I don't remember the original Dean Martin then. I only remember the famous crooner who played the straight man to a popular comedian in a series of well loved movies.
Bing Crosby and David Bowie's duet of the Little Drummer Boy- a UK Top 10 hit in the late 70s after Bing's death.
Growing up I don't recall having any music playing in our house whatsoever. I cannot say why that was or was not. One memory of a comment on music was after I had been in the service and returned to live with my parents for about six months before I got my own apartment. I had bought my first stereo in Korea and brought it home with me. I had it sent up in my bedroom and I am sure I blasted my parents with my sounds. The only interchange I recall is one afternoon when my mother came upstairs and knocked on my door. She asked what I was playing. I told her is was Arlo Guthrie from the album Hobo's Lullaby and the song Ukulele Lady. My mom then went on to explain as a young girl while living on the family farm she would play the Ukulele as others would dance at family gatherings. She had never mentioned that before but I will remember it forever...
I’m no Zeppelin fanatic (barely listen to them at all for over 25 years — give me solo Robert Plant over Zep any day)… …but for the life of me, I don’t get how Greta Van Fleet is supposedly the new LZ. Admittedly I mostly only know GVF from their one (or was it two?) Saturday Night Live appearances — but the comparison was laughable. And, again, I haven’t listened to more than 3 Zep albums in the last 10+ years — so I’m not saying they’re rock gods or anything (certainly not to me).
Music got quite a bit different after Bing Crosby, no? And I happen to like Bing Crosby, CSNY, Greeta Van Fleet, Led Zeppelin, Michael Buble (most of the time), whoever.
I’ve been recently reading Gary Giddins’ wonderful biography of Bing, and in those early days of Bing’s popularity to succeed as a singer you had to be a “high Crosby or a low Crosby.” Several times over the years across different countries singers were named their country’s Bing, like Michael Holliday being Britain’s Bing.
More importantly I never heard anyone back in the day say "what genre is this?" It was all just a melting pot. I get asked all the time by kids what genre something is and my answer is always the same: "Symphonic punk country disco babymetal."
I have a feeling this probably did happen more than we think in the old days, it’s just harder to dig up the primary sources. Certainly in jazz you had the new Bird, the new Clifford Brown, etc.