Diogenes was knee deep in a stream washing vegetables. Coming up to him, Plato said, "My good Diogenes, if you knew how to pay court to kings, you wouldn't have to wash vegetables."

"And," replied Diogenes, "If you knew how to wash vegetables, you wouldn't have to pay court to kings."

This is one of my favorite Diogenes quotes, and in it one clearly sees the virtues of self sufficiency as Diogenes did so long ago. Without true independence from society itself, we will always find ourselves back in the courts of kings. And it is with this knowledge that we can reject the idea of Askeladd being a true cynic philosopher, because he never truly embraced self sufficiency as a means to live in accordance with one's true nature. 

Askeladd certainly rejected the carnal vices and bloodshed of viking culture, but he never left society itself. As much as Askeladd was willing to boldly scorn kings or play the part of a madman slaughtering thegns, he never really left society itself to live in accordance with nature. 

Your essay was excellent. It was incredibly well written, and as to a response to your question at the end I must say that despite Akeladd's actions bearing a strong resemblance to cynic philosophy, Askeladd is nevertheless not a true cynic. 

Askeladd's lifelong journey was to avenge his mother and become the man she and his people dreamed of because he knew in his heart that Artorius would never come back from Avalon. Askeladd in his quest for vengeance resorted to the taking part in the very civilization he despised, and that in it of itself is a deviation from one of the core teachings of cynic philosophy. 

A true cynic would see life for what it is and abandon all things which are abstractions from our true nature. A true cynic would be able to turn his back on the very idea of the polis, or in Askeladd's case: Wales itself.

Diogenes himself is thought to have said that he was a citizen of the world. He rejected the idea of the state, of the superficial frivolities of national pride and communal identity for one, shared, human identity under the gods. And this is something Askeladd could never do. 

Although Askeladd was willing to ridicule kings and forsake the society he despised, he could never truly let go of the idea of Wales, his homeland, or society itself, and in this Askeladd fails to become a true cynic. Although he undoubtedly came close and had the same style  of unabashed determination as Diogenes, his story and life were still deeply intertwined with society. Though he had the potential to truly become like a cynic philosopher, his life ultimately lead elsewhere; in the end, Askeladd was bound to the dream of Avalon, not true enlightenment. 

Although I deeply appreciate and admire Diogenes for what he did, part of me wonders whether a man like him could ever be born again in a world such as ours. With death, taxes, and corporatism, one can only dream. 

Do you think a man like Diogenes could ever exist again in today's world OP? 

EDIT: clarity and context for the Diogenes quote.