The Philadelphia native got his start rhyming earlier in life, spitting his first bars in grade school during an afterschool program. By his early teens, he was an avid freestyler and could often be heard rapping on the back of the bus on the way to football games. He’d get just as much attention from his punchlines as his quarterback play. And then things changed in the blink of a rhyme. Drewboy had begun freestyling regularly on his Instagram account. On July 13th, 2019, he delivered a series of scorching bars in what became a memorable live session. “It was going crazy,” Drewboy remembers of his follower’s reactions. “The next day it had a million views,” he adds, recalling how he woke up to calls telling him he went viral. “And in one day I gained 75,000 new followers.” Drewboy pounced on the opportunity and reworked the freestyle in order to release it as a single titled “Close Friends.” The track was a hit and soon he was fielding phone calls from Meek Mill, Rick Ross, Snoop Dogg and major record labels. He also scored a prime slot on local radio station Power 99’s yearly celebration, Powerhouse, where he showcased his energetic stage set. Drewboy ultimately opted to join forces with Team Xcluzive Entertainment and producer Tommy Brown (Arianna Grande’s “thank u, next”) ultimately signing to his label, Champagne Therapy. Shortly after that, they formed a partnership with Island Records to release his debut project, The Personality Mixtape.