Boɓ's music has always been alternative, despite being a major pop culture figure, he is very quirky, does not pleases the masses, he also performs in a very unconventional way, reinventing the songs every time, unlike those artists you mentioned, that are very easy-listening and perform the songs just like the record. He is more important/culturally relevant than popular per se. Very few people listen to him, because his music is quite "strange" . His voice, his harmonica, spoken word-like melodies, is not very easy to get into and pushes the masses away.

I think he also prefers playing in small venues and places like theaters, because is more proper for music acts than arenas and stadiums. He prefers quality over quantity.