Once again, the confusion between 'entertainer' and 'artist' comes up here.

Who should get the most respect? I would hazard a guess that the 'entertainers' here probably elevate their own kind more than the 'musicians', the artists, creative trendsetters, pathfinders of the musical world.

Cliffy is a follower. Sinatra was a leader. Plain and simple.

Now, don't get me wrong. I think 'Summer Holiday' was one of the first films I went to see at a cinema (I was 6) and I always liked his hits, even into the 80's. The Shadows almost defined a 'sound' for a generation (although they leaned pretty hard on American surf guitar). In fact, I'd say influentially, the Shadows had more of an impact on music than Cliffy ever did.

Sometimes, you have to step back from what you liked as a kid, and try to put it into some kind of true perspective. The Beatles survive this kind of scrutiny. I'm sorry, but IMHO, Cliffy doesn't. He was part of the soundtrack of my childhood, and I'll never forget his catchy hits. But that's where it stops. He never influenced pop music, and never will. I like the reference to Matt Munroe. That's where Cliffy belongs... The 'almost made it' tribe. Just big enough to be remembered, not big enough to shape the future of pop.
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An arranger is just a tool. What matters is what you build with it..!