Iggwilv
Iggwilv, also known as Natasha or simply Tasha, is a malevolent archmage originating from the Greyhawk setting, first mooted in 1975 in the Tsojconth tourney in WinterCon V Detroit (Rock City). She belongs to that small, elite club who represent characters originally played by Gygax and his buddies during the founding of Dungeons & Dragons, such as Murlynd, Zagyg and Mordenkainen. She was male in 1975; retconned female in 1982 because that let her spawn children like "Tsojconth"'s vampiress, and to get funky with demons. (Not that Graz'zt had much of a preference himself.)
Iggy's in-game lore is that she adventured with the OGs, learning much about magic in the process, but ultimately revealed herself as evil and betrayed them, going on to become one of the Great Wheel's foremost experts on black magic and demonology. So much so that Dragon Magazine titled its articles on various demons and Demon Princes as "The Demonomicon of Iggwilv", after a literal book she wrote on the subject. She later got a sourcebook named after her in 5E. She is one of the most powerful people in the multiverse, strong enough that she can beat Mordenkainen in a straight fight, and she also kicks his ass at chess, as shown in the gallery below.
It was rumored that she may be a daughter of Baba Yaga. This was later confirmed, but it was revealed she was adopted instead of being biologically related.
About a century before the Guide to the World of Greyhawk 576 CY, so 480ish, Iggwilv conquered Perrenland and looted the place for her demonological research - for instance, imprisoning the Demon Prince Graz'zt, for her personal manservant and boytoy. A decade later Graz'zt got free, and in the process of banishing him back home, Iggwilv's coterie betrayed her and looted "her" (mostly Perren) wealth. Perrenland freed itself immediately afterward. It was later ruled that she, definitively XX now, survived.
(Literal) Legacy[edit]
A daughter, who guards her vault under The Lost Caverns of Tsojcanth in eternity as a vampire, is (or was) Drelnza. This one was born human. We're not told if she was born before the Perrenland adventure and Graz'zt sexytimes, or afterwards; but since the "vampiress" is in the "Tsojconth" original, before is more likely.
From The Ashes further established Iggwilv for the maternity of the cambion Iuz, who'd later ascend to an actual god on their homeworld of Greyhawk. She whelped him when she kept Graz'zt bound. He later repaid the favour by keeping her as his slave. During this time, Graz'zt decided to have Iggwilv RP Shubniggorath and the two were non-stop boning to the point where Iggwilv carried dozens of his children. These pregnancies were what the wretched hive TvTropes called Express Delivery. She and Graz'zt are currently in mutual tsundere with one another, genuinely loving each other to the extent that either being is capable of love but also too selfish and depraved to express it in any way a sane mind would call healthy. Iggwilv believes that the only demon worth her gaze and attention is Graz'zt, and for Graz'zt, Iggwilv is the only consort he's ever had that he felt longing and attachment toward to the point of jealousy. Tellingly, Graz'zt made it a deliberate point to secret away and protect the identities of all the children he and Iggwilv had through their non-stop bone-sessions.
5th Edition[edit]
Spoilers for a recent adventure
Apparently, all the enemies she made were too much of a hassle, so she decided to lay low in the Feywild in style. She sacrificed a few fey to create her personal domain of Delight and rule it as a persona no one expected: Zybilna the Fairy Godmother of Prismeer. In the time-warped Feywild, Iggwilv turned from mortal into an Archfey. For privacy, while still furthering her ends, the domain of Prismeer was cut off from the rest of the Feywild, using a carnival as a front for the portal. Despite trying to be benevolent as an Archfey, she still has that evil streak, as in Van Richten's Guide to Ravenloft sending "the Caller" after Isolde's compatriots and then manipulating her so she could make her master of the fey carnival that served as a gateway. When Isolde eventually swapped ownership of the carnival with the pair of shadar-kai Mr. Witch and Mr. Light, Zybilna made her forget and sent malevolent fey to hound The Carnival.
During The Wild Beyond the Witchlight, a coven of hags freeze Zybilna and her castle in time, with the campaign's goal being to free her at the request of Iggwilv's warlocks. The book is filled with examples of how to hint to the players Zybilna is Iggwilv, who is Tasha, who is Natasha, which is required to know if you want a wish granted. You can also rat this info off to Graz'zt. In her castle vault are also three jars that depict a person's past, present, and future, with Iggwilv becoming a hag in the future.