returning to the U.S. in June. “It had been a long year, and I was also sick,” he says. That’s when he found out his label had dropped him. 

“There was a disconnect as far as creative direction,” he explains. “The label didn’t really know what to do with me, and instead of listening to my ideas, they just tried to apply standard pop templates. Ed Sheeran was the one they thought would work.”

That “disconnect” is the subject of Montgomery’s upcoming single, a downcast acoustic ballad out October 24 called “Superfan.” He sings with a deflated quaver: “Team just got the numbers in/Said try it more like Ed Sheeran/But he’s not me, and I’m not him.”

Being dropped hasn’t hurt Montgomery’s career, though. In fact, he’s now earning more streams — around 2 million streams a day across his catalog — than he was previously. “For better or worse, it’s a social media content game now,” says the 31-year-old singer, who has close to 2 million TikTok followers. “So if you’ve been investing your time into that, the odds are that you’re going to be totally fine if a label decides to drop you.” 

Getting dropped is in vogue this year: Two of the biggest breakout artists of 2024, Chappell Roan and Shaboozey, were both cut by major labels before their recent explosive success. And more acts could soon join their ranks, because the major labels have been cutting costs by slashing staff — and dropping artists.

“Each time there have been major staff layoffs across the label systems, concurrently there were artists released from rosters,” says Leon Morabia, a partner at Mark Music & Media Law. “Some artists are really happy about it and relieved, and some artists are very upset. Their reaction ultimately depends on how much they depend on the record company to do what they do.” 

Dropped acts lose access to an extended support team; plans for upcoming releases must be jettisoned or heavily reworked; tours can be scrapped. That said, Lulu Pantin, founder of loop legal, is adamant that “being dropped has no bearing on long-term success.” And this is probably more true than ever. 

During a recent interview with Bloomberg, Sony Music CEO Rob Stringer pointed out that when he joined the music industry in 1985, labels had a lock on manufacturing, distribution and radio. “We had a lot more power,” he said. Today, in contrast, “the artists have at the very least equal power to us.” 

That’s because they can make music cheaply, and promote it internationally, without ever leaving the house. “Artists have to be as good, if not better, at marketing as any professional marketer now,” Montgomery says. “They are, by default, the most experienced person in the room in marketing meetings.”

At the same time, the buttons that labels can push — to get radio play, appearances on award shows and late-night television, and prominent press placements — no longer guarantee real fans. As a result, Montgomery says, “Labels only want to focus on Tiktok or Reels or YouTube Shorts right now. I had three times as many meetings about TikTok strategy as I did about music. There’s no reason you can’t do that stuff on your own.”

Still, getting dropped can be jarring, a corporate version of a breakup. And like a breakup, disentangling takes a while, as it requires additional negotiation between the artist’s team and the label. “It’s not just, someone waves a magic wand and then you’re dropped,” says an A&R who left a major label job earlier this year. 

This legal wrangling can be crucial for the next phase of an artist’s career. In a typical record deal, the label enjoys exclusive rights to any songs delivered during the contract period — even if they haven’t come out yet. For artists who are being shown the door, then, “the key point is who gets ownership of the unreleased music,” Pantin says.

Record companies are reluctant to give these rights up, since they helped fund the songs’ creation. To secure the return of unreleased music, artists may have to give the label a concession, either in the form of “an ‘override’ payment or a royalty on sales and streams,” Pantin adds. 

If the label refuses to give up the rights to unreleased songs, artists have one other option. “I’ve called labels and asked them to waive the re-recording restriction,” says Tiffany Almy, founder of PKA Law. The re-recording restriction is in place to prevent an artist from putting out a competing version of a song the label already released, a tactic made famous by Taylor Swift with her Taylor’s Version album re-recordings. But the restriction serves no purpose if the label never put out the track in the first place. And if the artist succeeds in convincing the record company to nix that provision, they can then re-cut their music  — on their own dime this time — for release.

