Daniel Caesar holds himself to a predictable and impossible standard: “perfection,” he says. 

It explains the title of his upcoming third album, NEVER ENOUGH (out April 7), which is the Toronto native’s first release since signing with Republic Records two years ago. It will also usher in a new, more alternative sonic chapter for the 27-year-old singer-songwriter. “If I was a punk artist, then I would want to be something else,” he says. “It’s really just not wanting to be boxed into anything.” 


Caesar veered close to perfection in the early days of his rise, entering the industry with his 2017 debut, Freudian, which positioned him as R&B’s burgeoning golden child from north of the border. Freudian landed two singles on the Billboard Hot 100: “Get You,” featuring Kali Uchis and “Best Part,” alongside H.E.R. The latter — one of three Adult R&B Airplay chart-toppers for Caesar — earned him a Grammy Award for best R&B performance (“I crossed that off much sooner in my life than I ever thought I would,” he says of the win). 

By year’s end, he landed two songs on former President Barack Obama’s favorite tracks of the year list. Perhaps most impressively, Caesar did it all as an independent artist working alongside a tight-knit team of fellow Canadian creatives and close friends. Together, they founded Golden Child Recordings after attending a handful of label meetings and realizing they already had all the resources to succeed. “The music was making some money, so we just kept reinvesting in ourselves,” says Caesar. “I’d never made any sort of music without them. It was everything I knew.” 

Daniel Caesar photographed March 16, 2023 in New York.

But Freudian’s follow-up, 2019’s Case Study 01, struggled to replicate its predecessor’s success after Caesar shared controversial opinions on race relations on Twitter and Instagram Live. During one particular livestream, where he said he was drunk, Caesar questioned why the Black community was being “mean” to white people, saying, “That’s not equality.” 

The subsequent backlash took him by surprise, and Caesar says he underestimated the reach and impact of his opinions. “I understand why it happened. I understood it then as well. I’m just so combative, and I didn’t think that I was wrong,” he admits today. “I was trying to move through the world [according to] how I think it should be and not how it is.” 

It’s his comfort with vulnerability that makes Caesar’s introspective take on music feel like a deep sigh of relief, each sonic exhalation breathing new life into the R&B space. It is also what made his fall from grace an even harder pill for fans to swallow.  

“I try to keep my privacy and not to speak too much to the public [out of] fear of being misunderstood,” he explains today. “My best mode of communication is music.” 

Daniel Caesar photographed March 16, 2023 in New York.

Despite the overshadowing controversy, Case Study further cemented Caesar’s avant-garde take on R&B and proved a cohesive, replay-worthy body of work that boasted a No. 1 record on the Adult R&B Airplay chart, the Brandy-assisted “Love Again.” 

Less than a year later, as the pandemic hit, Caesar took refuge at the “middle-of-nowhere” 36-acre farm he had bought his parents, located in a town two hours outside of Toronto. It was there that the Bajan-Jamaican artist began reconciling the last few years of his come-up — and contemplating how to advance his career. 

Like many, Caesar maintained sanity by picking up quarantine hobbies, such as chess and studying Paulo Coelho’s The Alchemist. He also went back to work: In 2021, he scored a Hot 100 No. 1 for his feature on Justin Bieber’s smash “Peaches” (alongside Giveon), and last year, he featured on Omar Apollo’s “Invincible.” 

At the same time, he was focused on NEVER ENOUGH. Unlike the star-studded Case Study 01, Caesar returned to what he knows best: working both independently and with Toronto collaborators like badbadnotgood, Jordan Evans and Matthew Burnett and even his little brother, Zachary Simmonds, who co-wrote and co-produced “Valentina.”  

The tracklist went through three iterations, with Caesar saying he initially felt anxious ahead of the album’s release. But he found reassurance in remembering why he makes music in the first place: “For me,” he declares, “it’s literally just to get these feelings off my chest. To make myself proud.” 

Caesar’s demeanor is refreshingly self-aware. As he sits at a desk in his sunlight-soaked Manhattan loft, he weaves through the questions that kept him up at night and inspired the 15-track set. “If you dangle enough money in front of me, will I change my belief system? Can a woman make me change my world view? Or the proposition of sex? What do you fold on yourself for?” he asks rhetorically. “I’ve [folded] on myself and it’s hard. Those are the things that I beat myself up over.”  

NEVER ENOUGH centers the introspective bars, soothing blend of woozy guitar and hypnotic harmonies fans have come to expect from Caesar, with hints of cross-genre influences. Phrases like “Do I titillate your mind?” do just that while suspended chords and R&B structure on tracks like “Always” and “Cool” resonate with purist listeners.  

“When people ask me what kind of music I make, I always say R&B. Just to simplify things,” he says, adding that he senses a lack of innovation in the space. Luckily at Republic, Caesar has even more resources to continue expanding the genre space. 

“I was finding it hard at Golden Child to be a record exec and an artist at the same time,” he says. “This was something I needed to do for myself for my development. I was like, ‘If I don’t do it, it’s because I’m scared.’ And I hate living in fear.” 

Daniel Caesar photographed March 16, 2023 in New York.

Caesar met with eight or nine labels, saying he considered Columbia and Warner before signing with Republic. “Republic was actually the label where I said, ‘I would never go there,’ ” he recalls. “It’s just such a big label. They have all the biggest acts. I would be the least important person there.” But after meeting with label founder/CEO Monte Lipman and then-senior vice president of A&R Julian Swirsky, it became clear the label’s help would allow him to do exactly what he wanted: focus on his craft — and his fans. “I felt for a while, especially over [the pandemic], like I didn’t have a relationship with them, or it was severely fickle,” he says. “Like they love the songs, but they don’t care about me — which is completely reasonable. Why should they care about me?” 

To reconnect, he met fans where they were: from the favelas of Brazil during Carnival (a country where he realized he has a large listenership) to his newly launched Discord channel (“It’s some Gen Z sh-t for real,” he jokes). He’ll celebrate the album’s release by kicking off his intimate North American and European underplay tour, One Night Only: An Evening With Daniel Caesar, which will begin April 7 in Los Angeles. 

For Caesar, NEVER ENOUGH chronicles his path to becoming his own man while finding a balance between longtime trusted collaborators and welcoming well-established executives into the mix. “I always tell people, ‘I don’t believe in God. I believe in myself and the people around me that I love,’ ” he says. “I believe in our capabilities.”

A version of this story originally appeared in the April 1, 2023, issue of Billboard.

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