Big Jay Oakerson Big Jay Oakerson is one of the most beloved and easily recognizable comedians working today. His laid-back style and dirty delivery are the signature marks of his comedy. Jay’s career spans two decades, starting in Philadelphia as a “comic’s comic” before rising mainstream fame in New York. Constantly touring the country, Jay has been a part of some of the biggest comedy festivals including Moontower, Bonnaroo, RockStar Energy Drink's Mayhem Fest, Gathering of the Juggalos, Funny or Die’s Oddball Festival.