Henchy was a Writer and Producer for television sitcoms Spin City and Life With Bonnie. He created the sitcom I'm with Her with Marco Pennette, which was loosely based on Henchy's relationship with wife Brooke Shields. The show was cancelled by ABC after one season. Henchy later became the co-executive Producer of Entourage and a Producer on HBO's Eastbound & Down. He, along with Will Ferrell and Adam McKay, created the website Funny or Die. Henchy produced The Goods: Live Hard, Sell Hard. He is credited as a Writer of the 2009 film Land of the Lost, The Other Guys and The Campaign which he also co-produced. In March 2018 it was announced that Henchy will direct a feature-length movie for the Impractical Jokers television series. The film will be produced by Funny or Die. The film is set to go into production in Spring 2018.