The narrative of a meteoric rise and fall is compelling and tidy, it’s one we’re drawn to in artists both real and fictitious. But what happens when someone rockets to prominence, stays at the top, and realizes they might not love the view? That’s more complicated, and that’s what Daniel Caesar is going through.
The Toronto-based musician born Ashton Simmonds achieved critical recognition following his 2015 EP Pilgrim’s Paradise, later becoming a streaming darling and festival mainstay with 2017’s Freudian. He’s been nominated for nine GRAMMY awards, winning Best R&B Performance at the 2019 GRAMMYs, and has been part of several multi-platinum records. But achieving all of that by 27 has left the ever-philosophical singer at something of a crossroads.
"Plaques are boring to me and award shows are boring to me. I don’t enjoy sitting through the GRAMMYs," he tells GRAMMY.com. "I was looking for a feeling like, I respect myself and I know I did something and I can feel that the respect from my peers and the people who enjoy it is real."
That realization is reflected in the title of his latest LP, Never Enough, which comes nearly four years after 2019’s Case Study 01. The creative process began in quarantine when Caesar was holed up in his Toronto home. The music he wrote in that period of relative isolation was somber, and when his younger brother visited, he told Caesar that though the songs were good, "It doesn’t sound like you’re enjoying doing this."
Caesar shifted his focus, going for more of a "pill in the peanut butter" approach where some of the weightier concepts were cloaked in buoyant, elegant soundscapes. But this is a Daniel Caesar record, and it wouldn’t be complete without frank self-examination, psychological jargon, and morally gray tales of romance and fame. The album’s most compelling track, "Buyer’s Remorse," is built around a line that Caesar had been ruminating on: "I guess I got what I paid for," which he uses as a lens to explore both his relationship to celebrity and to his love life.
"I'm envious of people who just let life happen to them, because all the bad things, they can just blame on the devil and all the good things they get to thank God and they’re just a victim of their life," Caesar says. "But for me, every time I do something I’m like, 'Oh s—, I made that happen and I made this thing happen.' By taking responsibility for all your own actions, you are now responsible for all the misery in your own life and all the hurt caused to other people."
His honey-sweet voice is still a major draw, as he glides across songs like "Homiesexual" and "Superpowers" with Olympic-level grace. Never Enough also sees Caesar progressing and experimenting sonically on the psilocybin-y "Do You Like Me," with its distorted vocals and groovy guitar, as well as "Shot My Baby," with its serrated riffs and bristling drums.
Ahead of the release of his third album, GRAMMY.com caught up with Daniel Caesar in New York to discuss how success at an early age forced him to reconsider his goals, the much darker album he scrapped before Never Enough, and his thoughts on the sentiments behind toxic R&B.
A consistent theme across songs like "Toronto 2004" and "Cool" is your sense of nostalgia and yearning for when things were all ahead of you. I’m curious, are you generally a nostalgic person or is that a sensation that has come upon you in the last few years?
Yeah, I think it’s come upon me. For most of my life, my mother would always tell me [that] I was always in a rush to grow up, as so many of us are. I guess through COVID I got to this place where I was like, "Oh s—, I’m old." Like today, at lunch, I stood up really fast at the table and I felt my knee do a thing, you know? I hate that feeling so much. That’s a very literal interpretation of it, but I’ve been feeling nostalgic, missing being younger.
This time passed during the early part of the pandemic doesn’t feel like it counts, but it does. You can’t recoup it on the backend.
It’s so insane. Just two years feels like [it was] down the drain. It was the worst time in my life, but then it did become the best time of my life.
What changed?
I wouldn’t have taken that time to stop had I not been forced to. So much of my life had become about doing what I want when I want to do it, and that was one of those times where I couldn’t do what I wanted. I’m not used to that. I’m always a get-around-the-rules kind of guy, so, I couldn’t. [I] had to face things and work through things.
When I was in COVID just in complete isolation, I set up a studio in my guest house and I put whiteboard paint all over the walls. I think everything I made from then is still up. The apartment is still as I left it and it looks like a madhouse.
You were drawing on the walls?
