 Prior to joining "Cracked", Pinkerton served as the managing editor of NationalLampoon.com, the website of the national comedy and film brand.Jay Pinkerton initially registered his website, Jaypinkerton.com, to be a portfolio of his comedy and artwork.Afterwards, Pinkerton joined the forums of the Internet humor website "Pointless Waste of Time" (PWOT), and took the attention of the site's owner, David Wong, with whom Pinkerton worked on a now-defunct satirical news commentary, the "News Skim", and other comedy articles.