Simpkins was born in New York City, to Monique Simpkins. He first appeared on TV when he was three weeks old. His first role was on One Life to Live where he shared the recurring role as John "Jack" Cramer. Simpkins soon started a recurring role as Jude Cooper Bauer on Guiding Light, in which he went on to be "Jude" for about four years. He guest starred in Law & Order: Criminal Intent, and a handful of commercials and print ads.