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Here's a question I've been pondering. I occasionally run into somebody who loves the current Doctor Who series, and wants to check out the classics, but finds the selection kind of daunting. I'm not sure what to recommend, because I have my favourites, but I have a hard time narrowing the list down to one or two, and then I'm not sure if they're really the best introduction to the show. On the one hand, I know episodes that just exemplify the whole series, and I know some that show the variety and diversity of themes, characters and styles that were used over the years. Different Doctors, companions, writers, producers all brought a different flavour to the show, and it went through distinct periods where one element or another was emphasized. And I find I like many of them for different reasons.

So, that's the question. Assuming we're dealing with somebody who can appreciate the old show for what it is, what would you recommend? Pick two or three serials, try to include a bit of variety, and share your reasons.

I'll also see if I can pare down my list to a handful of choices, and explain why I like them.

Hmm hard to narrow it down so very much given as you pointed out there's such a variety of Doctors and companions to choose from but I think personally I'd probably go with the following:

The Sensorites: an intelligently written story about an alien species the Doctor (William Hartnell) encounters that not quite the usual but really shows a lot of what the Doctor is all about. This one had a very intriguing realism I felt going for it in that the aliens were not all alike but each seemed truly an individual.

The Tomb of the Cybermen: Probably my personal favourite. So much great stuff here that predates stuff used similarly later especially with Star Trek: TNG's The Borg. There are some similarities to Quatermass here too I feel with this one. Really enjoyable stuff. Doctor here was Patrick Troughton.

The Ark in Space: should at least appeal to horror fans and features the Doctor (Tom Baker) dealing some some rather nasty alien beasties. I found it to be pretty exciting and suspenseful.

The first episode I ever saw was Terminus, with Peter Davison.  That was enough get me hooked on the show, so I guess it would be my recommendation for a newcomer.  Cheesy as can be but it's got a great cast of characters and the plot is crazily awesome.

Another favorite is Horror of Fang Rock with Tom Baker.  Cheesy little horror story set in a lighthouse with excellent characters and one of the most spectacularly silly endings imaginable - just what I love about Dr. Who.

To give the classics a fair chance, I think where possible I'd tend to go with story arcs following specific characters, or single eps introducing what become 'regulars'.

The Second Doctor's "Tomb of the Cybermen" is great.

The Third Doctor introduced The Master. Any of those stories are good background.

The Fourth Doctor's “Key to Time” arc has a good plot, good pacing, an effective companion and scripts by Douglas Adams.   
The Fourth Doctor episode "Genesis of the Daleks" is a particularly good one for both background and for itself.

I think the Fifth Doctor should be fairly palatable for those who are 'into' the newer regenerations.  That might ease them into it a bit.

Definitely agree with Genesis of the Daleks. It pretty much set up all subsequent Dalek serials, and it was a good story.

I think City of Death is a great example of all the elements of Doctor Who that have become the foundation of the new series. We have a story taking place at multiple points in time, an alien in human disguise secretly manipulating events on Earth, humans experimenting with dangerous technology, evil schemes to be figured out, historical figures acquainted with the Doctor, and consequences that ultimately affect all of humanity. The Doctor himself is at his most disarmingly eccentric and erratic, always on top of things but still having a blast until he really has to get serious. It also has a humorous temporary companion and a celebrity cameo.

The Brain of Morbius is another one that is just a fun episode, and a good example of the gothic horror phase the show went through in the Tom Baker years. And it has one of the coolest monsters.

I agree with the episodes featuring Roger Delgado as the Master. The Third Doctor episodes also give some nice background on UNIT.

Tomb of the Cybermen is definitely a good one, and possibly the best of the Troughton episodes that are still intact.

For an overall introduction, The Three Doctors is pretty good, with Hartnell, Troughton and Pertwee all in character, highlighting their similarities and differences. It also has UNIT playing a major part, and involves the Time Lords and some of their history.

Either The Two Doctors, or The Five Doctors. Not my favorites but a good basis for introduction. If seeing an Androgum chef trying to cook and eat Peri and Jamie doesn't hook someone, they're hopeless.

I must respectfully disagree with The Five Doctors, as it's more suited for established fans. My brother-in-law tried to introduce his stepbrothers to Doctor Who with that one and it was a colossal failure. It's better to go with something a bit more self-contained. Tomb of the Cybermen is certainly a good choice.

That's what I was thinking. You get to see five doctors and several companions, but it's not really an introduction so much as a treat for those who already know them.

Avoid fan favorites and look for stories that introduce characters and events mentioned in the new series. As much as I love TALONS OF WENG-CHIENG, you probably wouldn't enjoy it if you'd never seen Tom Baker's Doctor before. I would suggest these:

SPEARHEAD FROM SPACE
It explains how the Doctor joined Unit and introduced the Autons.