Another point of negotiation when artists and labels are uncoupling: The act may be able to obtain some additional money, depending on the structure of their contract. “The deal could be worth $500,000, and $150,000 is given to the artist on signing and the rest is for recording,” the former A&R executive explains. “Then when you deliver the album, whatever’s left from the fund is supposed to go into the artist’s pocket.” 

Attorneys try to prepare for these situations long before the label is even thinking about trimming rosters by including what’s known as “a pay-or-play provision” in the artist’s initial contract. (The initial deal negotiation period is when lawyers push for other protections as well: “I always try to build in caveats that the re-recording restriction doesn’t apply if the track doesn’t get released within a certain period of time,” Almy says.)

The pay-or-play clause ensures that, “If you get dropped in the middle of the contract period, you will be entitled to at least a portion of the remainder of the fund,” explains Oren Agman, an entertainment attorney. “Labels are now capping that, so they’ll give you maybe 30% or 40% of the balance. [But] if you have no pay-or-play provision, then you’re not getting anything other than the advance.” Jodie Shihadeh, a music lawyer, calls this provision “one of the last key points” when negotiating a record deal. 

While the lawyers for both sides go back and forth after an act is dropped, the artist may be stuck twiddling their thumbs. “I’ve seen labels delay responses for months, extending the process and keeping artists in limbo,” Pantin says.

That limbo period matters because an artist technically can’t sign a new deal before getting out of the old agreement. Some do so anyway, figuring a label that dropped them isn’t likely to spend money suing them for breach of contract. “It can be a game of chicken,” the former A&R notes. 

For an artist’s collaborators, it may be more than that — they don’t have the potential cushion of a pay-or-play clause. Many labels give a producer half their fee for a track up front, and fork over the rest only when that track comes out, Almy says. A dropped artist may mean a shelved track; for a producer, a shelved track represents lost income. “I’ve called the A&R at the label that dropped the artist and asked them to consider paying the producer for the work that they already did,” Almy says. Mixers are often in the same predicament. 

Artists have it easier, because they can just start recording and releasing as they see fit. “I’ve seen some artists where it really helped that they got dropped, even though they didn’t want to be,” Shihadeh says.

Another recent post-drop success story is Gigi Perez, who parted ways with Interscope earlier this year. “I was stuck inside of a machine that didn’t work or make sense for me and I was unhappy,” she wrote in a lengthy message on Instagram on March 8. “I think a ton of artists were/are in this position as this new model of the music industry changes.” 

She ended her post on an upbeat note: “Let’s go, bitches.” And in July, she released “Sailor Song,” a muscular folk track that works as well in an arena as it does around a campfire. It proved to be effective on TikTok as well: Users were soon soundtracking tens of thousands of videos with at least three different snippets of the single. 

Streams of “Sailor Song” shot up. And on October 8th, Perez announced a new label home: Island Records.

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From headphones to speakers, Kim Kardashian and Beats have officially extended their partnership with the release of the Beats Pill in limited-edition light gray and dark gray colorways.

The Kim Kardashian x Beats Pill became available on Friday (Oct. 18) via Apple.com/beatsxkim and Amazon.com/beatsxkim. The speakers will also be available in select Apple stores.

“I’m excited to be back with my Beats family and to bring two new colors to an iconic product,” said Kardashian. “Music is a big part of my everyday life, from morning gym sessions to creative brainstorms, and the Beats Pill makes it that much more beautiful.”

Compatible with Android and iOS, the new Beats Pill comes redesigned with new hardware and capabilities including up to 24 hours of battery life and USB-C charging.

Beats introduced the all-new Beats Pill in June. The IPS7’s dust- and water-resistant Bluetooth speaker is compatible with laptops, cell phones and other Pills speakers. (The Beats Pill features Amplify Mode, which can be accessed by synching two speakers together.)

Over the last two years, Kardashian and Beats have collaborated on special colorways of the Beats Fit Pro and Beats Studio Pro, now available in three signature earthtone colors.

