The Dickest Share definition Flag To call something "The Dickest" means that it is the flyest, illest, dopest, hottest thing you have ever seen, heard, felt or known. "He's THE DICKEST rapper in the game." Or: "That vintage blue mustang is The Dickest, yo! " The Dickest by biancasunshine February 8, 2009 Get the The Dickest mug.