Cindy the Flameskull

Bad to the Bone

Cindy the Flameskull was the dismal result of an experiment gone awry.
Born in 489 AXR, Cindy had an abhorrent upbringing, abandoned at birth and left to the hands of the Children of Shadowed Faith - a necromantic cult nestled deep beneath the catacombs of Ravencrest. The child was named Dregh'enir, after the legendary wizard that killed the Dragon tyrant Kavras millennia ago, and the Elder cultists watched his career with great interest. He learned to worship the dark lords of the Shadowfell, read from the ancient texts cast in darkness and drink from elixirs brewed in liquid evil (standard edgy warlock shenanigans). His affluency with pyromancy quickly gained him the nickname 'Archmage of the Cinders' within the cult.
In a sudden bout of greed, the Children of Shadowed Faith attempted to take the city of Ravencrest for themselves in 527 AXR, convinced that the forces of life and death should reign side by side. The cult, through crafting a phylactery and crushing up samples of Witherthorn Rose into a lichnee potion, attempted to descend into lichdom. Whilst some succeeded, the most powerful becoming liches and others demiliches, Dregh'enir was instead reduced to a flameskull, making him a laughing stock among the order. He was outcast and nicknamed 'Cindy', a snide parody of his former alias 'Archmage of the Cinders' by his peers, forcing him to leave Ravencrest forever.
With his reputation tarnished, he set out on his own to become powerful again but was promptly captured by an adventuring party who revelled in his misfortune, throwing him around like a basketball and hanging him on a tavern door as a 'Do not Disturb' sign. This vicious cycle continued as his parties kept dying and he was passed around from person to person. Eventually, he managed to break free in Ablefell when his party traded him for a scroll of true strike, floating away to the mortuary. However, when he was found by the mausoleum groundskeeper, he was promptly locked in a coffin after being mistaken as a resident.
Months passed by and Cindy was finally freed by another adventuring party, the Masters of the Nine Elements, who, instead of treating him maliciously, welcomed him as an extra member of the party. So, for two months, Cindy the Flameskull finally got to be the hero he wanted to be, before his tragic death at the hands of Dr. Qhasrel in Hemlock Asylum.