Does a particular musician’s songwriting and artistry speak to you above all others?

Richard Thompson, his life's work of songwriting is simply incredible and far ranging. Frank Zappa and Robert Fripp.

Not really.
Perhaps the best metric is goosebumps and/or tears.
An involuntary human reaction that is actually measurable and even manifests in a physical response.
Hard to beat as a “metric,” I’d say.
If I had to guess, I’d say Stevie Wonder has probably caused me to experience those more than anyone else.
Nevertheless, I would feel weird saying I “hold him above all others” or something like that.
Waaaaaaaaaay too many artists for that.

I seem to be entirely incapable of getting sick of Norm Macdonald, no matter how hard I try.
Maybe comedy is an art form where I have my own personal “Chris Standring.”

When Michael Hedges got going he was indeed mesmerizing.

Another outstanding musician who left the planet way too soon.

At their best it's Miles Davis and John McLaughlin.

Jerry Garcia / Robert Hunter

Lyrics, guitar and voice melt into a dream.