Osceola has hosted such artists as Lindsey Stirling, Ben Folds, Echosmith, Kiiara, Velvet Revolver, Big Daddy Kane, J. Cole, Tech N9ne, Lynyrd Skynyrd, American Aquarium, Russell Allen, Red Storm Games, Epic Games, Clay Aiken, Ruben Studdard, 9th Wonder, Pentatonix, Peter Cottontale, Marcus Anderson, Blues Traveler, Obie Trice, Gnarls Barkley, Jason Michael Carroll, Cash Money, Hootie and The Blowfish, PKM , The Contenders, Cravin’ Melon, Corrosion Of Conformity, Confessor, Flat Duo Jets, The Accelerators, Donna The Buffalo, Clay Walker, Roomful of Blues, Erykah Badu, Troop 41, Michael Gillespie, Bas, Yo Gotti, Marc Law, 

and many, many more...