[4] Smooth left WBAI in July 2018 after the station hired Leonard Lopate, who was fired from WNYC for allegations of sexual harassment.

[2] Smooth, the son of a Jewish mother and a black father,[5] grew up in New York City, and attended Ethical Culture Fieldston School.

[2] Smooth began his career in media at 18 years old, when he founded a show called The Underground Railroad at New York's WBAI.

[7] He video blogs on a personal website called Ill Doctrine[8] which features Smooth's commentary on hip hop, politics, and social justice, such as in "Soulja Boy Presidential Debate Remix".

Smooth also occasionally provides music commentary on NPR,[9] He rose to prominence to mainstream audiences in 2008 when he released a YouTube video on his channel called "How to Tell Somebody they Sound Racist."