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So the next question is "is it worth finding?". Bing Crosby probably isn't worth finding. He had a nice voice, but that's it. He wasn't creative. He was just another singer. Same with Sinatra.
I think that's more than a little unfair to Bing. He was instrumental in pushing for advances on the technical side as well, being one of the major forces pushing the industry into using magnetic tape and the entire practice of pre-recording performances. He pioneered his style of singing to take advantage of the technical development of the microphone, and his singing style (incorporating different phrasing techniques and practices from jazz) was revolutionary. He was enormously creative in his music - but much like Orson Wells, so much of what he created is now just "normal." it's just "singing" - it doesn't seem like anything creative. Also he was an Oscar-winning actor and one of the more successful box office draws of his time, FWIW.
But...I hear you. Writers and composers are going to have a longer "lifespan" of cultural relevance than performers, because what makes their work special can still exist in new forms long after they've passed. New performances by a performer can only come about during their lifetime, but new performances of a composed work by new performers can happen on an ongoing basis. Sure, students of music might dig out Perlman's performances of Mozart - but Mozart's cultural importance will be vaster than Perlman's, because Mozart's works will be being performed anew, while Perlman's are frozen in time.
I do think that musically we are experiencing an era of sameness. Lady Gaga, Taylor Swift, Ed Sheeran, and more, are very talented. Good writers, good singers. Lots of fans, of course. But it seems to me that they lack that *something* that will endure for 100 years or more.
Hard to say. Cultural penetration is important to lasting endurance, also. Returning to the thread topic, it's not at all surprising that an "ordinary" mid-20's person doesn't know who Carlos Santana or Eric Clapton are. Neither of them were "mega-superstars" even at their peak. Certainly not Santana. Probably not Clapton, either. Yes, he was an enormously successful artist, but didn't land as hard broadly as the mega-super-duperstars of the eras (Zeppelin, the Eagles, Fleetwood Mac, and still the Stones on the rock side, Bee Gees and Abba on the pop/disco side, Elton John and Queen somewhere less categorizable). You can certainly argue that Clapton had skills and talent that some or all of the performers in those groups lacked - he's probably one of the greatest electric guitar players of all time. But they had a level of stardom that leads to lasting impact and endurance that Clapton never hit. Not for lack of talent, but because what he wanted to do musically wasn't necessarily going to get him that type of commercial megastardom.
If Taylor Swift is going to still be culturally relevant in fifty years, I suspect that it will be because of that megastardom. The "Abba model," if you will. If you're one of the most popular performers on the planet for long enough to build up a massive discography of hits that people will still be humming well into their golden years, you can achieve that kind of legacy.