In honor of this latest launch, Beats debuted a new campaign starring Kardashian and Saturday Night Live comedian Ben Marshall, titled “Kim’s Pill Assistant.” The clip showcases the reality star’s life through the lens of her “assistant,” Marshall, whose job is to curate the perfect soundtrack for each room that she walks in.

Watch Kardashian’s Beats Pill commercial below.

The last time Audrey Nuna released an album – 2021’s A Liquid Breakfast – the world was still largely in the shadow of the COVID-19 pandemic, Olivia Rodrigo had just launched her Sour LP and Taylor Swift was the very beginning of her Taylor’s Versions campaign. Three years later, Nuna returns with a darker, grittier companion to A Liquid Breakfast titled Trench. 

Featuring a collaboration with Teezo Touchdown and an interpolation of Brandy and Monica’s timeless “The Boy Is Mine,” Trench showcases the marvelous sonic evolution Nuna has undergone since first signing to Arista half a decade ago. Foreboding synths anchor apocalyptic anthems like “Dance Dance Dance,” while forlorn acoustic guitar serves as the backbone for quieter, more jaded moments like the evocative “Joke’s on Me.” In the years between her debut and sophomore albums, Nuna moved to Los Angeles and experienced an unmistakable darkness rooted in the city’s synthetic nature around the same time her frontal lobe started to fully develop.  

Trench is born out of the tumult of those years, and throughout the record’s double-disc journey, Nuna comes out on the other side with a greater understanding of how to streamline her idiosyncrasies into a concise project. She raps and sings across the record’s moody, glitchy trap and R&B-informed soundscape, while still leaving room to incorporate notes of rock, folk and dance-pop. All of those styles were on full display at her electric album release show at Brooklyn’s Sultan Room on Oct. 15, which was packed wall to wall with adoring fans who perfectly matched Nuna’s thrilling stage show. 

“I would say the tagline for this project is ‘soft skin, hard feelings,’” Nuna tells Billboard. “I think that really encapsulates the duality my whole shit is based on… this idea of blending things that don’t normally go together. I love beautiful chords and R&B, but I also love harsh sounds and really raw synths. The whole sound is a blend of our tastes – me and [my producer] Anwar [Sawyer,] and that whole first project really helped me carve out the sound naturally.” 

A Jersey kid and Clive Davis Institute of Recorded Music dropout turned rising cross-genre star, Audrey Nuna is ready to enter the next phase of her career with Trench. In a heartfelt conversation with Billboard, Nuna details the making of Trench, how she understands herself as a Korean-American navigating hip-hop and R&B and how the ‘90s informed much of her approach to her art. 

You signed to Arista in 2019. How do you feel that your relationship with them has evolved over time — especially going into this new project? 

I think it’s like any relationship where we’ve been building a lot of trust. They signed me when I was pretty young, and it’s been five years. When they signed me, they were all super excited — and we have an unusual, unique artist-label relationship where we’re building it all together from the ground up. I’m grateful for the freedom to do what I want to do. I’m pretty blessed in the fact that I’ve never felt like I had to do things. I’ve always been able to maintain a sense of independence, which is a f—king blessing. 

Why is the album called Trench? How did you land on that title? 

I really love words. I just love that word, [“trench.”] First and foremost, I love that it’s double consonants in the back and front. I love that it sounds kind of harsh, but there’s also a bit of balance to it. There’s also this analogy of war and defense mechanisms and the hard, brutal reality of that. I think it’s really interesting that when you zero in on something so harsh, you will always see this warm flesh underneath. It’s that concept: we’re all human, but we go through all these hard things that kind of push us against our nature, which is warm. It was just really ironic to me, and that duality was something I wanted to present throughout the album. 

Why did you choose to present Trench as a double-disc album? 

I just felt it would be a great way to showcase the two sides of this character in this world. At the end of the day, while I was organizing the tracklist, I realized that they’re very much one and the same, but almost inverses of each other. I think that this idea of showcasing those. They’re inverse, but they’re also parallel. 

