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 tim...