Charlotte Day Wilson and the pursuit of greatness

For Canadians like Wilson, it's become a sort of rallying cry, a unifier in strange times, and an awesome example of what high-level impact can look like for Canadian art. That’s a long way of saying that it’s given the Canadian creative community something to be excited about. Wilson is all for that and has dedicated her life to creating and being part of those wins, too.

“Honestly, I have so much pride for it,” she tells me. “All I want is to have them let me be part of it in some way. Like, please put my music in it, or let me skate. I play!” As we exchange a laugh, I promise that I’ll put her wish on the record. Jacob Tierney, you heard it here first: Charlotte Day Wilson wants in.

“I played hockey very seriously growing up," Wilson continues. "Like, I played at the top, top level. It taught me how to be committed to a practice. But, the episode where [Scott] brought his boyfriend down on the ice, I bawled my eyes out! I didn’t realize it was healing something in me that I had suppressed for so long.”

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Born and raised in downtown Toronto, Charlotte Day Wilson has become one of the city’s most successful musical exports. She came up alongside Daniel Caesar, BADBADNOTGOOD, Saya Gray, and others in the mid-to-late 2010s, building the futuristic, blues-infused sound that the city’s modern R&B/indie scene has become known for.

The circle Wilson runs in is one of a few that have helped reinvigorate Toronto’s global creative image and put it on the map. Representing the city well, as I discover, has always been and continues to be important to her, and part of that is because of how much it invested in her when she was just getting started. “I just feel grateful that I was at the right time in the right place where there were other people doing amazing things and we all banded together,” Wilson says. “We were stronger together than alone.”

When I meet Wilson, we’re in a neighbourhood not far from where she grew up. We’re sitting inside Tutto Panino, the sandwich shop Wilson opened in May 2025 with three close friends from the city — Kaitlyn Lasagna, Andi Larocca, and Paul Liliani. Tucked away in Roncesvalles, one of Toronto’s hottest west-end enclaves, Tutto Panino has become a local hot spot. For weeks after it first opened, the lines were down the block. Today, though, it’s quiet. Chef Lasagna is downstairs figuring out a Roman focaccia to serve at a catering event, sending notes of garlic and tomato wafting through the kitchen and front-of-house. Wilson invites me back behind the counter to watch the process unfold in real time, and I’m in awe. It’s a labour of love, an effort of open-hearted communal generosity. Later, when we wrap up, I get a piece of the focaccia for the road.

As we talk, Wilson and I are perched on a bench near a window, drinking drip coffee as morning regulars cycle in and out. We chat with a few passersby, and we hop to our feet to help make space for a delivery of sodas and drinks headed for the shop’s beverage fridge. The whole place feels like a second home. Having spent many years constantly on the road or living away from Canada's biggest city, that energy is something Wilson tells me she was craving.

Toronto has always been Wilson’s home base, but she spent the last three years living full-time in LA with her partner. Now, she’s returned and made the move even more permanent. “This is the first winter that I’ve spent here in ten years,” she tells me. “It was just nicer to spend the winters there. It’s nice to be able to come somewhere and want to be in my community. If I don’t have something to do, I just pop down here and hang out and listen to music."

The shop’s soundsystem is as superb as its sandwiches: Classic B.B. King, Fleetwood Mac, Anita Baker, and Stevie Wonder soundtrack our conversation. As I learn, this was the music Wilson grew up on and was first influenced by — especially classic Motown — and so it feels only right those sounds are brought into her latest venture.

In true Toronto fashion, the restaurant wouldn’t have been complete without at least a sprinkling of advice from The Bear actor, chef and Pig Pen vocalist Matty Matheson, who Wilson says is now a good friend and was a big part of the shop’s opening. “I would just call him and ask for advice when I was starting this up,” she tells me.

The best words of wisdom he had for her, though, weren’t really about food preparation techniques or restaurant business models. Rather, they were a life lesson as applicable to working as a recording artist as to working as a restaurateur: “The most important thing that he said to me was [about] making sure that between the people who run the businesses and those who work here, we take care of each other. The job of serving people food is to take care of them. Basically, it’s a love language, and you can’t do that effectively unless you’re doing that internally."

It’s impossible to make someone feel welcome in your kitchen if you don’t feel good being there yourself. Similarly, it’s impossible to make records that people want to listen to if you don’t love them too.

Wilson’s journey in music started with classical piano lessons as a kid. “I was not allowed to quit,” she emphasises. “That was not on the table. My dad had quit when he was young, and he was just like, ‘I’m not letting you quit this thing.’ I had a bit of a love/hate relationship with the piano, because it wasn’t something that I chose to do per se but did give me a foundation of really solid ear training. I can’t imagine doing all of this stuff without having had that.”

