Pos rep just for the fact that the old forum doesn't have these kind of topics anymore.
Listening was an anchor in my life as a Senior in Durham when it dropped, and being around the whole NC hip-hop scene at the time. That album is timeless. Real coming of age album for me too. They broke new ground on there, and it's just a perfect album.
That said, The Minstrel Show I think is better lyrically, flow-wise, and production wise. The skits and concepts/humor flow just as well, and objectively, I feel like it is a better album. I also have a strong attachment to that album as well, and it gets more spins from me now than Listening does.
Both 5 mics to me.