100 Best Albums Tyler, the Creator had always peddled in the personal: Even when he was the enfant terrible of underground hip-hop, his most provocative and irony-soaked albums still provided open windows into his anxiety and self-loathing. However, his fourth album, 2017’s Flower Boy, was the moment Tyler fully embraced his role as bloodletting diarist. The introspective album stripped away the shock and fully embraced expressions of lovesickness and loneliness, growing and blooming like the flowers that dot the art and lyrics. He emerges as a pan-genre auteur, as likely to spit rhymes as croon in a Pharrell-ian falsetto, landing somewhere at the intersection of hip-hop, neo-soul and chilled jazz. The metamorphosis resulted in his first platinum album and his first Grammy nomination, beginning a thrilling second chapter to his career. Lead single “911 / Mr. Lonely” is almost confessional in its self-examination, with Tyler musing on his trademark extroversion being a coping mechanism, buying cars to fill a void in his life, and basically yearning for someone to share it all with: “I’m the loneliest man alive/But I keep on dancing to throw ’em off,” he raps. “Boredom” is a more immediate look at seclusion, and “November” tackles a laundry list of insecurities over lush synths. “A lot of the songs just have questions, it’s just like, ‘How am I feeling today? What if I go poor again? What if it doesn’t work?’” Tyler said. “And then that’s how a lot of the songs just happened.” Vulnerable love songs like “See You Again” and “Glitter” had people speculating about his sexuality (he came out as bisexual shortly after the album’s release), but regardless of the specifics, they are both evocative looks at infatuation that recall Erykah Badu and Outkast. “Garden Shed”—part Stevie, part D’Angelo—features rubbed-raw guitar and lyrics about holding a secret inside, with Estelle singing lines like “Don’t kill a rose before it could bloom/Fly, baby, fly, out the cocoon.” In many ways, Flower Boy was prescient about where music was going as a whole, thanks to early appearances from emerging bedroom-pop star Rex Orange County and future hitmakers like Steve Lacy and Kali Uchis. Though Tyler surrounds himself with a packed guest list of friends (Frank Ocean), heroes (Pharrell Williams) and rap superstars (A$AP Rocky, Lil Wayne, Schoolboy Q), Flower Boy is still a deeply personal statement from a one-of-a-kind artist.