Hiccup Horrendous Haddock II is the Great Grand Uncle of Hiccup and Snotlout. Hiccup the Second had an interest in dragons much like Hiccup the Third. Hiccup the Second had two brothers, Thugheart and Chucklehead.
Hiccup the Second was abandoned by Grimbeard on a mountainside for being a runt, after which his mother Chinhilda set out on a years long quest to find him, eventually disappearing in the Bay of the Broken Heart. He was found by Grimler dragons and brought up as one with his adopted brother Furious, a Seadragonus Giganticus Maximus. After he was reunited with Grimbeard he quickly became his favorite son, despite their tremendous differences. Hiccup organized a peaceful dragon protest to show Grimbeard the truth about dragons, but Thugheart tricked Grimbeard into believing that the dragons had violent, rebellious intentions. Grimbeard instantly smote Hiccup at the dragon's arrival, leaving a bloodstain on the Throne of the Wilderwest that remains even by the time of Hiccup the Third. Though he quickly realized he had been tricked, the damage was done: an extremely bloody battle had taken place and his son was dead. Realizing the truth of Hiccup the Second's intentions caused Grimbeard to be overwhelmed by grief, banishing Thugheart and dissolving the Kingdom of the Wilderwest. Furious buried Hiccup in the Bay of the Broken Heart, where he stayed to mourn till he was caught and imprisoned on Berserk. The events surrounding Hiccup Horrendous Haddock II's death directly led to the events of the novels.
Hiccup the Second's death sparked the end of the a Kingdom of the Wilderwest, and caused his father to hide the King's Lost Things throughout the Barbaric Archipelago so that one day, a man worthy of the title could become the new King of the Wilderwest.
Inside the Meathead Public Library, Hiccup finds a book entitled 'A Hero's Guide to Deadly Dragons', written by Hiccup Horrendous Haddock II. This goes against Stoick's earlier saying, "Horrendous Haddocks don't write books."
While trapped inside a tree prison on Berserk the life of Hiccup Horrendous Haddock II is told by the witch, Alvin's mother to Hiccup the Third.
- Hiccup the Second was the only Hiccup to not have been King of the Wilderwest.