Babies and toddlers may look all cute and cuddly when they smile and coo at you. But, not all kiddos are born with innocent halos on their heads.

In fact, some of the tiny tykes who crawl out of the womb are nothing more than punks, thugs, and world-dominating gangstas! The only rules they play by are mob boss rules, and even then they might surprise you with their cheeky lawlessness.

From the irreverent tot cop who constantly blocks in the neighbor’s car with his mini cooper, to the high flying ladies man who’s got lots of swagger, here are 75 of the most badass boss babies ever known to man.