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Rb Hip Hop
Cover Story: Daniel Caesar's Next Chapter
Tonight, standing before just 600 people, accompanied only by his longtime collaborators Matthew Burnett and Jordan Evans on guitar and drums, respectively, Caesar has his particular magnetism on display; open-hearted and warm, his natural spontaneity and looseness connect him deeply to the fans at this intimate show, part of Billboard Canada’s THE STAGE at NXNE. They sing along to nearly every word.
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Admittedly a little drunk and a bit high on mushrooms, Caesar is reflective and verbose: His tender vocals do the talking — but so does he. “The last time I played here, I was 21, 22,” he says from the stage. “Now I’m 30, and it’s really cool to see a bunch of people who look the way I looked the last time I played here… I was a scruffy-ass…in these Toronto streets. I was basically a homeless kid.”
He recounts how, on his way to the venue, he passed many of the most meaningful spots from his early career — days when, estranged from his parents as a teenager, he’d traveled from the suburbs to the city, jumping between friends’ couches and occasionally park benches.
“It’s a full-circle moment,” he continues, finally arriving at the right words. “And yeah, I could have just said ‘full-circle moment,’ but my feelings are complicated and I’m trying to communicate them to you.”
It’s the right moment for the singer to return to his roots. The moody, introspective wave of genre-blurring R&B that Caesar helped usher in over the last decade has gone fully mainstream, and Caesar himself has reaped some of the rewards — he won a 2019 Grammy Award for his “Best Part,” featuring H.E.R.; was featured alongside Giveon on Justin Bieber’s “Peaches,” which debuted at No. 1 on the Billboard Hot 100 in 2021; and his fruitful collaboration with Tyler, The Creator played a big role in sending the rapper’s 2024 album, Chromakopia, to No. 1 on the Billboard 200.
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But for Caesar, the past few years have been a bit bumpier as he’s confronted the pressures (and consequences) of fame, independence and his own penchant for emotional honesty.
Now, reunited with the team that initially propelled him, he’s getting ready to release 2025’s Son of Spergy, his first new album since 2023’s Never Enough, later this year. He says he’s in a purer place: older and wiser, seeking his early innocence yet ready to move forward. The album’s first single, “Have A Baby (With Me),” comes out July 25.
“I feel like we’re picking up where we left off,” he says. “I almost feel like I’m starting again — and I love it.”
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Heather Hazzan
Born Ashton Simmonds in the Ontario suburb of Oshawa, Caesar grew up in a religious Seventh-day Adventist household. He clashed with his parents as a teenager and eventually dropped out of school and moved to Toronto, couch-surfing with friends while he pursued his music career. In 2015, he linked up with Evans and Burnett (who he’d known since 2012) as well as a handful of other Toronto creatives to form Golden Child Recordings, an independent collective of artists and producers that also acted as a label and his management.
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After a pair of well-regarded EPs, 2014’s Praise Break and 2015’s Pilgrim’s Paradise, the singer’s 2017 debut full-length, Freudian, was hailed as an instant classic. The romantic “Best Part” with H.E.R. and “Get You” with Kali Uchis both cracked the Hot 100 and reached No. 1 on the Adult R&B Airplay chart, the former for four weeks, becoming enduring modern standards of the genre; recently, they both appeared on Apple Music’s list of the most streamed songs of the last decade.
In the city that had produced global superstars Drake and The Weeknd, Caesar was touted as the next big thing — the hottest name in the wave of local talent that included artists like Jessie Reyez, Charlotte Day Wilson and BadBadNotGood. Big-name collaborators like Pharrell Williams and John Mayer started to call, and so did major labels. But in 2019, Caesar hit a public roadblock that slowed his momentum and led him into an identity crisis.
“I was on a path, and then a lot of drama and controversy that I didn’t foresee entered my life and I got knocked off the path. I had achieved [the success] that I always wanted, and then I felt like I was going to lose it,” he says. “For being myself.”
A few months before the release of his second album, Case Study 01, Caesar went live on Instagram while visibly intoxicated and launched into a rambling defense of YesJulz, a white female influencer who had been accused of cultural appropriation and making disparaging comments about Black women. He questioned why Black people were being “so mean to white people,” adding, “That’s not equality.”
The backlash was swift. He didn’t suffer an immediate industry freeze-out, but there was a noticeable chill, some of it self-imposed: Caesar retreated from the public eye, posting less on social media and giving fewer interviews.
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“I was cancelled for, you know, speaking my mind,” he says, then pauses to rethink his words: “I was cancelled for being drunk and foolish in public. But that was something I was always allowed to do. No one gave a s--t [until I started to get famous].”
Caesar apologized for his comments a few days after his post and, in the years since, hasn’t shied away from reflecting on them further. But though the repercussions for him largely happened on social media, Caesar admits the whole episode deeply affected him. Sensitive by nature, it took him years to process his fear of being misunderstood. He’d been accustomed to expressing his thoughts freely, talking through big ideas with friends no matter how messy or half-formed they might be — an impulse that informs the big-hearted honesty of his music, but which has also gotten him into trouble at times.
