Skot Olsen spent most of his formative years enjoying the extreme seasonal weather of New England. It was his childhood explorations of cemeteries, colonial homes, and the islands surrounding the coast. This led to a lifelong interest in folklore, dark histories, and the monsters that may be hiding beneath the ocean's surface or in the alley at the end of your street.

Much of his early painting is inspired by the maritime culture of New England, and his body of work surrounding the fictional squid fishing industry of the mid 19th century earned Skot an international fanbase, and helped solidify his reputation in the Lowbrow and Pop Surrealist art movements. He has since been featured in art galleries internationally, as well as producing commercial work for books, magazines, board games, and beer labels. After moving to Oregon in 2012, much of his work focused on the mysteries of the Pacific Northwest, where he spent his time hiking, exploring caves, and searching for buried treasure.

In 2024, Skot produced a body of work for Brassworks Gallery in Portland entitled High Strangness. These paintings and drawings focused on how UFOs and alien life forms relate to religion and folklore. He currently lives with his wife, Karla, in northern Spain where they explore medieval cities, ancient ruins, and a mysterious rocky coastline.