While I feel like popularity and quality is orthogonal as it relates to artists, it feels like they are strongly related when talking about songs from a single artist. I suppose there is a familiarity bias and one often likes what they have heard most...radio songs have a way of growing on you, but I feel like if you go through a new artist blind, there's a good chance you'd end up picking the popular songs more often than deep cuts. Like, they aren't choosing singles randomly.
Inspiration of this thought is I've been working through Taylor Swift's catalog and the singles predominate as the ones I'd pull for a greatest hits, even on the first album whose singles aren't really familiar to me.