49. Cardi B, Invasion of Privacy
Cardi B was not even born when MTV was pumping Max Headroom as the avatar most representative of a generation. However, in 2018, she conjured up the character for her album Invasion of Privacy. Outfitted in a white and black checkered suit, the Bronx beauty is portrayed as a caricature, aptly capturing the spirit of the project. Her bright yellow kitten wig is only but one element of animation that stands out. Another of course is her crooked smile, as if to say the joke is on all of you. The 80s inspired cover was retro and futuristic at the same time, encouraging us to believe that Cardi also has that level of generational stay-power.