He’s always straddled the line between loner and consummate hipster…
His greatness, from a Canadian perspective (in Canada's The Walrus):
The romance that Neil holds for American listeners is obvious; he’s
always straddled the line between loner and consummate hipster. His
charm seems accidental, as nothing about him seems to make sense: his
lyrics consist of one-liners pieced together with nonsense, and they
rarely seem as punchy on second thought as they do when he delivers
them; his guitar technique is like that of a kid trying to emulate his
heroes before he’s finished learning how to play. At his most
interesting, Neil is a relative moderate embroiled in a world of
excess, chronicling his friends’ downward spirals with insight but far
from square himself. In short, he’s always been cool, but he’s never
been a fuck-up or a ham.
Some people call this mystique; I call it Canadianness. The
qualities that make Neil so appealing to young Americans are the ties
that bind him to his place of birth. And these qualities look much
better from a distance—shyness and reserve go nicely with a Laurel
Canyon pedigree. He has the bearing of someone who grew up in a tougher
climate, who had some experience with manual labour but plenty of time
to think. It’s worth noting that 2005’s Prairie Wind, on
which he sings of Canadian geese and the Trans-Canada Highway, was
recorded in Nashville: The North has its own cachet, comparable to that
of the South. Neil has a certain northern authenticity, from his
discovery of “Four Strong Winds” on a jukebox in the prairies through
his early days playing folk clubs in Winnipeg and Toronto. If you grew
up in New York City, Neil’s early life might seem awfully interesting.
If you grew up here, there’s a good chance that his adolescence was
similar to your dad’s.
The problem with this analysis is that it makes the mistake most rock writers made, which is to assume that everything is about attitude. (For instance, the line about Young not having learned to play guitar, which is kind of like saying Count Basie didn't know how to play piano, because he didn't play a lot of notes. It's absurd.)
But with that said, it's true that Young is about as reticent as rock stars get, and probably yes, that has something to do with being a Canadian.