50. The Five Doctors 20.23
While the link that brings all of these characters together is loose at best, because honestly, the idea of the current Gallifreyan president needing ultimate power is a might silly, the more than dozen cameos of past companions, fun combination of villains, and host of self referential references are absolutely delightful. It more than any other story in Classic Who is Doctor Who celebrating itself. Making the case for The Five Doctors is difficult because it is the second anniversary story. However, I think anniversary spectaculars like the one we've had this year would not be possible without an effort like the Five Doctors in Doctor Who's past.
49. Doctor Who: The Movie
There are a lot of reasons to dislike this movie as a Doctor Who story: The cheesy homages to the legend of Excalibur and Frankenstein, the nearly awful portrayal of Eric Roberts as the Masterno offence meant to fans of Mr. Robertsand as far as canonical changes are concerned, there is this awful line of dialogue "I am half-human on my mother's side" uttered by the Doctor at one point. However, the Eighth Doctor himself is worth sitting through all of that. This Doctor is gregarious, and buoyant, so completely in love with life and all its wonders. Which in light of what we now know about the Last Great Time War makes things truly heartbreaking. The plot of this film itself offers us the brutal death and difficult regeneration of the Seventh Doctor into the Eighth. Due to circumstances surrounding the regeneration, he starts his own regeneration with a bad case of complete amnesia, and therefore lagging behind in recapturing a once-again escaped Master. Yet, even while an amnesiac, the Doctor is clearly a Doctor. It is also notable, as most now know for being the first snog between the Doctor and anyone else. While the existence of other Doctor Who mediathe Big Finish audio productions and original novelsallow us other ways of meeting the Eighth Doctor, an hour and a half is not that painful to see his inaugural appearance. Grace, the Doctor's companion, is also likeable enough. But, if nothing else, appreciate that it was bad enough to do poorly in America. Otherwise some set of Americans would have been in charge of Modern Who, and there would have been none of the amazing actors and adventures we appreciated in the last truly great eight years.