How do you carve out a successful career in music? For Chester Krupa, a 25-year-old songwriter/producer whose work has been streamed more than a billion times on various platforms, the path to success required flexibility and ingenuity. As soon as he began making beats in his first year of University, he began sending them out to potential collaborators. “I was reaching out to people [cold calling], hustling, and trying to start relationships,” he recalls.

This penchant for seeking out and wholeheartedly embracing opportunity eventually led to him collaborating with grandson, the critically acclaimed and commercially successful activist rap/rock/dance singer-songwriter. That partnership opened once unimaginable doors: working with an icon like Travis Barker; producing the song “Rain,” featured in Suicide Squad 2; getting his work into the Fast and Furious movie,  Netflix’s original Riverdale, and in corporate placements for Marvel, Mercedes Benz, UFC, Taco Bell, Microsoft, and Air Canada; winning the $10,000 SOCAN Songwriting Prize in 2019; and more.

Early on, unsure about what career path he wanted to pursue after finishing high school, Krupa enrolled in a General Media Arts program at Toronto Metropolitan University (formerly Ryerson University). He would regularly have to record people and mix audio tracks for class assignments, which sparked his interest in audio engineering – and by extension, music production. He started routinely producing beats outside of class and sending them out to local artists and YouTubers. Within a few months, he was making music for one of the most popular YouTubers in the world, Casey Neistat.

“It was crazy,” says Krupa. “I’ve always been a huge fan of his stuff, and this was right when he was about to do his daily vlogs. I found his e-mail [address] on his website and offered to make him beats. He said yes, and asked me to send him some stuff. I started sending 10, 15 songs a week to him, and he would use them in every one of his videos.”

Meanwhile, Krupa was connecting with local Toronto artists and collaborating with them. His big break came when a local singer-songwriter he was working with, Blaise Moore, was signed by Interscope. “I was trying to leverage that while reaching out to people,” says Krupa, “which was how I met my manager.”

“I jump around a lot. I don’t like [staying] with one thing”

His new manager, Prim8 Music, also represented grandson, and brought the pair together. “He told me they had one song that they couldn’t quite figure out the production for, and asked if I wanted to take a stab at it,” Krupa explains. The song that he helped out on was “Blood // Water,” Grandson’s second-highest charting song to date; For his work on the track, Krupa was a co-winner of the aforementioned 2019 SOCAN Songwriting Prize, alongside grandson and his longtime producer Kevin Hissink. Since then, Krupa has regularly worked with the rock/rap singer, most recently on his 2022 JUNO-nominated album Death of an Optimist.

Most of Krupa’s work is done remotely, sending stems back and forth with Hissink, and sharing ideas via e-mails and voice messages. He feels he’s grown significantly as a producer while working with grandson. “I wasn’t ever producing rock music until I started working with him,” he says. “It was diving in head-first and figuring it all out… People were bringing so many genres into his project – rock, hip-hop, electronic – and trying to meld it together. It’s been a cool process to experiment; throwing things at the wall and seeing what sticks.”

While working with grandson, Krupa has done production on tracks featuring stars like Jessie Reyez, Ke$ha, and one of his favorite artists growing up, Travis Barker. “I grew up listening to Blink 182, and getting stems for Travis Barker drums is a crazy experience,” he says. “I’ve gotten to work with a lot of cool people on a record, [with] so many new perspectives, and learning new tricks.”

The remainder of 2022 will have lots in store: more grandson work is coming out, as well as projects with high-profile artists like Quavo, Jason Derulo, and Swae Lee. Meanwhile, he’s also been working tirelessly on an upcoming solo project.

Recently Krupa has found himself experimenting with pop and dance production, while also making songs specifically for TV shows and commercials. For him, taking risks is still the most important thing. “I jump around a lot,” he says. “I don’t like [staying] with one thing. Constantly doing different genres keeps your production skills fresh.”

Pierre KwendersPierre Kwenders couldn’t be any prouder when we reached him on the phone. “I was really anxious for this album to finally come out,” he says, almost relieved, as he discusses Jose Louis and the Paradox of Love.

Released in April 2022, Kwenders’ third solo album (sung in Lingala, French, English, Tshiluba, and Kikongo) arrives five years after his Félix-winning and Polaris short-listed predecessor, MAKANDA at The End of Space, the Beginning of Time. “I started working on the third one immediately after the second,” he says. “My goal, initially, was to release something in 2020, but we all know what happened… It gave me a lot of time, and I’m very grateful that I had that time. It allowed me to fine-tune my work, to re-write some of the lyrics, and to end up with something near-perfect.”

This time also allowed the Québécois artist to bring together an impressive lineup of collaborators from around the world, including Parisian producer, DJ, and singer Sônge, French-Senegalese artist anaiis, Chilean producers Esqo and Carlomarco, as well as Portuguese DJ and producer João Branko Barbosa, of Buraka som Sistema fame. Through it all, Kwenders acts as a conductor.

“I’m comfortable in that role. My main goal is to give my collaborators space to express themselves, even though they’re in Pierre Kwenders’ realm,” he explains. “We artists generally have big egos. I even have a song titled “Ego” [a 2020 duet with Clément Bazin]. But it’s important to set that aside to give way to a healthy collaboration.”

The song “L.E.S.” (which stands for “Liberté, Égalité, Sagacité”) is a perfect example of this “healthy collaboration” philosophy. Zimbabwean-American producer Tendai Baba Maraire – ex-member of the experimental rap duo Shabaaz Palaces, and Kwenders’s loyal collaborator – initiated the composition, before re-working it with producer and DJ King Britt at his home in Philadelphia.