Talk to me about “Mine,” in which you interpolate Brandy and Monica’s “The Boy Is Mine.” How did that one come together? 

I had the idea for that song because I love the romance of ‘90s R&B. The producer I worked with, Myles William, had the idea to reference such an iconic song, and I loved the idea because it was still so current sonically with the Jersey club in there. I think combining those two things was very fascinating to me. Even flipping the original meaning of the song where two characters are fighting over one guy into me making the guy cry instead – it’s more of that harshness that Trench is about. 

Being that you’re a Jersey kid, did you hear Jersey club a lot growing up? 

Actually, yeah! It’s so funny because in high school, and even before then, Jersey club was always circulating. Not as much on the radio or anything like that, but more on people’s phones on YouTube or if you were in the car with your friends. It was so specific in what it was that to now see it be such a big part of the mainstream is really mindblowing.  

You teamed up with Teezo Touchdown on “Starving.” How did that come together? 

I had that song starting with the demo. We were thinking about a feature that was. In the beginning, we were thinking of Steve Lacy or Fousheé. I think my A&R suggested Teezo because he’s been working with him, and it just made sense. “Starving” is also a very pop record, and kind of out of my comfort zone — which is interesting, because for most people a track like that is very left-field. I think having an artist [who] understands what it’s like to stay in a pocket of the most pop song on your record actually feeling like the B-side is really cool. 

It was just really cool to see him do his thing on there because he just brought a fresh energy that you wouldn’t normally expect someone to rap or sing with. He almost reminds me of André 3000, because of the way he makes anything sound good by how he wears his energy. Same with his fashion — the way he wears the clothes is what makes it work. 

What was on the mood board while you were creating Trench? 

The movie Akira. When I made “Nothing Feels the Same,” Akira was definitely in my head as this villain coming into herself – in the movie’s case, himself. It just felt like a soundtrack for a darker transformation for me. On the other side of that, I was also weirdly inspired by more bubblegum-esque aesthetics, and combing those two things. You can hear it on a song like “Sucking Up.” I’m really inspired by the ‘90s, like KRS-One, but also PinkPantheress and jazz influences like Chick Corea or Hudson Mohawke on the dance side and even Korean 90’s alternative artists. There’s a lot of different stuff. 

What was the entry point to hip-hop? 

I grew up pretty musically sheltered. My parents are immigrants, so they put me on to some Korean older folk music. Knowing popular music came very late. I specifically remember listening to [Ye’s] Yeezus sophomore year of high school for the first time. At that point in my household, cursing was bad. To hear something so vulgar and raw and different from anything I’ve ever heard before, that was a bit of an entry point for me. [I found a] space and form of expression where you can truly say what’s in your heart and not necessarily care about the world. I think that was very enticing to me.  

Meeting Anwar and listening to everything he put me onto and obsessing over Sade together [was also formative.] Sometimes, I feel like when you don’t know what your lineage is because of immigration and you don’t see a lot of people doing what you’re trying to do, you have more freedom because it’s a blank canvas.

How do you navigate conversations where your race is emphasized in relation to the kind of music you make? How do you understand yourself as a Korean-American operating in traditionally Black spaces like hip-hop and R&B? 

Being boxed into “Korean-American” is definitely a thing. In my case, I learned to acknowledge that I am who I am, and being an American is part of my identity, but it’s not necessarily the only thing that you want to be attached to your identity. At the end of the day, we’re human. Yes, I grew up eating kimchi jjigae, my parents spoke Korean to me, I was exposed to all of these other Korean things – that’s gonna bleed into everything I do, whether I want it to or not. 

At the beginning of my career, seeing the hyper-emphasis on [my race] was very interesting because growing up I never felt Korean-American, I never felt Korean enough. And now it’s like you have to be “very” Korean. It’s very extreme. At this point, I’m all about paying respect to where the genre comes from and understanding that I am a visitor and a guest. It’s about respecting the craft and studying it and not viewing it as anything other than what it is – something that is worthy of all of the respect in the world. Also keeping the conversation going and asking questions, I’m not gonna understand every last reference.  

