Now matter how I flip I'm a flip hiphop Greg Nice – Set It Off (Back to the Old School)
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Union Square is located at the intersection of 14th St, Broadway, 4th Avenune, University Place and Park Avenue South in Manhattan. Historically it has been the location of many protests and demonstrations, as far back as the 1860s and as recently as the 2000s.
In the 1990s, at the time of the writing of this song, there was a lot of construction in the area and Union Square was frequented by a diverse mix of long time east village residents, artists, students, drug dealers, prostitutes, homeless people, and New Yorkers from every other walk of life that spent their time downtown.
The context of the previous line (“let’s take it back to the old school”) implies that here Greg Nice is referring to Union Square in the ‘80s, when it was a spot for hip-hop heads to gather and rhyme.
I’m pretty sure Greg is referring to the actual Union Square nightclub, a famous 1980’s hiphop club in NYC, and not cyphers in the park. This would make more sense, given the context of the next line, talking about the Latin Quarter.
See this link for more background on NYC hiphop clubs at that time: