Originality is a tough one, because everybody's got an influences (the more well-rounded you are the more original I guess). Creativity, I meant per song. Lots of artisits are technical, per se, but every song entails the same format, style, and solo chops. Technicality and showmanship speak for themselves. But...
Is classical really more technical than blues? It's more precise. Is one who spends just as much time practicing the blues as one practicing classical less technical? I've never heard a better blues player than Hendrix, who spent his entire life learning it .. are you going to tell me that somebody who spent his/her entire life learning classical is more technical? Is classical harder to play than blues? Many would say yes, but lets see one of you solo improvise a blues solo at the same level as Hendrix. (Listen or watch Hendrix's last concert, Isle of Wright, playing red house, and tell me if you could pull off an improvised solo at that level. "yeah but it's basic pentatonic stuff.." Don't even get me started on that **** - for reasons posted above.) They're both 'hard' it's just that the two concentrate on different things: precision and accuracy, and chops (solo repitoire) and creativity.
They're two different styles, but mastering one is as hard as mastering the other. Same with jazz, country, folk etc.
So, in the technicality category, he/she who is the most progressed player in any one category is the most technical of them all. It's all for nought if their work isn't original or creative, or they can't reproduce it live.
Since it'd be impossible to have somebody knowledgable in all styles enough to judge one technical player against another, what it comes down to is the simple calculation of the amount of time each one has spent perfecting his/her art. One player is more technical than another if he or she has spent more time perfecting the art. Hours logged.
"But a fighter pilot with 10000 hours logged just got shot down by one with 2000 hours logged." Natural talent?
You sure as hell can't go by records sold or airplay. You can't go by style or how technical one is unless you count the amount of hours each one has, and even that is an unreasonable way to go about it.
Conclusion: Personal opinion... OH WAIT, you could judge by how many people ones playing has affected, the most influencial in both musicians and audience. and THAT may or may not even have anything to do with technicality. How would you judge that though, survey? And this thread is a survey right here and the winner is so far...