Song choice advice: Obscure vs popular music?

Beginner performer here!

I know it's not the one and only factor to consider in choosing a song to perform to, but I do know that song choice can be really integral in selling your performance and story. I've seen a lot of experienced artists say that it really doesn't matter what kind of song you perform to as long as you can connect with the audience. However, I've also seen just as many, if not more performers say basically "you really kinda have to perform songs/artists that are popular or nobody's gonna respond to it well." citing that they tried performing obscure music and it didn't go well or that some clubs are gonna force you to perform top 40.

I find the music that I listen to and think "wow that would be great for a number" do tend to be a bit on the "obscure" side (like maybe 100k-1m total spotify streams?). Any advice? Should I try to pivot and find more well-known music to perform that still matches my aesthetic or just let the performance do the heavy lifting?