Hiccup Horrendous Haddock III faced numerous challenges on his journey to become the last King of the Wilderwest. One of the key challenges was his encounter with a witch who believed Alvin was the rightful heir to the throne. Hiccup had to use his wit and cunning to escape from her clutches, even discovering a key in the most unlikely of places - his dragon Toothless' stomach! He also had to deal with the legacy of his ancestors, particularly Hiccup Horrendous Haddock I and II, who had their own complex histories with the Kingdom of the Wilderwest. Despite these obstacles, Hiccup's determination and bravery saw him through, proving that he was indeed the rightful King of the Wilderwest.