Master

Oldest known vampire, permanently stuck in vamp face
1609: Sired a prostitute suffering from syphilis, named her Darla
1800: Sired the Slayer, Yuki Makimura, who served him from Japan for many years
1936: Imprisoned within a mystical barrier when trying to open Sunnydale’s Hellmouth
1996: Broke through the barrier after drinking the Slayer, Buffy Summers, blood; again attempted to open the Hellmouth
1997: Staked by Buffy, left behind a skeleton
2007: Restored by the Seed of Wonder, killed by Angel