These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
First and Foremost: Because Buddy's originals are associated with the innocence of the '50s, this is strongly enforced.
Germans Love David Hasselhoff: He was particularly popular in Britain, partly because he toured there when other contemporary American stars like Elvis never did. Notably the British press always had the Crickets pose with cricket bats for photos, even though their name was a reference to the insect rather than the sport.
Harsher in Hindsight: When Waylon Jennings gave up his seat on the flight, Buddy jokingly told him, "I hope your bus freezes over!" (the heating on the bus was broken). Jennings replied, "I hope your plane crashes!" Naturally, this haunted him for a long time.
Memetic Mutation: Buddy's glasses. He needed them, but Elton John didn't. He started wearing them as a tribute to Buddy. John Lennon also to some extent.
Replacement Scrappy: The Fireballs, Norman Petty's early '60s house band, who were used to overdub the demo tapes Holly left behind.
Tear Jerker: His wife was pregnant when he died, and she ended up miscarrying.