Middleditch was born and raised in Nelson, British Columbia. His parents are British. He was cast in a play in grade eight which he said "changed everything" for him. He went from an indoorsy kid who was bullied, to becoming the funny, popular kid in high school. He discovered improv in grade school from performing with Theatresports.\n', '

He studied at the University of Victoria before moving to Toronto, where he auditioned for and enrolled in George Brown College, but never attended classes. He instead opted to make sketches on his own, and worked at a New Balance store for an income. He then relocated to Chicago, where he took classes at The Second City and iO Theater, while also performing regularly. Due to immigration issues, he worked various cash jobs until Charna Halpern sponsored him to get his work visa. While performing on a Second City cruise, he got an audition for Saturday Night Live. Though he did not get cast, the routine he used in his audition landed him a network holding deal and he moved to New York City.\n', '

While living in New York City, Middleditch began acting in commercials. In 2007 a sketch video for Chicken McNuggets he made with Fernando Sosa in Chicago was purchased by McDonald\'s and used as a commercial. He appeared in the 2009 romantic comedy Splinterheads, portraying the lead role of Justin Frost. On March 25, 2010, he joined a CBS pilot Hitched, written by Josh Schwartz and directed by Rob Greenberg. On May 5, 2011, Middleditch made his first appearance in Jake and Amir, in the episode "Jake and Amir: Doobs". He made several returns to the web series.\n', '

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