Classic Who Recommendations

One way to tackle this is to watch stories in order from some suitable starting point. If you can do this approach, you could start at any of the following stories and have a decent understanding of the current situation and follow what's happening:

* An Unearthly Child (1st Doctor, 1st story)
* The Rescue (1st Doctor, Vicki's first story)
* The Tenth Planet / Tomb of the Cybermen (oldest surviving Cybermen stories)
* Spearhead from Space (3rd Doctor, 1st story)
* Terror of the Autons (3rd Doctor, Jo Grant's first story)
* The Time Warrior (3rd Doctor, Sarah Jane Smith's first story)
* Robot (4th Doctor, 1st story)
* The Deadly Assassin (4th Doctor, first story set entirely on Gallifrey)
* The Ribos Operation (4th Doctor, Romana's first story)
* Mawdryn Undead (5th Doctor, there's no independent starting point for him)
* Vengeance on Varos (6th Doctor, 3rd story)

Really, the best place to start for the 5th Doctor is The Keeper of Traken, which is a 4th Doctor story, but sets up the characters and following events.
The 7th Doctor's run alternates between independent stories and stories that rely heavily on previous stories.

If you want to watch individual stories across the whole of Classic Who, giving the "flavor" of each era, then here are some stories you could watch on their own.

* The Aztecs (1st Doctor, original crew, historical)
* The Time Meddler (1st Doctor, semi-historical)
* Tomb of the Cybermen (2nd Doctor, base under siege)
* The Mind Robber (2nd Doctor, experimental)
* The Claws of Axos (3rd Doctor, experimental)
* The Time Warrior (3rd Doctor, semi-historical)
* Pyramids of Mars (4th Doctor, gothic)
* City of Death (4th Doctor, Douglas Adams)
* Kinda, (5th Doctor, experimental)
* Mark of the Rani (6th Doctor, semi-historical)
* Greatest Show in the Galaxy (7th Doctor, on location)

Some of the stories will feel as though they're tied into some larger picture, but they really aren't. Each has different Companions and gives a general "flavor" of the era in which it was made.

Ok, I'm no expert because I've only seen most of these once but I'll give it a try.

I find 3's era interesting. He's not my favorite Doctor, and it's not my favorite era, but there are so many really great stories that I always feel that I contradict myself when I say that. Spearhead From Space, The Silurians (a must), Inferno, Terror Of The Autons, The Deamons, Carnival Of Monsters, The Green Death. These are all great. (And the first 3 are with my favorite 3rd Doctor companion, Liz Shaw)

4: The Arc In Space is one of my favorite 4th Doctor stories. It's Baker's second serial but the first one where he really feels like The Doctor. There are so many must see stories from his 7 years in the role. Genesis Of The Daleks, Terror Of The Zygons, Pyramids Of Mars, The Brain Of Morbius, Seeds Of Doom,The Robots Of Death, Talons of Wang-Chiang, City Of Death. And I've not even named all of the ones I love.

5: I have a harder time recommending stories from this era. Kinda, Earthshock, Enlightenment, Caves Of Androzani (a must)

6: Vengeance On Varos, Revelation of The Daleks (kind of surreal), The Mysterious Planet

7: Remembrance Of The Daleks, The Curse Of Fenric, and I actually really like Survival. I just realized that all of these are really strong stories for Ace. It shows how much I like her as a companion. 

And even though you didn't ask....

1: An Unearthly Child (although I have a very hard time getting through the rest of the cavemen episodes), The Aztecs, The Romans (I don't think it's a fan favorite, but I really like it), The Time Meddler, The Dalek Invasion of Earth

2: (Please don't skip 2. He's terrific and he has some great companions. Plus, there are so few stories of his that survive.) Tomb Of The Cybermen, The Web Of Fear, The Invasion, The Mind Robber (also surreal, but sooo good), The War Games

Whatever you choose, enjoy them!

Well, let's see... Good jumping on points include:

Third Doctor
Terror of the Autons
The Claws of Axos*
The Three Doctors

Fourth Doctor
Genesis of the Daleks
The Robots of Death
The Talons of Weng-Chiang*
City of Death

Fifth Doctor
Earthshock*
Snakedance
Frontios
The Caves of Androzani

Sixth Doctor
Attack of the Cybermen*
Vengeance on Varos
The Two Doctors
Revelation of the Daleks

Seventh Doctor
Remembrance of the Daleks*
Ghost Light
Battlefield
The Curse of Fenric
Survival

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Those marked with an asterisk are what I would probably consider to be imperative jumping on points. Attack of the Cybermen in particular is purpose built to reintroduce the Sixth Doctor to audiences, doing a much better job at establishing who exactly this man is.

wolfie, I'm curious why you didn't list Spearhead From Space as a jumping on point for Three, since it is actually his, well, jumping on point and a really great story? Also, why do you think Axos is imperative? I don't remember it being all that special, but I may be remembering wrong.