Early on, she was interested in Ray Charles, Stevie Wonder, and the greats of the Motown era. A key gateway was the Ray Charles biopic, Ray, that her parents played for her when she was young. Also on constant rotation was Standing in the Shadows of Motown, a documentary about the session players who helped bring the label’s iconic cuts to life. “Motown was really the foundation of my musical upbringing,” she says. “That and the Beatles.”

She subsequently moved to Halifax for university, where she played in a band. As much as she loved the creative, she often found herself at the centre of her band’s business, too. “I was creating business plans and routing tours for us and communicating with promoters. I was organized in that way. I think at a certain point, I was like, I wonder maybe if it’d be easier for me to just do this on my own,” she says. At that point, she realized it was time to head back to Toronto.

Wilson quickly picked up an internship at Arts & Crafts, the iconic Toronto indie label founded to help release music by Broken Social Scene that ballooned into a creative powerhouse both in Canada and beyond, putting out records from Canadian talent including Mustafa, Feist, and Lowell. To make money on the side, she also put in shifts as a janitor at a local church. And alongside all of that, she started making her own music.

Wilson's bosses at the label noticed her raw talent: “I showed someone there the music, and they were like, ‘Oh, this is really good. I’m gonna help you put this music out,’” she recalls. Her internship turned into a full time role, given to her not necessarily because the label needed her on the business side but because they saw potential in her creatively: “I think that was their way of being like, ‘We believe in you.'"

Most of her work was fulfilling mailroom orders, packing vinyls, and budgeting tour expenses. But outside of her official duties, the Arts & Crafts team made good on their promise to help her. At the time, she hadn’t even thought much about trying to make it as an artist. Producing and songwriting just came naturally but her sole focus was loving music and wanting to somehow make money working alongside it. Once she started dropping her own work, though, she realised that working as a full-time recording artist might actually be possible. Those early releases far exceeded her expectations and she gave up working at the church and eventually quit Arts & Crafts too. “That’s when I became a musician,” she tells me.

She started with 2016’s CDW, an EP that launched her into the high echelons of critical acclaim. From there, she kept building, putting out more of her own material and doing it her way until the time felt right to level up. That time finally came in 2023, when she signed with XL. “I always thought they were one of the only labels that still felt relevant to me and had an identity,” Wilson says of her decision to finally partner up. “They really care about the music, and I haven’t had any pushback from them about anything that I want to do. Like, when I was putting out my last project, I took all the features off last minute, and they were all just like, ‘Ok, yeah.’”

In 2024, she dropped her second studio album, Cyan Blue, representing another step up. The project earned her a GRAMMY nod — her first — and brought in a prestigious partnership with Red Bull to perform the record at Toronto’s Roy Thompson Hall last spring. “I love highly proficient people. That just gets me going, people who are the most capable, where the mistakes are minimal. That was just an amazing experience to work with an amazing team of people — all the performers were insane,” Wilson says.

Aaron Paris (Ariana Grande, Kehlani) worked on the arrangements with Wilson, and together they created a show that told the story of a life lived through loving music. “People ask me what inspires me to make music, but it’s always other music," she explains. "Other music is my biggest inspiration." The duo sifted through the songs that defined Wilson's life — at least 100, she guesses — and created a series of intricate mashups, covers, and symphonic flips of Wilson’s own R&B work.

Wilson is quick to give Paris credit as a prodigy and while she's right, I can’t help but feel as though she's selling her own talents short. Talking to her, it’s no secret she’s a student of greatness and seeks greatness within herself. That kind of attitude towards one’s craft is magnetic — and is working, if the Marty Supreme rollout has told us anything. “Sometimes people ask me for advice about finding their voice as an artist or whatever," she tells me, "and I’m always like: ‘Well, what do you listen to? Have you studied the greats? Who are the greats to you?’ You have to have really dissected what’s going on in the music."

Wilson returns again to Stevie Wonder: he was that first “great” for her, the type of musician she studied rigorously as a kid, pouring over the lyrics, melodies, production, and arrangements. “He’s a multi-instrumentalist and played a lot of things that we hear on the records. Just insane musical mastery, complex harmonic songwriting, but also this ability to find hooks that translate on top of pretty complex key changes,” she gushes.

Wilson certainly is honing those abilities within herself too. This week, she releases the seven-track Patchwork EP, a collection of songs that pulls from Wilson’s classic sound while also dipping into her most experimental territory yet. Emboldened by an unexpected period of free time, the new record sees her come back swinging to show off her production skills.

