Born in 1984 in Boston, MA, Hollingsworth grew up in Florida and has lived in Minnesota since 2000. He currently resides in Saint Paul, Minn. In 2012 he was a fellow at the Virginia Center for the Creative Arts in Amherst, Va, the Ragdale Foundation in Lake Forest, IL, and he completed an artist residency at the Lanesboro Art Center, Lanesboro, Minn. In 2010 and 2011 he completed residencies at Tofte Lake Center, Tofte, Minn under the auspices of the Jerome Foundation Emerging Artist program. In 2011 he was awarded a Minnesota State Arts Board Artist Grant. His work has been shown at Nina Bliese Gallery, Minneapolis and at Locanda Toscanini, in Tuscany, Italy.