The grit and lyricism that shaped rap in the ’80s and ’90s sounds as exciting now as it did then—arguably even more so when you consider how crossover-friendly rap has become. Here’s a playlist of tracks that capture rap at a moment when it had evolved past the simplicity of its early to-the-beat-y’all days but still retained a rawness that made it feel revolutionary—classics of the golden era. Our editors update picks here now and then, so if you hear something you like, add it to your library.