Prior to starting Chortle, Bennett, who graduated from Oxford University, had been working as a local newspaper editor for the Informer group of free newspapers in Surrey and West London.[1] He started the site after the newspaper group expressed a lack of interest in running a website. After considering his areas of interest, he decided to start a comedy site, since IMDb and Empire already covered the market for film, and there were numerous music websites available.[1]
The site received some early support from investors during the dot com boom which led to Bennett working from offices in Brick Lane, London. After that company went bankrupt, Bennett continued the site, as he felt the comedy section of Time Out was not covering the breadth of comedy in the city in sufficient detail. However, the site was not financially viable for several years afterwards, so Bennett worked as a freelance for the Daily Mirror and Mail on Sunday to support himself.[1]
The Chortle Awards were launched in 2002 and in 2014 Chortle launched a comedy literary festival with talks by Monty Python's Terry Jones, and comedy actor Rebecca Front.[2]
Although initially operated by Bennett alone, the site grew into "a proper online publication" with a team of writers including Jay Richardson, Julia Chamberlain and Paul Fleckney, as well as guest contributions from individual comedians.