Philly rapper Drewboy lived a literal overnight success story, posting a freestyle to his social media account and waking up the next day to see it had been viewed over a million times. His upward movement from there was just as fast, as he quickly signed on with an Island Records subsidiary and brought his effortless, fluid flows and party-ready production to the 2020 mixtape Personality. Drewboy was born in Philadelphia and was rapping as early as grade school. Throughout his youth, freestyling was his main focus, and he often freestyled to entertain his friends or kill time. After posting video of himself freestyling on social media for a while, his number of followers grew to the point where it seemed natural to pursue music more seriously. He reworked one of his social media freestyles into his first single, "Close Friends," and the song's popularity was driven by his growing social media following. Drewboy would briefly sign on with Rick Ross' Maybach Music Group label in 2019 and begin releasing tracks shortly afterwards, but that partnership was short-lived. After signing on with Island Records affiliate Champagne Therapy, Drewboy caught more attention with the joyous and energetic single "Bars Is Back" in April of 2020. Several other singles followed the same year, as did his first mixtape, Personality. ~ Fred Thomas