Legend Mama is an online character sheet creator that inverts the traditional character creation process, starting with character personality and backstories, to produce unique, playable character sheets. For new players, Roleplay Driven Character Creation (RDCC) simplifies the character creation process and encourages roleplaying. For seasoned players and DMs, it offers the opportunity to explore complex and challenging character builds. The application utilizes GPT, an advanced generative AI by OpenAI, to translate character backstories and personalities into character sheets. To ensure character sheets are playable, the application performs rigorous checks against D&D 5E rules and makes corrections as needed.