But originally, Patchwork wasn’t the plan. Wilson had other things in the works for 2025, but when it became apparent that it wasn’t yet the right time for those plans to materialise, she looked for something else to do. “I don’t want to have too much time between projects where there’s nothing, so then I just decided to do an EP,” she explains. “I also find the format of an EP to be really liberating as an artist, because you’re not like, Oh, this is my next body of work and it has to be something significant. You can kind of be a little bit more creative and experimental with EPs.”

Part of what encouraged that exploratory spirit was Wilson’s close friendship and creative partnership with fellow Canadian Saya Gray. Wilson and Gray have now known each other for almost a decade, brought closer by sharing a studio space a few years back. When they were in sessions at the same time, they’d occasionally pop by to check on the other and offer feedback. Last year, they finally reconnected in a more involved way.

“I would say in some ways she executive produced the EP. She thinks like a producer,” Wilson says of their working relationship. To note, Gray is credited as a feature artist on “Lean,” one of the EP’s pre-release singles, but Wilson says the partnership was much deeper than that. “For me, a producer is also someone who can tell you not to do anything else," she tells me. "And she did a lot of that with me for this project. I showed her the demos and she would just be like, ‘Your production is sick. Just let it be what it is. Don’t bring it to someone else.’ I don’t know whether that’s executive production or just a good friend.”

Gray had a breakout moment too, almost a nice dovetail with Wilson’s own journey. In Wilson’s words, it's been hard-earned, coming on the heels of difficulties with rights management and the slow grind of making it in music. “She’s so talented, she’s so skilled, and I find her music to just be truly so interesting,” she says of her friend.

Was her work with Gray on Patchwork indicative of a broader connection to the “Toronto scene”? Wilson isn’t so sure and reminds me that much of the time since she first started putting music out has been spent abroad, and it’s only really now that she’s back here.

She does wonder often who the next generation of Toronto creatives will be and what their throughline will show up as – she’s sure it will be good, but she’s just been focused inward lately. And on Tutto, of course. “I don’t know as much what the ‘scene’ is anymore here," she elaborates. "And in some ways that’s liberating, because I think it’s important to feel kind of isolated and bored sometimes with your environment. For me personally, isolation and loneliness and a cold winter in Toronto is something that breeds a lot of creativity for me. This isn’t necessarily how I feel all the time in Toronto, but there’s less of a scene here. A lot of people leave. My current creative scene here is pretty contained to the people I play with live. And also Saya Gray.”

Enjoying a more chilled-out Toronto life also helped Wilson recalibrate her priorities in a way she says she needed. Constantly on tour, the focus was handling the pressures of essentially being the CEO of her own business. Within that, she would experience moments of extreme imposter syndrome, resulting in a tendency to close herself off to those around her. With more experience, she’s been able to turn those insecurities into gratitude and tap into a more grounded version of herself. “Knowing yourself first is the toughest battle, especially early on,” Wilson says. “People tell you what they think you can be, and you want to listen to them because it’s exciting when people tell you you could be a star.”

What Wilson wants now, though, isn’t necessarily stardom. Rather, she’s built her career to a point where she both earns more than enough and can still “fly under the radar.” Perhaps the most unbelievable part is that she can sustain herself and her partner purely off making art – but she’s not complaining. “It feels like a blessing to not need to be hyper-visible off the time,” she says. “I pop out when I need to, and if I want to just take some months off to not be a public person, I can easily do that. I feel really grateful for that. The level of gratitude that I have for where I’m at does make me show up for the people around me in a different way. I want to rub off on them.”

With that, we return, somehow, to sandwiches. It really is all the same principle. In everything Wilson does, she’s looking to achieve the greatest good. She’s turning her creative instincts and entrepreneurial tact into vessels to serve others while also following her own inspirations. The more she talks and the more I observe the life she’s built, the more I think she’s cracked some kind of secret code.

After our conversation, Wilson goes back into promo mode for Patchwork — lightly. She’s already started a warmup press tour with a series of parties for diehard fans in both New York and Toronto. She and her team pressed a limited number of unmixed, unmastered copies of the EP and planned to give them out to a select few at the shows. “It’s just a cool way to create a collector’s item, basically,” she tells me.

“It’s nerve wracking though,” she admits. “This music isn’t even out yet, and I’m watching this person leave with it in their hand.” Such is the journey of a project: first, it’s all an artist can think about, and then it becomes fair game for the world to pick apart. That said, Wilson isn’t too phased by it.

“Finally now the music is coming out,” she says and smiles. Her plan is, for the most part, to let that speak for itself. What promotion she does choose to do will be intentional, well curated, and always tasteful. That’s the way she’s gotten to where she is, and she has no intention of changing. “I don’t want to overdo it for my spirit,” she says. “I just want the music to come out. I’m proud of it. I know people are gonna like it. I’m not gonna whore myself out to hope it does well.”