Just the random musings of andymooseman.
When you mentioned Matt Monro, I immediately thought of "Racing with the Moon" which proved to be Vaughn Monroe's (the American baritone) signature song. But, yes, I certainly remember Matt with hits like "Born Free", "Softly as I Leave You", and "Walk Away," all of which had a plaintive quality. I can understand Sinatra's admiration for Monro. More than a passing similarity in the quality of their voices—a bit of self-love going on there on Frank's part?
I'll be honest & say that i don't really know Matt Monro's music very well at all. It was only when i helped arrange that gig & met his son, that i found out all about him. An interesting character & with a very fine voice, by all accounts.Nothing like a bit of self love :)