1. (adj)devilish, rascally, roguish playful in an appealingly bold way
"a roguish grin"
2. (adj)rascally, roguish, scoundrelly, blackguardly lacking principles or scruples
"the rascally rabble"; "the tyranny of a scoundrelly aristocracy" - W.M. Thackaray; "the captain was set adrift by his roguish crew"