Larabie was born in Ottawa, Ontario, Canada. In his self-published autobiography, he states that he spent much of his childhood in the cottage country of the Ottawa Valley, an isolated environment that did not allow him to have traditional friendships or social activities, and thus spent much of his time learning computers and typography; he graduated from Sheridan College with a degree in classical animation, a field that was largely obsolete by the time he received his degree. Larabie was employed at Rockstar Canada and had contributed his designs to multiple video game titles, including the hit series' Grand Theft Auto and Max Payne, before he quit the company in 2002 to focus full-time on type design, after having released a series of freeware fonts over the Internet under the brand LarabieFonts since 1996. Larabie worked as a video-game artist at Rockstar Toronto until 2002. While he did not design fonts for the company directly, his 1999 Pricedown font was later used in the logo of the Grand Theft Auto series. He moved to Nagoya, Japan in 2008, maintaining his Canadian citizenship[3] and returning to the country briefly in 2017 to celebrate its sesquicentennial.

Larabie primarily specializes in novelty typefaces that are intended for use in desktop publishing and graphic design. The logo for Grand Theft Auto, for instance, uses Larabie's Pricedown font, which is based on the logo for the international game show The Price Is Right, as well as for the Disney animated series Fillmore!. In addition to game shows, Larabie has also used 1960s and 1970s graphic logos, computer emulation, and other inspirations to design his fonts; most of his designs are display faces not meant for body text, with Larabie acknowledging that he had difficulties with italic type and, especially in his early career, had difficulties adapting katakana and hiragana to his designs.[3] He is particularly known for his “ubiquitous futuristic and sci-fi fonts”; Larabie specialized in that style early in his career because he felt that, other than a few examples such as Bank Gothic, Microgramma and Eurostile, the market for that style was underserved.

Two of his typeface families, Marion and Superclarendon, are released with macOS. Larabie's "Canada 150" is an extended version of his previous font Mesmerize (in turn based on 1920s calligraphic German sans-serifs such as Semplicità, Nobel and Kabel) with Cyrillic and First Nations alphabets included; it was commissioned by the Government of Canada to be the official typeface for the country's sesquicentennial. The government paid him nothing for the custom work, which he subsequently placed into the public domain. He would proceed to release large portions of his Larabie Fonts library (inasmuch as he could, since some of the designs were derived from freeware that turned out to be copyrighted and thus could not be re-released), along with less successful designs for Typodermic, into the public domain in 2020, 2022 and 2024.