Cooldady Share definition Flag A male pimp, dealer, or playa who is unconcerned with the Feds catching up with him and his currupt ways and also with a burning heart, ready to take action. Hello Cooldady. Cooldady by Cooldady December 4, 2019 0 0 Get merch Get the Cooldady mug. Buy Now — $32.95 See more merch