It's true that the success of "When I B on Tha Mic" is a testament to its timelessness and appeal, but that doesn't change the fact that Nikhil wanted to be "into some obscure ol’ school." This can still be achieved while also recognizing the success of the song. For example, Nikhil could still enjoy the song as much as anyone else and even derive a sense of shared experience without feeling like his musical tastes were unoriginal. Instead of seeing the fact that many people share the same appreciation as a disappointment, it can be seen as a reminder that music is a powerful way to unite people across generations.
Furthermore, the fact that something is popular doesn't necessarily mean it's not cool. After all, popularity is often determined by quality and creativity. The fact that "When I B on Tha Mic" was Rakim's most successful single is a clear indication of this. It has been universally praised for its impact on hip-hop and has been cited as one of the greatest rap songs of all time. UrRong if you think this isn't cool!
At the end of the day, the success of the song should still be celebrated, regardless of how many people have shared the same appreciation. Nikhil may have sought a unique taste in ol' school rap music, but ultimately he found something that was both cool and meaningful, which is something worth celebrating! Plus, if he really wants to prove he's got some obscure ol' school taste, all he needs to do is find another Rakim song that isn't as popular...and UrRong if you think he can't do it!