While his stage name is a reference to Xanax, and he broke through with rhymes detailing his addiction to that prescription drug, Lil Xan raps about his recovery and sobriety, among everyday struggles and other issues related to his personal development. With an emphasis on hedonism, the Californian's early music fell somewhere between that of contemporaries like Lil Uzi Vert and Lil Peep, as highlighted by "Betrayed," the platinum single from Total Xanarchy (2018), his Top Ten debut album. Multiple EPs and dozens of singles preceded the arrival of his second album, Diego (2024), a positive-minded set with the rapper in lucid if typically casual vocal form. Born Nicholas Diego Leanos in Redlands, Xan first emerged in 2016 with songs like "Sorry" and "Center Fold," building an online following that would gain traction in 2017 with tracks like "Been Bout It," "Slingshot," and "Who Are You." A short EP, Xanarchy, appeared the same year. The rapper's Total Xanarchy tour, which sold out in five hours, launched in January 2018. Xan's debut album, also titled Total Xanarchy, arrived in April and featured guest appearances from 2 Chainz and Charli xcx, as well as Diplo, with whom he had just collaborated with on "Color Blind." Total Xanarchy debuted at number ten on the Billboard 200 and contained a platinum hit in "Betrayed." Although six years would pass before a true follow-up, Lil Xan remained fairly prolific between albums. In addition to numerous stray tracks, he released EPs such as Fireworks and the Chris Miles collaboration have a nice day. Diego, his independently released second LP, landed in September 2024 and was promoted with candid singles such as "NODA," "Used To," and "Won't Overdose." ~ Neil Z. Yeung

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Lil Xan

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