Like many viral rap stars, Rich Brian initially treated his music like just another bullet point in a personal-brand sales pitch. The outlines of that pitch are well-known by now: Young Chinese-Indonesian teen Brian Imanuel learns English on YouTube, dubs himself Rich Chigga, goes viral with a song called “Dat $tick” on which he throws around the n-word with startling nonchalance, rhyming about scenarios with which he almost certainly has no firsthand experience (e.g. shooting cops) while wearing a large fanny pack. As a listener, your choices are to write him off as a troll or enjoy his competent, syrupy flow while trying not to dwell on the problematic specifics. If you’re really being honest, unpacking it all gives you a headache.

But that was three years ago. In the short time since Brian arrived as a polo-clad edgelord, he’s traded shock value for an actual career. Now 19, Brian is no longer Chigga, no longer courting controversy for clicks. His interviews reveal a hungry young man with a worldly perspective: “My goal is to go mainstream—partially because I really want to pave the way for Asian kids to be themselves,” he has said. His label, 88Rising, has become an undeniable part of the global pop landscape, with Brian as its biggest star and de facto ambassador. On his first album, Amen, he fashioned himself as a bridge between a new Asian underground and mainstream hip-hop, exploring his unusual place in the culture with occasionally deft observations. Mostly, though, he rhymed about the internet and partying. “Catch me chillin’ with Offset in a luau,” he rapped on “Attention,” an oddly plausible scenario.

The Sailor, Rich Brian’s second album in two years, is another bid to distance himself from his teenage output. By and large, it is a successful one: The Sailor is often charming, featuring some of the best music of his young career. Brian’s obsessions—life away from home, his search for emotional connection and sex—pop up all over the record, often as absurdist juxtapositions. “Bad energy, man, where my palo santo at?/Told her ‘Don't fuck me,’ ’cause this shit get sentimental fast,” he raps on the title track. (It should probably be noted here, though it may go without saying, that Brian has spent much of the last few years in Los Angeles.)

Brian’s flow is remarkably malleable, his production choices doubly so. He pulls off a Migos-indebted staccato on “Confetti.” On the family-and-friends anthem “Kids,” he channels Drake with the memorable boast: “You big in your city, I’m the king of a continent.” On “Yellow,” he references his backstory with a flex made for the times: “I did it all without no citizenship/To show the whole world you just got to imagine.”

While he used to gravitate toward trap, he now pulls in boom-bap drums, emo-rap choruses, even Spanish guitar and psych rock. His songs have become more melodic and bittersweet, losing the hard edge he never sounded particularly comfortable with in the first place. On “Drive Safe,” for instance, he invokes Kid Cudi, while “No Worries” glows with Frank Ocean moods like orange paint on a BMW M3. His most heartfelt tracks toe the line between confessional and saccharine. “Shouts out to the ones doin’ things/Everyone was afraid or unable to do, man/The world needs more of you,” he raps on “Curious.”

There are two moments on The Sailor that point to where Brian still might go. The first is RZA’s feature on “Rapapapa,” which is more motivational speech than verse: “Rich Brian was born to be rich with talents and balance/And the ability to face life challenges,” the Wu general intones awkwardly. “Represent your artistic intelligence/Your genetic pigment, your culture, your power.” It’s a goofy knighting of sorts, one wrapped up in the Wu-Tang’s complicated and storied relationship with Asian art. The second is the outro of “The Sailor,” in which Brian is confronted by a “mysterious young girl” en route to the corner store for passion fruit iced tea. She asks him a series of “whoa, dude” questions about life and death, the last of which is “What is a life if a moment can end in the blink of an eye?” Like all things Rich Brian, it falls between laugh-out-loud ridiculous and oddly sweet. But his career is getting harder and harder to dismiss.