Rory (Spoilers from Angels Take Manhattan)
Don't read if you haven't seen the Doctor Who episode, Angels Take Manhattan, and plan to.[blank] [blank] [spoilers!] Rory Williams is the boy who died…and died…and died again! It's almost a "you killed Kenny" running joke in the show. So much so that the Silence makes a joke about it in The Wedding of River Song. I've tried to count his deaths in the "real" world and in imagined or faked alternatives, some of which were later collapsed.
- Mrs Poggit kills him in Amy's Choice (dream)
- The Doctor blows up the T.A.R.D.I.S. in Amy's Choice (dream)
- Shot by Restac, a Silurian in Cold Blood (real)
- Erased from universe in Cold Blood (more of an extension of being shot and killed)
- "Shot" by Canton in Day of the Moon (fake)
- Drowned and revived in The Curse of the Black Spot (real)
- Found as skeleton by Amy in The Doctor's Wife (illusion)
- Died of old age in The Angels Take Manhattan (real, but later erased in paradox)
- Jumps off building in The Angels Take Manhattan (real, but later erased in paradox)
- Died of old age in The Angels Take Manhattan (real, and final)
Did I miss any? Angels is particularly amusing in having him die thrice.