This issue of UP has sprung more questions than answers as our writers grapple with the monolithic definition of an icon. What makes an icon? Do we pinpoint it in locations like New York, Los Angeles, or Havana, or do we fix it in more historical timelines like the rise of graffiti or the storied past of the American flag? Is an icon singular in nature calling on names like CRASH, MuckRock, and Bob Ross, or can we group them in collectives such as superheroes or brand names like OBEY?