I honestly feel it’s been an evolution. All these cultures are merging, and I think that’s a beautiful thing. Ultimately, I pray that that would give us more empathy and understanding as a human race. My biggest thing is encouraging people to educate me constantly and keeping the conversation open. On both sides, you can get boxed into a narrative, but at the same time, it’s all very gray. Generally, just do what inspires you in a conscientious way. Just do shit. 

You’re trying to break through in the wake of the Stateside K-pop boom. Has that phenomenon impacted the ways the market sees you and your music at all? 

The sentiment towards Asian culture in general has changed in the past three years. Growing up, it wasn’t “cool” to be Asian. But it’s like this hot commodity now, Korean culture especially is at the forefront right now. Sometimes, you do get boxed into this “everything Korean is K-pop” [mentality.] I’ve been listed in random articles as one of “10 K-Pop acts to know.” Even labels that approached me earlier in my career were like, “Well, we have all these K-Pop acts, so you would be very welcome here.” At the same time, my music is worlds away from K-Pop.  

It’s gray and it’s nuanced, but at the end of the day, I’m really proud to be Korean and proud that Koreans are being recognized for their excellence in music and visuals and fashion. When I see people who genuinely love the culture push and try to understand it outside of just the aesthetic, that brings me a lot of joy. 

What was your time in Fort Lee like? 

Fort Lee is like the K-Town of Jersey. It was kind of like a retreat. After I went to school for a year and then I dropped out and moved to Fort Lee. I stayed by all these Korean families, almost in the suburbs — but it was right outside the city, so there was a little bit more going on. That place is so warm and nostalgic in my heart because it’s the place where I really found my sound. It’s the most romantic place in my heart because all I did all day was make music. That was before I had a career; it was when I was doing it, not knowing if I was going to be able to do it. 

There’s something so special about that; I realized you really never get it back once that period is over. You can spend your whole life emulating that, but it will never be as pure. I always look up to my 19-year-old self and the fearlessness that came out of true naïveté. 

How do you view Trench in relation to A Liquid Breakfast? Is there a symbiotic relationship between the two records? 

I think they’re very symbiotic, and I love that word. They follow the same character, [she’s] just gone through a bit more shit. The first project is Fort Lee; it’s romantic, it’s curious, it’s pink and blue and springtime. In between [A Liquid Breakfast and Trench,] I moved to LA and as sunny as that city is, there’s a level of syntheticness and darkness that I experienced. [By Trench,] this character went underground for two years and didn’t see sunlight for a long time. 

 And who knows, maybe this is a “part two” and there’s one more part that ends this story. I definitely think [Trench] is the darker counterpart, sonically, lyrically and conceptually. It’s a bit more complex and experimental. At its core, it follows the same character as the last album. Since the last project, so much has changed and so much has stayed the same. 

I see a lot of the ‘90s in your approach to music videos. How did you develop your visual language, and did that intersect with and or influence your stage show at all? 

I’m very ‘90s-inspired for sure. One of the first videos I remember being very inspired by was the Jamiroquai video, “Virtual Insanity.” And then obviously Missy Elliott, and anything directed by Hype Williams. I don’t know what was going on. I just think it was a golden age of music videos. People put so much value into music videos, but they were also so new to the point where people were just trying anything. I think that balance of having the resources and also having an innocence, in a way, towards the craft was so special.  

And Thank God for the internet. I saw the shit that I had never seen before just browsing YouTube; seeing Spike Jonze’s work and the Beastie Boys’ “Intergalactic.” Finding all of those different things and combining them kind of exploded my DNA. Also, my dad used to own a clothing factory in the Garment District. I was mostly around fashion, and I think that was very formative for me. 

Are you planning to tour behind Trench? 

Yes, next year. I’m still figuring out certain things, but I think that it’s essential for me to do this album live. I came up during the COVID era, and I haven’t had an opportunity to just perform for people as a headliner. I’m just very spiritually ready to present an album in that space. 

