Like Manhattan in the 80s and 90s?

UPTOWN

Think of the direction you’d head to reach Harlem from Midtown in that era.

This clue plays on the phrase "uptown," which was slang for stylish or sophisticated in the 80s and 90s—especially in hip-hop and urban culture. Manhattan’s uptown neighborhoods like Harlem were cultural hubs during that era, so "uptown" became shorthand for something cool or elevated. The answer isn’t about location but the vibe of the time, making it a clever nod to pop culture.