I’m of the opinion that you really want an artist that’s either really far along in their musical career, towards the end of their musical career, or they are deceased and their musical career is over to make a music pin.
I really like music pins and nearly all of the best music pins are not even “my generations” music. These are bands or musicians that have been around for many decades and bridge multiple generations.
When you get a true musician that have been or were around for decades they have a big catalog of songs, artwork, performances, albums and album covers to draw from for inspiration. It’s essential timeless. If you pick a new artists, they may not even be at the peak of their career. They could be at the beginning, middle, or even nearing the end. If you made a pin with their current catalog of music and they went on for another 20 years I don’t really see how that will hold up long term and it would get really dated (regardless of how good the musician is). It would be like if you made a Madonna pin right after Like a Virgin came out. There’s so much material that came out afterwards, that it would just trap it in a certain era and keep it dated.
Getting your own pinball machine isn’t something that artist just get for writing some chart topping songs and being huge for a while. Bands like Metallica, The Beatles, The Rolling Stones, AC/AD, Guns N Roses etc. are massive, have been around for decades and transcend generations.
Look up how many gold records Elvis has for that matter.
Anybody that calls this stuff “dad music” or “old man” music or whatever they think the funny pigeon hole term they want to use really is not a fan of music in general in my opinion. Music isn’t about age groups. Anybody that categorizes it as such knows Jack shit about what real music is. More than half of what I listen to are musicians from before “my time”. I listen to plenary that came out while I was growing up and a young adult, and yes I listen to current “new music” as well. There’s not a single “new artist” I think “deserves” a pin.
This is something that occurs when you’re a music icon.