What song from the album are you most excited to perform live for the first time? 

I’d say, “Baby OG.” I just love it; it never gets old. I sampled my 19-year-old self on that song. There’s a demo from 2019 called “Need You,” and that never got put out. But we just sampled it one day and it ended up becoming “Baby OG.” The meanings of the songs were so parallel. I didn’t realize that until after I finished the song. It’s kind of a meeting of past and future self.  

Do you plan to return to Clive at any point or are you full steam ahead with your career? 

I can’t afford it. [Laughs.] I can’t afford that s–t! I think if I were to go back to school, I would not go to school for music. I’d want to study history or fashion design. 

In a past interview, you named Chihiro from Spirited Away as the fictional character you relate to the most. Is that still true, and have you heard the Billie Eilish song inspired by that character? 

I think that will always be true. I love Miyazaki’s protagonists because most of the time, they’re kids who are just so courageous and wise. I think that was super empowering to see as a kid. That was one of my earliest memories of digital cinema and animation. I have heard “Chihiro” from the new Billie album. She’s so sick. It’s so awesome to see her sonic progression. 

There’s a question Joy Oladokun often finds herself asking when thinking about her career: “If Nina Simone had the internet, what would she do with that?” she ponders. “Like, what sort of Mavis Staples-meets-Azealia Banks tweets would we have gotten from her?” 

The High Priestess of Soul is far from the only artist the folk-pop artists finds herself ruminating on: throughout her conversation with Billboard, Oladokun drops names ranging from Big Mama Thornton to Paul McCartney to Big Freedia. But the artists she often finds herself thinking about, she says, are the ones whose names she doesn’t know.

“I think a lot of my music comes from a place of knowing that not all Black queer people got to live this long or get this far,” she explains. “It feels like I’m fighting with both the idea of progress, the reality of progress and the cost of it.”

A career’s worth of those feelings come roaring out on Oladokun’s stunning new album Observations From a Crowded Room (out today via Amigo Records). Written and produced by Oladokun in the 15 months since her 2023 LP Proof of Life, the new record sees the singer-songwriter wrestling with her current place in the music industry and the world at large. Employing electronic flourishes to accentuate her pointed songwriting, Oladokun examines why it seems that social advancement in the music industry is always two steps forward, one step back.

The idea for the record started after a whirlwind of touring in 2023 — after running through the summer festival circuit and performing as an opening act for John Mayer and Noah Kahan’s tours, Oladokun found herself at the end of a grueling schedule, sitting by a river with her guitar somewhere in Oregon.

“I was on mushrooms,” she giggles. “I was having an emotionally hard time, then. And when the shrooms hit, I saw this moose — and right there, I just wrote the first song on the album.”

That song, “Letter From a Blackbird,” provides the central argument for the album within its first minute. “These days I sure regret how much of me that I have given/ I feel my patience running out, I hear the water sing to me,” she sings, accompanied only by a vocoder chorus of her own vocals. “Blackbird: what did you think you’d run into out here in the wild?”

Throughout the record, Oladokun contends with managing the expectations of her community (the hip hop-infused”Hollywood”), examining the history of marginalized artists (the pop-leaning “Strong Ones”) and her own desire for recognition from the industry (the fiery folk ballad “Flowers”). Punctuating those songs are brief “observations,” interludes scattered around the project that see Joy speaking directly to her audience and telling them, point blank, how she’s feeling.

While she’s become known in industry circles for her tell-all lyricism, Oladokun acknowledges that Observations is something entirely different that her past albums. “In a sort of unhinged way, Proof of Life was a democracy, and this was more of a dictatorship,” she says. “When you’re working with [other songwriters], sometimes you have to sacrifice a feeling or pull a punch just to get something through. The benefit of making this alone was just that, for 40 minutes, I could just be unfiltered. I’ll give you the choruses and hooks you can hold on to, but I also want to be as honest as possible.”

