Of all the villains in the Buffy verse the only one that I never felt any sympathy from was Caleb and the First, it seemed that they had very definitely chose to be what they were. However the two that I always felt had really had a bad lot was Drusilla and Darla. Of all the evil characters on both shows, Drusilla is by far the most tragic. In fact it can be said that of all the vampires on the show, only Drusilla and William were genuinely good people, but in the end William made the choice to be a vampire and becomes spike. Dru on the other hand was mentally tortured for a year and then when she finally is about to find some peace in her life she is made a demon, and mad. Its also quite certain that Dru clearly remembers her family and is haunted by those memories. Darla makes the list because of what Angel says, she never had a chance to be a good person. She kept getting thrust into these roles that she could not get out of, and would end up being a puppet to people more powerful then she was. First in her human life she was a prostitute without any real choice in the matter, and then she becomes a vampire and is always the Master's creature. Finally when she is resurrected she is terminally ill, and the only way out that she sees is to become a vampire again. So I always thought that Darla and Drusilla had the worst lives of any of the evil people on Buffy or Angel.