Yeah. I wrote out a list of rules that I had to abide by, little phrases. I just went nuts and that’s how I set out. I remember when my little brother came back home, he came in there and saw what I was up to, and he said something that really [stuck with me]. I was completely isolated and I was really going through it. I was showing him the music and he was like, "Yo, this is sick, but it doesn’t sound like you’re enjoying doing this. It all sounds like you’re sad and laboring through this." He was 19, 20 at the time. He’s fresh, he’s green, he’s just like, "You don’t sound like you’ve been in here vibing." It was all slow driving in-the-rain music, you know?
I got to the end of making the album and I was like, "It’s not good enough yet." It was how I was feeling, I wasn’t feeling happy, so it was an honest representation. But I wondered, is that what I want the world to feel? Is that what I want to give the world? So, then it turned into this more ambiguous, "I’m just going places and vibing things out and the album is creating itself." I made three albums in the process of making this album.
When you say the three albums, were each of them very distinct in terms of the tone? Was there an optimistic album, this darker one, or was it all different moods interspersed?
The first was dark. The second was a refining of the first one, I guess. It was like a gradual arc, but it was dark to dark themes dressed up pretty and happy.
The Trojan horse thing.
The Trojan horse thing. Put the pill in the peanut butter. I didn’t want to be negative, but at the end of the day, I can’t deny that negativity plays a role in my life, and sometimes that’s what drives me to write a song.
Especially being in isolation, I was dealing with love where the honeymoon phase had come before COVID. I had gotten separated from my love because she lived in America and I lived in Canada, so this album is not about falling in love, it’s about the flipside of love.
The song that really stuck with me when I was listening was "Buyer’s Remorse." That concept gets explored in music in the sense of "Oh, being famous isn’t what I bargained for," but to hear it being very literally applied to a romantic relationship was interesting, because most people aren’t that frank about it.
That one we did in New York. Omar [Apollo] was there and Sean Leone was there. I just had the line "I guess I got what I paid for" and I dunno what was going on around the time, but I was going through this lust phase. Being heart-hurt, being in love — I’ve always been hyper vulnerable and growing up you realize that if you carry yourself super vulnerably with all women all the time, [you’ll get hurt].
It’s like, This way I’ve been living my life isn’t conducive, it’s not safe. So let me just separate love and lust. I’ve been in love before, but at the same time, I have this sexual attraction to all these different women, strippers and prostitutes. It’s fine, you separate the two things and then you have them mastered. I was going through this whole era of transactional sex. I don’t love this person, but we’re gonna go on a date and I don’t have a crush on you, but it’s sex devoid of love.
You have this one interaction and then you go your separate ways and you maybe never talk again or don’t see each other for months.
And it’s not just about that, but that’s kind of where [the lyric] came from, "I guess I got what I paid for." It might not be apparent all the time, but I do have a strong self belief and feel like I am in control of my reality. I make things happen. I make an action, then something happens, and I don’t always like the consequences.
I’m envious of people who just let life happen to them, because all the bad things, they can just blame on the devil and all the good things they get to thank God and they’re just a victim of their life. By taking responsibility for all your own actions, you are now responsible for all the misery in your own life and all the hurt caused to other people.
There are downsides to that approach, too, because you can’t run around pretending you have no agency.
It’s tricky. Being human is tough, it's just coping. What’s the best way I can be human to cope with being a human? I wanted to change my life so badly at one point, I was like, "Let me just take responsibility for everything." I don’t want to sound pious, because I feel like I can very easily skirt responsibility for things off myself.
Every time in an interview I say something and then I think of four examples of me doing the opposite, so I’m like, "Oh, I’m a fucking phony." It makes it hard to speak sometimes.
Your rise in music coincided with the boom in toxic R&B, which indulges in that "I can’t help myself," sentiment. But I feel like when you write a song about having done something wrong, there’s a real sense of turmoil and trying to figure out how you move forward.
