What really connects me to Weekdn's music is obviously my age, (his and Drake are the two biggest artists of our generation) I turn 39 late this month, so Weeknd has been around since I was 25. but the other part is that he evolved a lot as an artist, with a lot of confidence.
He's tried new things, he's gone out of his lane. He shifted into a different kind of artist, lyrics are sharp, relatable, sexual, but not the same way they were 12 years ago. He has developed a style that ages well. and as a persona, he's very background, keeps the focus on his music. it's pop music, but it feels very personal.
His music doesn't feel stuck or trapped in a mindset or age. it feels like it moves as we do.