While Oladokun serves as the sole songwriter and producer on the vast majority of the album’s records, a few other songwriters appear in the liner notes — including Maren Morris (“No Country”), Brian Brown (“Hollywood”), Edwin Bocage and Theresa Terry (“Strong Ones”). As she puts it, Observations wouldn’t have been possible had she not made early connections with songwriters throughout her growing career.

“This album is the fruit of so many lessons learned, and people like Dan Wilson and Ian Fitchuk or Mike Elizando, or even like contemporary great songwriters like INK,” she says. “These were people who took time to really pour into me, and said, ‘Here’s what’s great about what you do, and here’s how we can elevate it.’”

The songs where Oladokun gets the most raw see the singer calling out Nashville, and the industry system therein that she says failed her. “Letter” opens with the thought that, if she drowned in a river, the city wouldn’t cry for her, but rather “breathe sighs of relief.” Penultimate track “I’d Miss the Birds” sees Oladokun calling out the town by name, decrying its willful ignorance of her and people like her, while “Proud Boys and their women” continue to thrive.

In the year since she wrote those songs, Oladokun’s feelings on Nashville have only calcified. “Put it in ink, Nashville should be ashamed of itself. I’ll say it as long as they don’t gun me down; this town is so full of s–t,” she says, staring directly into her Zoom camera. “It’s not even because Nazis can walk around freely — that’s a problem, but Nazis are gathering all over the states. My genuine issue is the people who only want to do enough to appear good, but will never lift a finger to actually help.”

In the eight years she’s spent living in the country music capital of the world, Oladokun says she’s watched firsthand as artists and executives praise the “progress” that the city has made socially while Black queer artists like her continue to be ignored. “I am the Ghost of Christmas f–king Past for this city. I am where I am at in my career in spite of this city. In spite the utter lack of support,” she says. “For all the f–king country girls in glitter shorts dancing around with drag queens, how many of them have offered me features or responded to even one of my f–king DMs?”

As she goes on, Oladokun catches herself and clarifies her point. “I want to separate the part of it that can seem personal, the part where it’s just, ‘Oh, people aren’t paying attention or being fair to me,’” she explains, addressing Nashville directly. “I’m not the only Black and gay talent in your city. I am one of a huge, growing faction of artists in your backyard who you don’t support, because you know what it will cost you.”

Her desire to take a breath and zoom out also happens during Observations. On the stirring soul anthem “No Country,” Oladokun looks to the various genocides occurring throughout the world — in an Instagram post, the singer named Palestine, Congo, Sudan and Nigeria as direct inspirations — and yearns for a moral imperative to protect people from harm our increasingly fractured world.

On an album that deals so much with her own personal struggles, Oladokun felt it was important to put her grievances into a larger context. “My job just isn’t that important. Like, my job is hard — but everyone’s job is hard,” she says. “It’s important for me to remember, because I as a human being never want to let this job stop me from being the best version of myself. I can’t let my tunnel vision of what my day-to-day is like distract from what I think the purpose of sharing my music is, which is to give people something to listen to in a weird world.”

That’s also, in part, why Oladokun never tries to offer big-picture answers to the problems she presents on Observations. Not only does she not have all the answers, but she points out that we all have to agree on what the problems are before we can talk about solutions. “It’s so important to name things, and I think a lot of the problems we have as a society comes from our refusal to name things,” she says. “The goal of this record was never to give an answer, but to say, ‘Ow. This hurts.’”

When Oladokun began writing Observations From a Crowded Room, she was considering quitting the music business altogether. When asked where she’s at with that internal conversation today, she shrugs. “My relationship with my job right now … there’s sort of an agnostic quality to it,” she explains. “I believe my career has a future, but it’s so rarely demonstrated in front of me of what it’s like for someone like me to do so. This is the beginning of a conversation — it’s me saying, ‘This is what it’s been like.’ And it’s a little bit up to other people to say, ‘That is what it’s like.’ I can’t be the only one trying to change the culture.”

A wry smile appears on her face: “Ask me again in a year.”