Chicago’s Calboy shows why he’s the envy of aspiring rappers everywhere on Wildboy | Concert Preview | Chicago Reader

Chicago’s Calboy shows why he’s the envy of aspiring rappers everywhere on Wildboy 

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G.MOODIE/Audible Treats

Scroll through the first 20 of Soundcloud’s 50 most popular tracks right now, and you’ll find songs from three Chicagoland MCs: Juice Wrld, Polo G, and Calboy. The song in the top 20 with the most total plays is Calboy’s “Envy Me,” with more than 66 million since December. And those numbers are just for the version Calboy released after signing to RCA and Polo Grounds in fall 2018—the “Envy Me” video had been on YouTube since August, and now has more than 113 million plays there. The melodic, bittersweet tune has inspired a dance challenge on video-making apps such as TikTok and Triller, and it’s provided a milestone for the newest class of successful Chicago street rappers—a loose cadre that includes Lil Zay Osama, El Hitta, and the aforementioned Polo G. These artists’ lyrical prowess, entrancing pop hooks, and proclivity for singing help their darkest stories go down smoothly, which might be part of why they haven’t provoked the kind of media hysteria that greeted Chief Keef in 2012. Calboy’s major-label debut, May’s Wildboy, fills out its lyrically sorrowful, melodically irresistible songs with guest spots from a team of big-name rappers, including Lil Durk and Meek Mill; their variety of vocal textures breaks up his smooth performances and ensures the material doesn’t blur together.   v

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