“I’m literally my father’s son,” he explains. “My dad was the guy at sabbath lunch talking about how the government was going to put microchips in our arms. And I’m the same. If you get me riled up at a party, I’ll start talking about some crazy s--t. People roll their eyes, but that’s just the way we are.”
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Custom Brutus & Trent Nicklaus Munson T-shirt. Jacquemus Pants.Heather Hazzan
By the time the coronavirus pandemic hit, Caesar was already in a fragile state of mind. Case Study 01 had found a following but didn’t yield the same kind of breakout hits as Caesar’s previous releases. And after years on the road, he found himself in Toronto for the first extended period in years. Searching for peace of mind, he spent some time on his parents’ farm a couple of hours outside the city in Peterborough. But he no longer felt at home in the same way. He tried moving to Los Angeles, closer to the heart of the music industry, but didn’t feel entirely comfortable there either, especially as a single person. “I found it too isolating,” he says. “It’s like, you’re in your car or you’re in your house.” (He now lives in Downtown Manhattan.)
During this transitional period, Caesar ended up scoring the biggest hit of his career: when he co-wrote and guested on Bieber’s 2021 track “Peaches.” They worked on the song remotely, Caesar says, but he’s since spent time in the studio making music with the star singer; Caesar co-produced, co-wrote, sang backup and played bass on “Devotion,” off Bieber’s just-released album, SWAG. “He can sing his ass off,” he says. “He’s also so open and kind and generous. I can spot a fellow Canadian when I see one.”
In 2022, after being independent since the start of his career, Caesar signed his first major-label deal with Republic Records for his third album, Never Enough. It was the first time he’d broken off from the Golden Child Recordings team that had guided his career from the start.
“I was almost sheltered,” he admits. “I had never worked without them. They were like my career parents.”
Caesar is vague about what happened next, but he says he was naive, taking some people at their word that he shouldn’t have. “The music industry is awful and most people are awful,” he says. He sought out new management and realized that, as an artist without a strong business sense of his own, he needed to surround himself with people he could trust. “I’m open to the world, and that’s how I write songs,” he says. “But that makes me a sitting duck for anyone who wants to feed me faulty information.”
In 2023, he released Never Enough, which produced his biggest album chart success thus far, peaking at No. 14 on the Billboard 200 and No. 6 on Top R&B/Hip-Hop Albums. It was warmly received, with critics praising Caesar’s breathtaking vocals as well as his blend of experimental production and introspective lyrics; it also led to his biggest shows yet, including arena dates in both his hometown of Toronto and his adopted one of New York. But for Caesar, something still didn’t feel right.
“I feel like [on Case Study 01 and Never Enough] there was this undertone of anger,” he admits. “Growing up, I was angry about so many things, and it was inappropriate to express it. And so it would come out in the music.”
Heather Hazzan
He’d been searching without luck for a reconnection to the earlier days of his career, when it was less influenced by business concerns or expectations of critical or industry approval. Toronto, too, had changed. Some of the spots most meaningful to him were gone, replaced by shimmering glass condos. Unsure how to live in the city, he’d return to old haunts like Apt. 200, the trendy DJ hotspot he frequented when he was 19 — and find himself still surrounded by 19-year-olds.
“I felt like a stranger in my own city,” he says. “It actually made me feel really sad.”
Seeing most of his high school friends grow up and have kids made him acutely aware of just how different his own lifestyle had become. He’d never wanted children or the traditional trappings of adulthood; still, he felt like he needed to make a change.
“It’s not like I’m going to stop making music. This is what I love to do,” he says. “It’s more about trying to grow up and take accountability for all the ways that I’m selfish or push people away or…” He pauses. “You know, you cut people off if they don’t fit into your idea of life. But that’s not the way family works. And family is, like — it’s the whole point of life.”
On the day we speak over Zoom, Caesar is at his place in New York, fresh from a spate of globe-trotting that included stops in Cairo and Ethiopian capital Addis Ababa with fellow artists Mustafa, Rex Orange County and Tamino.
Mustafa, also a Canadian singer-songwriter living in the United States, has become one of Caesar’s closest friends and collaborators. Caesar joined him last year for the Artists for Aid concerts in London and New Jersey benefiting humanitarian efforts in Sudan and Palestine, and he credits Mustafa with helping him connect his music to something bigger than himself and embrace a cause that he once felt too nervous to talk about. “Free Palestine,” he now says proudly.
Together, Caesar and Mustafa work through their thoughts with their music, something they’ve done at informal pop-up shows around the world. “It’s really not even for the fans. It’s for us on the stage,” Caesar admits. “Sometimes I feel like the fans are like, ‘Just shut up and play “Get You.” ’ But this way we get to talk and figure out our ideas in public. It contributes to figuring out who we are and what we want to write about.”
One such show in Stockholm led to the Never Enough standout “Toronto 2014.” An older song originally written for Mustafa’s 2021 debut, When Smoke Rises, the new version took shape after the two worked through it onstage, exploring their complicated feelings surrounding nostalgia, innocence and the passage of time.
