The Wanderings of Wuntvor

A trilogy of comedic satire Heroic Fantasy novels, individually called the Ballad of Wuntvor, written by Craig Shaw Gardner. Sequel to The Exploits of Ebenezum.

After saving Vushta from the Netherhells and defeating Guxx Unfufadoo, Wuntvor believed that his master would at last be cured and he could finally begin to learn magic at his side. Instead, Ebenezum's curse spread to infect the entire Greater Vushta Academy of Magic and Sorcery! So, Wuntvor is set out on a dangerous quest to the Eastern Kingdoms of Mother Duck. It will not be easy, as even more trials and tribulations stand before him... not least of which his many allies seeming to fall apart, leaving him to continue on alone.

In addition to tropes from The Exploits of Ebenezum, this series contains examples of:

 * The Chew Toy: Wuntvor again. In fact, Death reveals that Wuntvor is but the latest incarnation of the Eternal Apprentice, the least and most offensive (in Death's view) of all the "Eternal Hero" archetypes. Wuntvor will basically never be able to become anything more then an apprentice and will forever be roped into the sort of weirdness his career has given him so far. And then, when he dies, he'll instantly be reincarnated to experience the same sort of mess again. And again. And again. For all eternity.
 * Token Evil Teammate: At first glance, the Dealer in Death. Then Guxx and Brax join the group...
 * Too Dumb to Live: Slag, Grott and Vermin, the so-called "Apprentices Guild" of Vushta, who try to bully Wuntvor into either curing their wizard masters or handing over ridiculous amounts of cash. They cement themselves as this when the very first thing they do after Wuntvor persuades his built-like-a-tank assassin "friend" the Dealer in Death that he does not need to wring their necks like chickens for a pot, as surely they will be reasonable, is to repeat their demands for a cure or 200 gold pieces by moonrise tomorrow. Not even the slightest bit phased by what just happened, or the fact the Dealer still has his hands around their necks. And then they repeat it a second time while the Dealer is still standing just behind them -- though they do at least take off immediately after saying it. No matter how often they end up being chased off, they continue to pursue Wuntvor and demand ever-increasing amounts of money.