Jayaire Woods Credit: courtesy the artist

During the fading final notes of “Big Plans,” the cloudy closing track on Jayaire Woods’s August EP, Woodside Lane, a coterie of the rapper’s pals shouts the song’s succinct chorus a cappella. Woods is such a skilled songwriter his most potent verses beg to be shouted out loud even when you’re not listening to his music (thankfully I’m usually in the privacy of my own home when it happens to me). I could drive myself mad wondering why Woods hasn’t broken bigger, and I’m not the only one who thinks he should headlining theaters rather than playing small clubs—in 2017, peerless rap site Passion of the Weiss ran a lengthy piece on Woods that argued he’s Chicago’s most underrated rapper (he grew up in the western suburb of Bellwood). Woods’s easy-going melodic sensibilities and intimate lyricism led Atlanta’s Quality Control to sign him and put him on tour with label darling Lil Yachty in 2016, when Yachty was one of the hottest commodities in rap (that same year, Yachty made one of his strongest guest verses on the Woods full-length, Free the Fall). Last year Woods began releasing tracks through Layup Entertainment, whose cofounder, Stan Lane, produced Woodside Lane. He gives the 17-minute EP emotional weight from its first track, on “4 Walls” he effectively grapples with depression, failure, alcoholism, and a palpable sense of creative frustration—and that’s just in the first minute. Since the start of the year Woods has dropped a couple singles that show he’s as focused and perceptive as ever, including “Pretty Girls,” a full-hearted, slightly awkward tribute to women, who bear the brunt of toxic masculinity.   v