I think why it connects is because there’s a certain level of religious guilt to everything I do and say. It’s a real self-chastisement, so it’s not for aesthetics. I admire the aesthetic of "Ah f—, girl. I’m such a bad guy." It’s not like I don’t engage in that sort of [toxic] behavior, I just have a different psychology when I’m doing it. I just do it in a different way so you don’t even get the glorified sexualization of that behavior.
I just feel bad about it and I don’t even weaponize it. That’s not even like, to be pious or whatever, it’s just like ick. It is what it is, but it’s interesting.
Does the songwriting process allow you to work through things emotionally?
I’ll go into a song thinking something and then, a lot of times, what I’m thinking is reflected in the song. Other times, I do the song just vibing and then I’m like, "Oh s—, I didn’t even know that I thought that." I found it after.
I go into an album thinking I know what I’m gonna sing about or write about, and then ¾ of the way through the album, it always changes. Every time I pick a title starting an album, I know it’s gonna change, but I pick it so that I have a bearing. I can’t stick to a program, so I know it’s gonna tell me what it is. With songs, too, I learn about myself by writing.
Was there another title before it was Never Enough?
It was called Pseudomutuality at one point.
"Pseudomutuality" is really interesting because thematically, it fits with the first two albums, but I think some of the most interesting stuff on the record is about your relationship with your audience. The "Vince Van Gogh" song is fascinating. Why was he the figure you wanted as that tragic artist archetype?
Van Gogh’s art became valuable after he died. I thought about my last album, which was about death. I think about death all the time, and it was a decision that I was going to figure out more than just making songs.
That’s another big struggle. I say all the time, there are so many things I’m really bad at, but when I need a boost of confidence, I think about the fact that I’m really good at making songs.Marketing is a part of this job that I don’t enjoy. I don’t like the fact that I have to figure out TikTok. I’m still working, I’m still figuring it out, but "Vincent Van Gogh" was [saying] it’s not gonna be like "Oh that guy’s dead? He was f—ing great." I want to be here, I want to experience it.
There’s also a point, I can imagine, where you don’t want to feel that sense of responsibility.
All the time. I’m an artist and I’m inconsistent and I flip flop emotionally. Given the music business, [I’ve been] having this conversation the past year, like "Yo, can you please just be consistent." We were just talking about this earlier, like, "Yo, can you pick an outfit you like and wear it every day so when people think about this outfit they think about you" And I’m like, "Yeah, yeah, yeah." And then tomorrow I’m gonna wake up and put on shorts and flip-flops and socks. I’m just working through it.
Do you feel like at this point, having gone through the last couple of years and making this record that you’re at a more sustainable place? It sounds like you were pretty burnt out prior.
Yeah, I was burnt out. It’s still tough all the time, but I’ve proven to myself that at least I’m not gonna give up. The horse is gonna have to buck me off, I don’t even know if it’s in me to bow out gracefully and get off the horse.
I wonder if you had released that darker first iteration of the album and had to deal with that, maybe it’d be hard for that to get you back to the place where it motivated you to keep making music.
I don’t think so. I think, regardless, I would’ve wanted to make [something] again. I don’t want to sit here and pretend like I don’t want commercial success. That’s another big part of why I’m fighting; that’s why I’m not only focusing on things I enjoy. I’ve proven to myself that I can make songs and make a comfortable living, but I want to push myself. I also want commercial validation, but if no one buys the album, I’m still gonna make another album.
It’s all about how you frame it. If you say "I want plaques," that’s cynical. But if you say "I want a large number of people to connect with this and keep playing it the way they did with [the last two]," that’s understandable. You want to reach a wide audience and have them dig it.
I got a plaque just the other day. Plaques are boring to me and award shows are boring to me. I don’t enjoy sitting through the GRAMMYs. I was looking for a feeling like, "I respect myself and I know I did something and I can feel that the respect from my peers and the people who enjoy it is real."
After getting the first GRAMMY, I was depressed. I was like I achieved that thing. I thought it would be way harder to get this. It’s like, okay you’re in the club, you’re on the world stage of making music and can make music with other really good people. You’re not an amateur.I can’t really express it through words, but there’s a certain feeling I’ll probably never get , which is why I’ll keep making albums.