Cool has changed from a cultural perspective, but lets not overlook how cool changes from a personal perspective. As priorities shift and people mature, their ideas of what is cool and what isn’t change as well.
Lemme take a moment to make clear that I don’t think being in a band is bad in and of itself, it’s that whole “waiting for the band to take off” mentality that a lot of musicians have. Not everyone has that; you can make music just for fun and understand it’s just a hobby. If you’re in a band but also have a regular career going, I find most people still think it’s cool, or at least interesting.
That said, being a musician in late high school \ early college will probably be much more of a panty dropper than being a musician in your late 20s. When you get to your late 20s, the biggest panty dropper you can have is your shit together.
That’s because as you grow up, your C position changes not only in a geographic sense, but also in a world-view sense, where you become more and more aware of the important things in life as time progresses. Practicality comes into the equation, and it plays a bigger role than you might think. When’s the last time you met a cool person who couldn’t sustain themselves on their own income?