Henchy was born in New York City. After leaving the city, his family spent some time down south, with Henchy spending his early years in Augusta, Georgia, then attending high school in Friendswood, Texas where he worked at a local movie theater and took in every film he could. Despite his early love of cinema, Henchy went on to earn a degree in finance from the University of New Mexico and returned to New York for a job on Wall Street. After a spell as a finance guy, Henchy felt the itch to write jokes and initially struggled to find work before getting hired by MTV. But it wasn't until he found his way into Garry Shandling's circle that he earned his comedy stripes writing jokes for the cult favorite "The Larry Sanders Show" (HBO 1992-98). Henchy then went on to tackle the sitcom genre, writing for the series "Campus Cops" (USA 1996). After writing for a few TV specials and some guest-writing stints on series, Henchy took a stab at creating his own pilot with the short-lived series "Battery Park" (NBC 2000) starring Elizabeth Perkins as a hardboiled NYPD cop. While the show was canned after only four episodes, Henchy took credit as co-creator, writer and supervising producer, proving his early showrunning capabilities. After the show's untimely end, Henchy moved onto greener pastures, taking over as a supervising producer and then co-executive producer on the hit series "Spin City" (ABC 1996-2002) starring Michael J. Fox. After the success of "Spin City," Henchy took on another supervising producer job, working on the series "Life With Bonnie" (ABC 2002-04) featuring Bonnie Hunt. Henchy's next show was based on his real-life experiences. Teaming up with his former "Spin City" colleague Marco Pennette, Henchy created the sitcom "I'm With Her" (ABC 2003-2004) based on his relationship with his wife, Brooke Shields. The series centered on a high-school teacher who becomes romantically involved with movie star after a coincidental meeting. Henchy first became friends with Shields in late 1998, when he was writing for a Christmas in Washington special on NBC that Shields was hosting; the couple married in 2001. "I'm With Her" managed to last one season, but was considered a poor television rendition of the film "Notting Hill" (1999) by critics. Henchy took the setback in stride and returned to his HBO roots, taking over as executive producer on the series "Entourage" in 2005. The following year, Henchy joined Will Ferrell and Adam McKay at Gary Sanchez Productions, a production company connected to Paramount. After kicking around an idea for a comedy-video website, the three partnered with Sequoia Capital to launch Funny Or Die in 2007, which became an online destination for emerging comedians and viral content. As the site continued to find its legs, Henchy tried his hand at writing a screenplay, adapting the popular 1970s sci-fi series "Land of the Lost" (2009), starring his friend and colleague Ferrell. The film was generally panned by the critics, but that didn't dissuade him from trying again, this time writing and producing the spoof cop comedy "The Other Guys" (2010), starring Ferrell opposite Mark Wahlberg, which met with more success. Along with his other cohorts at Gary Sanchez Productions, Henchy produced several comedy series and films and successfully adapted several Funny or Die web series into television shows, including "Funny or Die Presents" (HBO 2010-11) and "Drunk History" (Comedy Central 2013-). During this time, Henchy collaborated with his friend Danny McBride on the comedy series "Eastbound and Down" about former major league baseball player Kenny Powers, who's forced to return to his hometown and become a phys-ed teacher. Henchy produced and wrote the screenplay for "The Campaign" (2012) starring Funny or Die star and comedian Zach Galifianakis, before taking a break from the genre to produce the supernatural action thriller " Hansel & Gretel: Witch Hunters" (2013).