Billy on the Street (2011)

Comedian Billy Eichner, unfiltered and unapologetic, hits the streets of New York City to test unsuspecting strangers on their knowledge of music and pop culture. With microphone in hand and money in tow, Eichner gives contestants the chance to win cash by answering a series of hilarious and spontaneous questions. The catch? The final round is subjective - Don't agree with Billy? You lose.