Funniest pretending-to-be-black was Mindy Kaling's brother https://www.nbcnews.com/news/asian-america/mindy-kalings-brother-i-posed-black-get-med-school-n337026 "...he shaved his head, trimmed his "long Indian eyelashes," and used his middle name, Jojo, in an attempt to pass for black. His application also stressed his time spent in Africa, where he and his family lived before moving to the United States."