First you saw him: a 16 year-old Indonesian kid, mean-mugging in a pink polo and a fanny pack. Then you heard him: a cold-blooded rap assassin, his voice deep, croaky, and remorseless, as if baptized in brown liquor: “Rogue wave on you niggas, no fail when I hit 'em/ Every time I see a pig, I don't hesitate to kill him.” The inter-sensory dissonance one experienced when watching Rich Brian’s (then known as Rich Chigga) “Dat $tick” for the first time was so great that the music video was destined to go viral. “Dat $tick” had as much fidelity as Slim Jesus’ “Drill Time,” but unlike Slim Jesus, Rich Brian possessed a self-awareness that injected his rap cosplay with the element of satire, and by extension, intrigue. Seriously: who was this kid? The promising string of singles that followed – "Who That Be,” “Seventeen,” “Back At It” – combined Brian’s one-of-a-kind voice with his surprising knack for producing grimy trap beats, with cover art indebted to his absurdist internet comedy roots. Since then, he’s been determined to evolve his sound, to move beyond the status of novelty act, and to speak more candidly on his transition from homeschooled teenager working in his mom’s café to jetsetting rapper living 9,000 miles away from home. At the beginning of 2018, before he put out his debut album Amen, he formally changed his name to Rich Brian, eager to jettison some problematic baggage he still carried from his initial foray into rap. Listening to his new album The Sailor, it’s hard to believe that “Dat $tick” ever existed. The album takes many of its cues from rap heavyweights like Drake, Kendrick Lamar, Frank Ocean, and post-Cherry Bomb Tyler, the Creator. The beats are often structured around sun-kissed guitar and dramatic John Williams orchestral strings. Brian sings as much as he raps; when he raps, he no longer deepens and intensifies his voice like he’s trying to convince the cashier at liquor store that he’s of age (he’s still only 19). As he tackles larger themes – like sex, relationships, family, celebrity, and sex again – the charm and tension that made his earliest work compelling evaporates. In a recent interview with Complex, Brian explained the two-fold concept behind The Sailor: it’s about 1) his personal journey moving to the United States to pursue a rap career, and 2) immigrants’ hope for a better life. While he seldom touches on the latter theme in the album, the former theme offers fertile ground for flexing and reflecting on how far he’s come. On “Curious,” he’s overcome with homesickness, missing his mother and worried that she’s worrying about him. “Kids,” which he personally played for the president of Indonesia, is a triumphant, arms-spread, momma-I-made it anthem dedicated to young dreamers: “Everyone can make it, don’t matter where you from.” Brian rides for his home in the album visuals, too. A short video featuring the title track features him rapping from the middle of a large, formal family portrait, while the “Kids” video is an homage to his hometown of Jakarta. His wide-angle takes on his career offer some of the most resonant moments on The Sailor. When he acknowledges that he is, by far, the biggest rapper to ever come out of Southeast Asia, his music takes on a greater meaning. While Brian dedicates a few songs on The Sailor to soberly dissecting and reliving a failed relationship, he is generally much more interested in articulating his feelings about sex – namely, his desire to have it at all times. He blurts out some groan-inducing, overly horny lyrics in what feels like every verse. In Brian’s mind, sex is essentially transactional, and his penis is actually a gun. He told Dazed Digital that he hoped his ex-girlfriend would be impressed with The Sailor, and with one-liners like “Aim my dick and I shoot her abdominals,” how could she not be? The thing that softens the blow of Brian’s grotesque blowjob bars is the elegant vocal production of Bekon, best known for his work on Kendrick Lamar’s DAMN. (The similarities between the second half of The Sailor title track and DAMN.-opener “BLOOD.” are… striking). Bekon’s own pillowy vocal interludes are all over The Sailor, and his fingerprints appear on some of Brian’s more gorgeous melodies, like the chorus of “Where Does the Time Go,” where the ascending line “I cannot fuck with these hoes/ they don't care about me” achieves total weightlessness. The Sailor represents Rich Brian’s biggest artistic leap yet, but he’s still searching for his sound. His attempts to transform virality into longevity have dulled his subversive edge (this is a good lesson for Lil Nas X, another memelord born in 1999). Brian’s subversiveness is inevitably tied to his status as a teenage Asian outsider infiltrating and transforming the global rap establishment. “You big in your city, I'm the king of a continent” is a big-time flex – one that, even though it's not wrong, he’s still growing into.