With lithe, emotive vocals and a willingness to dive into the depths of his most extreme feelings, XXXTentacion became a tragic symbol of SoundCloud rap. His emergence was tethered to controversy. At the same time his late 2015 single, "Look at Me!," was blowing up in 2016, he was sitting in jail after his ex-girlfriend accused him of abuse. By the time he was released from jail in March of 2017, he had become a full-fledged star, with an infamous mugshot and other controversies helping crystallize his status as a rap antihero.

Oscillating between alt-rock, synth pop, boom bap and even R&B, XXX's style appealed to fans from across generations and genres. All of his sounds were threaded by themes of aggression and despair while tragedy and sadness were always close by. His first album, 2017's 17, produced now-iconic songs like "Jocelyn Flores," a song made after a teenager who committed suicide after he briefly met her. The LP was RIAA-certified gold by February of 2018, and it was certified three-times platinum in 2023.

XXX continued his level up when he released "Sad!" in 2018. The synth-pop tune blended a top 40 melody with an emotionally sadistic premise: if the woman he loves decides to leave him, he'll kill himself. Dark, but hopelessly infectious, the track has been RIAA-certified diamond. Titled ?, the 2018 album the track belongs to has been certified five-times platinum. Despite legal issues, XXX continued to rise until he was shot and killed at Riva Motorsports on June 18, 2018. He was only 20 years old. Since his death, two original posthumous albums have been released, along with a soundtrack for the Hulu documentary, Look At Me, which is based on his life story.