“It was going well, but I still had no words, something was missing,” says the Montréal-based Kwenders. “And at some point in 2019, I was in New Orleans, and Tendai was there, too. I called Win Butler and Régine Chassagne [the two members of Arcade Fire who live there], and we just started jamming. The energy was unbelievable. I grabbed a mic and we started recording. My voice as you hear it on that track is the actual recording from that jam session. I kept it as is. The problem was that the song was now 35 minutes long!” he laughs. “I came back to it with a clear head, and we boiled it down to a nine-minute version.”

As the album’s opener, the song sends a clear message: “It says, ‘I’m inviting you, welcome to my idyll.’ It’s a journey, a call that begins with the sound of percussion and guitars that build gradually,” says Kwenders. “The energy level slow grows and grows.” Step by step, we enter the realm of this sonically rich and diversified album, which goes through ambient and dance-ier phases, peppered with electro, pop, R&B, Congolese rhumba, and coupé-décalé, Côte d’Ivoire genre that’s conquering the world, thanks to its percussion, African music samples, and penetrating bass.

Jose Louis and the Paradox of Love bears the traces of Kwenders’ travels over the past four years, notably in Santiago, Lisbon, Seattle, New York, and Philadelphia – all of them cities where the album was recorded. “Travelling opens your mind,” says the man who’s travelled the world with his Moonshine events, an evening of music that’s become emblematic of Montréal’s nightlife. “That’s how you come in contact with other cultures, and see how other people live. Each time I leave to go somewhere, I want to discover new artists.”

It would be a misnomer to say Kwenders’ third album is a collaboration album, if only because, in the words of its creator, it’s his “most personal to date.

“These last few years, I was involved in romantic relationships that made me think a lot. Thinking about myself, my sexuality. I felt like recounting my experiences, the man I’ve become,” he confides. “I limited my self-expression for a long time. I’ve learned to be a better version of me while I was working on this album.”

“Your Dream,” a duet with Québécois singer-songwriter Ngabo, is an affirmation of Kwenders as an artist. The song is especially dedicated to his mother, whose voice – on a grainy voicemail recording – can be heard at the beginning and end of the song.

“That song is a love letter,” says Kwenders. “It’s my way of thanking my mom, despite her doubts about my intentions when I quit accounting to dive into music. I came up with this song to reassure her, to tell her that deep down, it’s thanks to the education she gave me that I’m the artist I am today. Our parents have wonderful dreams for us, but sometimes we have different dreams, and we shouldn’t stop ourselves from living them. We must embrace them and live them fully.”


Before he became one of Canada’s most renowned DJs, Charlie B was a kindergarten teacher. In the wee hours, he would be in the club on the 1s and 2s, or in the studio working with then-emerging GTA exports like Tory Lanez or Preme (formerly known as P Reign). By day, he was helping 30 schoolkids learn how to write their names.

“It’s crazy, because during that time, P Reign had a song coming out with Drake,” says Charlie B. “We waited so long to try to get this song; countless hours in the studio, working so hard. And finally, P Reign gets the song with Drake, and it’s Labour Day Weekend, and I’ve got work on Tuesday. I’m over here teaching kids how to walk in a straight line, all while this song was out.” Though Charlie, born Ajay Saxena, juggled teaching and music for three years, in 2016, he decided to make a leap and pursue music full-time.

Since then, he’s toured the world and worked with hip-hop standouts like Cardi B, Rick Ross, and DJ Khaled, the latter of whom he cites as a mentor. Most recently, Charlie released his first full-length album, Across the Board, which features hand-picked talent from all over Toronto. “I’ve been working on [the album] for the last two years,” he says. “It’s my view on talent in this city. I’ve been able to be in the studio and create with these artists. We’ve built these records together, collectively. And I’m super-proud of how it came out.”

For Charlie, in-person recording sessions were crucial to creating the album. “I was really adamant [about] having the artists coming to the studio and us building the song together,” he says. “Saying, ‘Hey, listen, this the concept I’m thinking about, this is the vibe.’ I’d play them some beats from my producers and essentially executive-produce these songs.”

Patience was another key ingredient in his creative process. If a song didn’t quite have the flavour he was looking for, he didn’t try to force things. This approach helped him and Driftwood rapper Pressa come up with the infectious single “Glitch.”

“Me and Pressa were in L.A., and we were working on music, and I just felt like we hadn’t gotten what we could have,” says Mr. B. “I didn’t want to rush it. Just because you lock in a studio with an artist, doesn’t mean that you’re gonna get the record you want the same day. It doesn’t work like that.”

Teacher’s Tips

Ever the teacher, Charlie B has three tips for other up-and-coming rappers.

  • “Never stop networking. Your network is obviously your net worth. Keep expanding on that.”
  • “Be consistent. Never, never give up. Keep going!”
  • “It’s very important to have good mentors and good life coaches in your corner that can guide you. I think we all need that in our lives.”

The creative spark they needed would be ignited weeks later on Charlie’s birthday weekend. He and Pressa were at Quad Studios, the legendary Times Square recording space that’s been used by everyone from Mariah Carey to Jay-Z. A change of location made everything click. “We were in New York, it’s Quad, and I’m working on my birthday,” says Charlie. “[I said] ‘Let’s try’. And we got one out, and we were really happy with the final product. It was in a memorable studio too, so that was even better”.

Known as “Mr. Canada,” Charlie aimed, with Across the Board, not just to put a spotlight on Toronto, but to help illuminate the possibilities for local artists. “I want to give these kids experiences,” he says. “If we can do something to make these kids believe that they can get out of the streets, that’s the most important thing to me. I love seeing the kids in Toronto live their passion; live their dreams. There’s nothing happier for me than to see these kids on the stage doing their thing.”