cuban steamroller Share definition Flag A cuban steamroller is when a person does a roly poly and shits as he rolls. Wow, did you see that guy do a cuban steamroller last night?Hell yeah, what a weirdo. cuban steamroller by DoleDUck February 24, 2014 0 0 Get merch Get the cuban steamroller mug. Buy Now — $32.95 See more merch