Daniel Caesar’s soul-baring debut, 2017’s Freudian, traced his journey of leaving home, finding love, and suffering heartache. On its experimental and existential 2019 follow-up, CASE STUDY 01, the Toronto-born singer-songwriter tried to understand the chaos of the world, confronting ideas of life, death, loneliness, and God. He’s shown his gift for taking heavy, complex themes and turning them into introspective songs about love, life, and everything in between, and they’re just as present on his third album, NEVER ENOUGH. Where CASE STUDY 01 came from a place of anger, and the uncertainty he felt about his career after making some controversial public comments about race at the time, NEVER ENOUGH finds the Apple Music Up Next alum reflecting on those doubts. “It was really aggressively seeking out truth and trying to learn about myself and about the world in which I live, because I want answers,” Caesar tells Apple Music. “That’s the most important thing to me. I think I’ve been dealing, struggling a lot with my desire to know things versus my desire to be liked.” This internal conflict is a constant through line on NEVER ENOUGH, whether he’s navigating his romantic entanglements (“Valentina,” “Buyer’s Remorse,” “Do You Like Me?”) or the heartache that comes along with them (“Let Me Go,” “Always”). It’s all part of his look inward to find himself. On the acoustic track “Toronto 2014,” Caesar reminisces about the happiness he felt before his newfound fame, and his search to get back to that feeling: “If only I could find a way through space-time/Back to when I was happy being me,” he croons. His desire to express himself artistically while staying relevant is challenged on “Pain Is Inevitable” (“Now I’m a product that must a turn a profit/Something to prove I’m a god, I’m a prophet”). “Every day, I remind myself that it’s exactly what I ask for and what I fought for and what I suffered for,” he says. “And there’s always moments where I feel like I’m the victim of this thing, but at the end of the day, it’s completely within my control, and I can just stop at any point.” He also collaborates with artists like Ty Dolla $ign, serpentwithfeet, and Raphael Saadiq, who co-produced “Do You Like Me?” The idea of feeling “never enough” is his constant struggle: trying to balance confidence and insecurity. He deals with his self-doubts on the haunting piano ballad “Cool,” but quickly reaffirms and builds himself up on “Superpowers.” That’s further cemented on the album closer “Unstoppable,” where Caesar challenges his critics, asking, “And who’s gon’ stop me?/I’m unstoppable.”

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