Good question. I could say that that The Claws of Axos is a good indicator of the general flavour of the Third Doctor's era as a whole with Axos itself still being a visual marvel even in this day and age, but to be honest I think I might've completely forgotten about Spearhead. You're absolutely right, it's an excellent starting point. The only Doctors I would really advise against starting with their debut story are Old Sixy (because The Twin Dilemma really isn't representative of his character), the First Doctor (because An Unearthly Child is unconscionably dull after the first episode) and the Seventh Doctor (because Remembrance was able to do pretty much everything Time and the Rani couldn't).

Simply in terms of quality and variety:

Spearhead from Space
Genesis of the Daleks
The Robots of Death

Three very different but universally praised stories.

Interesting. I think Season 7 is probably my favorite season of Pertwee's tenure. I know it doesn't have The Master and Jo, which are so heavily identified as part of that era, but I just love The Brigadier in this season, before they started making UNIT completely inept, and Liz.

I haven't watched all that many First Doctor stories and what I have watched from the Second Doctor seasons is scattered. I've only seen An Unearthly Child, The Daleks, and The Dalek Invasion of Earth. Of them, The Dalek Invasion of Earth is probably my favorite - a really grand story, with a very popular speech at the end. From the Second Doctor's era, I've seen Tomb of the Cybermen, The Mind Robber, The Enemy of the World, and The War Games. All of them are absolutely phenomenal stories, but this is especially the case for The War Games. I've also listened to the audio original staging of Power of the Daleks, his first story, and Fury from the Deep, both of which I can definitely recommend.

For the Third Doctor, I heartily recommend his first story, Spearhead from Space. I remember when I originally watched it, I declared it the best "new Doctor" story I had ever watched. Still do, as a matter of fact. After that, The Silurians is pretty good - it's the inspiration for the Silurian two-parter in Series 5 of NuWho, but a lot better in my opinion. Inferno is a stone cold classic. The Three Doctors is a must watch, and Time Warrior is pretty solid as well. The Planet of the Spiders is a pretty enjoyable regeneration story, but not the best - still recommendable.

As for the Fourth Doctor, watch his entire first season, EXCEPT for Revenge of the Cybermen. The Ark In Space and Genesis of the Daleks in particular are amongst my favorite Fourth Doctor stories. The Pyramids of Mars is brilliant and the Deadly Assassin gives you a great look at Gallifrey and Peter Pratt's only performance as the Master. After that, definitely The Talons of Weng-Chaing. I cannot stress how much I adore that story - it's what I immediately think of when someone says "Philip Hinchcliffe." City of Death is my favorite Classic Doctor Who story and easily one of the funniest. I also recommend The Horror of Fang Rock and the Fourth Doctor's final story, Logopolis, which definitely isn't perfect, but it has some great ideas.

The Fifth Doctor, sadly, never really had any stories that just REALLY stuck out to me besides Earthshock and my second favorite Classic Who story, The Caves of Androzani. Most people would recommend Kinda and Snakedance and, since the villain of those two stories is pretty interesting, I think I'll second that opinion - I'll need to give both stories a revisit sometime in the future. The Five Doctors was a pretty good special, too.

Unfortunately, the Sixth Doctor's stories are all a matter of opinion. I personally really liked The Two Doctors, but I have heard several fans who think it's merely alright at best. Vice versa, I've heard a lot of fans who really liked Vengeance on Varos, whilst I think it's just an okay story. The Trial of a Time Lord season has some pretty great moments - and one of the finest speeches from ANY Doctor - but I'd say skip episodes 9 to 12 and just find the edited highlights elsewhere online.

Finally, that leaves us with the Seventh Doctor. His first season is pretty dire, so I wouldn't recommend checking any of his episodes with Mel out, besides Dragonfire, which introduces Ace. After that, though, I'd say check out Remembrance of the Daleks and The Greatest Show in the Galaxy from Season 25, and then ALL of Season 26. I also have a soft spot for The Happiness Patrol in Season 25, so I'd say give it a look if you're curious.