Dougherty made his feature length directorial debut with the cult horror anthology film "Trick 'r Treat". The film was based on his own script, and was produced by Singer. It played at several film festivals, before being released on DVD on October 6, 2009 in the US and Canada. It received acclaim and went on to gain a cult following in subsequent years. The short film "Season's Greetings", which was the precursor to "Trick 'r Treat", was released as a DVD extra and was aired on FEARnet in October 2013 as part of a 24-hour "Trick 'r Treat" marathon on Halloween.