This time around, in Ethiopia, Caesar had other heavy subjects on his mind. “I didn’t even know exactly what I was looking for, but I just knew whatever I’m looking for is probably there,” he recalls.
Caesar was drawn to the country for several reasons: its historic connection to his own Jamaican heritage; the fact that it’s a Christian nation (Caesar visited the Church of Our Lady, Mary of Zion, believed by some to have held the original Ark of the Covenant); and especially the fact that it’s the only country in Africa that was (aside from a brief military occupation by Italy) never colonized. “It was really cool to see a culture of Black people whose culture is unintruded upon,” he says.
Since the response to his “cancellation,” Caesar has thought deeply about colonization, systemic racism and historical wounds. “That idea of, ‘Let’s all come together,’ on some Martin Luther King s--t — after that situation that I found myself in, I realized, ‘Oh, that’s not real. That’s not possible. There are too many scars.’ ”
Lately, he’s also thinking a lot about religion, a subject he’s long explored in both his personal life and his music. His first EP was titled Praise Break, a reference to both the traditions of gospel and his own break from practicing his faith.
Now, on his forthcoming new album, he’s exploring how to reconcile his religious upbringing with his more nuanced search for meaning as he matures. “Who’s going to be my Jesus?” he sings in the softly strummed “Moon,” which he debuted at the Mod Club show.
Caesar has been working on Son of Spergy for two years, piecing it together in sessions in Oracabessa, Jamaica, Rue Boyer in Paris and Electric Lady in New York. Evans and Burnett are co-executive producers, along with Mustafa, who Caesar credits with helping him break out of his usual shyness to form connections with other artists. The result is an impressive pool of collaborators on the album, including Sampha, Clairo, Dev Hynes of Blood Orange, Justin Vernon of Bon Iver, Rex Orange County, Yebba and more.
He describes it as more guitar based and "songwriter-y," with a lot of gospel influence – not just in the sound of the music, but in its spiritual soul searching.“It’s about religion, but more importantly, it’s about my father,” he says of the album, whose title references his father's nickname. “In your childhood, your father is a lot like God. He’s the person you fear the most on earth and also the person whose love and respect you desire more than anyone else on earth. It’s the source from where all your blessings come.”
As he’s found himself in compromising positions over the last few years, Caesar’s sure that something has been protecting him. And as he’s had to make hard decisions, he’s realized that, even when he was presenting himself as an atheist, the values he was raised with still guided him.
“I always compare it to a computer operating system,” he explains. “My parents raised me with Christianity. If I’m a Mac computer, I can’t just wake up one day and decide to run Windows. That’s not who I am. My best bet is just to update the macOS.”
As he figures out how to update his own programming, discovering kindred spirits has been helpful — above all, Tyler, The Creator. Caesar collaborated with the rapper on 2024’s Chromakopia, receiving official credits as a writer on three tracks and a singer on four. But his fingerprints are all over the album — both in its warm vocals and its introspective existential themes.
The two artists bonded in and out of the studio, often sharing long conversations about the future. “I’ve been making music since before I had pubic hair,” Tyler says of their similar starts in the industry. “I got famous at 18, 19 years old, so my version of the real world is so completely different from most. Now I’m at a place where I’m really thinking about kids, my back, if I’m going to be doing this for a long time or where I’m going to live outside of home and why I’ve stayed in L.A. for so long. I think me and Daniel are kind of in a similar place with that.”
Onstage at Tyler’s Camp Flog Gnaw last year, the artist credited Caesar with getting Chromakopia finished. A musical maximalist, he relied on Caesar to weigh in on production and arrangement details and tell him when too much was too much, which took some getting used to.
“He’s a genius. He’s such an important voice for our generation,” Caesar says. “I felt like, ‘Who am I to tell you what you should do?’”
Now he credits Tyler with helping him break out of his soft-spoken suburban Canadian humility to confidently pursue his musical vision at all costs.
“I think he knows he’s so f--king ill now,” Tyler says. “I think he kind of knew it… but now he’s walking around like, ‘Yes, my d--k is 15 inches.’ That’s that energy.”
That experience has also made him more intentional about the people with whom he surrounds himself. After finishing the album cycle for Never Enough, Caesar reached back out to Evans and Burnett — his first collaborators, whom he knows will always have his back — which has made him feel grounded again in the business. Along with Devante Browne (who he’s also known since childhood) and manager Marc Jordan of State of the Art in L.A., the two are now co-managing Caesar again.
“I did all these things, made all these changes and realized — I had it right the first time,” he reflects. “I just had to sit my ass down and take the lesson.”
His performance at the Mod Club felt like it cemented their reunion. There was a lightness and ease in Caesar’s demeanor, the way he sang, in his boyish grin.
“Starting was the best part,” he tells me. “It feels like a hobby. Then it becomes your job and it’s corrupted by commerce. That’s not why I started making music. I started because I had something to say. I had feelings I needed to process. Now it just feels pure.”
Additional reporting by Kyle Denis.
This story appears in the July 19, 2025, issue of Billboard and also appears on Billboard U.S.
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