The name Dapper Dan is one that requires no introduction. The fashion icon, whose artistry completely shifted hip-hop culture in the 1908s and early ‘90s, is finally getting his flowers all these decades later. Most recently, it’s from the Council of Fashion Designers of America (CFDA), where the designer will be awarded at the annual Fashion Awards with the Lifetime Achievement Award. The history-making honor marks the first time that a designer with no prior fashion shows will be a recipient, and it’s something that the legend doesn’t take lightly. ESSENCE sat down with Dapper Dan to hear more about his reaction to the news, took a deep dive into his unconventional journey and even challenged him to a quick game of Guess Who?