Born and raised in Flagstaff, Arizona, Gillett earned dual BFAs in film production and studio art, photography, from the University of Arizona in 2004.
Gillett began his film career in the camera department on the Will Ferrell film Semi-Pro. After working as a camera loader, operator and then DP, he began directing short films with comedians from The Groundlings and Upright Citizens Brigade Theatre, and later directed, produced and edited the series Domesticating, Funny in Love and Books, for Fremantle Media.
In 2009, Gillett began working with Matt Bettinelli-Olpin and Chad Villella as part of the collective Chad, Matt & Rob. Gillett co-directed, co-produced, co-wrote, co-edited and worked as cinematographer on three interactive adventure shorts – The Birthday Party, The Teleporter and The Treasure Hunt – as well as the found footage horror short Mountain Devil Prank Fails Horribly. The group became known for their signature style, which blended adventure, comedy, sci-fi and horror, and received nearly 100,000,000 views online.

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