Highshot Share definition Flag A cross between a highroller and a hot shot who has mad cash and a hot woman Yo brotha, Look at that guy comin in the club with the smokin hot blonde on his arm flashin his money around. Anyone that rolls like that wit a woman like her gots to be highshot! Highshot by DIRTY$$$$ March 21, 2013 0 0 Get merch Get the Highshot mug. Buy Now — $32.95 See more merch