GENESIS OF THE DALEKS
The origin of the Daleks is told and the introduction of Davros.

THE DEADLY ASSASSIN
Has a lot of background on Galifrey and the Time Lords and is very suspenseful.

TIME WARRIOR
Introduces the Sontarans and Sarah Jane Smith.

TERROR OF THE AUTONS
More Autons, introduces The Master and Jo Grant.

LOGOPOLIS/ CASTROVALA
Not great stories, but if your really into the regenerations Logopolis has the best one of the old series. Castrovalva really shows the turmoil a new Doctor goes through after regenerating.

CAVES OF ANDROZANI
Not only does it have a regeneration, it shows the Doctor at his most heroic as he faces his mortality. Arguably this is the old Doctor Who story that is most like the new series. More action and faster paced than other episodes of the time.

Don't go for the multiple Doctor stories until you become an old series diehard. Those stories will confuse new fans. Also avoid the old Cybermen stories, they are a completely different race of Cybermen and it won't give you any insight on the current Cybermen.

The Deadly Assassin is another one I'd been considering. It's a good Time Lord story with lots of background, it has one of the Master's more nefarious plots, and it has that really cool Most Dangerous Game bit in the middle.

I don't really agree with avoiding the Cybermen though. The original Mondas Cybermen are a part of the new show's history. They've been referred to and they've made a couple of appearances. Seeing the originals might provide additional context for fans of the new show, and they are not so different from the Cybus Cybermen that they'd confuse anyone. As long as it's understood that they are the original Cybermen from our universe, thought extinct by the time of the new series.

I was also thinking maybe The Seeds of Doom. Good, Earth-based story, with the government calling on the Doctor's unique expertise. It's got a dangerous alien species gaining a foothold on Earth, aided by an insane millionaire. Lots of action, suspense, close calls, explosions and fairly complex characters. It's also one of the last original UNIT appearances. Overall, it's very similar to what we see in the new series. Plus, it has a definite John W. Campbell influence, with the alien discovered in the Antarctic ice, assimilating a human, terrorizing the heroes and eventually threatening to overrun the planet.

The one that came to my mind is the Seeds of Doom story.  It has always been one of my favorites.

It's really hard to suggest what would work for the masses. I really like the Cybermen but the new origin wasn't exactly the way I'd hoped they would come back. It's great to show the internal struggle of man and machine, but the whole parallel universe thing and how it ties in with Rose and Mickey's families doesn't do it for me, sorry. I would have enjoyed a story with a even more of an emphasis on defining the new Cybermen, than a tearjerker (at lest for the introduction, you can always get emotional later on). On further thought maybe suggesting stories that explain the background of certain things wouldn't work so well as the ideal introduction on to the old series. The first episode I ever saw was "Underworld" which isn't very highly regarded, but it made me a fan nonetheless. And as this was my first viewing, I didn't know anything about the characters or anything else in way of a story arc. I just knew liked the adventure. I think the stories that really grabbed me the first time I saw them were "Face of Evil" and "Robots of Death." Both are action driven with characters that have clearly defined personalities (right down to the robots). When I think of Doctor Who I almost always tend to think of those stories with Leela, because those were among the first that I saw. I didn't take long for me to really care about the characters and what would become of them.

I haven't seen much Doctor Who, but I've seen Planet of Evil, and I got the first few episodes for Christmas.  Is that a good starting point?

Planet of Evil is an excellent choice. The Tom Baker stories from his first three seasons are arguably Doctor Who at it's finest. I'm assuming you got the Beginnings boxed set with An Unearthly Child, The Daleks and The Edge of Destruction. It's always good to start at the beginning. Those earliest Hartnell stories had a hard time holding my attention when I first saw them. I like them a lot better now that I'm older and more patient.

I would start with Spearhead from Space. It's getting a Blu-Ray release and it really works both as an introduction to the series or as stand alone serial.

STONES OF BLOOD
SPEARHEAD FROM SPACE

and my personal favorite

CITY OF DEATH with its' great Tom Baker line "Patron! Three glasses of water. Make them doubles."  :teddyr:

It is difficult for me to pick one episode from each Doctor, especially 3-5.

One episode from each Doctor:
Hartnell :   The Keys of Marinus
Troughton:   The Tomb of the Cybermen (I like The War Games, but it is a long story, 10 epiodes)
Pertwee  :   Inferno
T. Baker :   The Android Invasion
Davison  :   Earthshock
C. Baker :   Vengeance on Varos
McCoy    :   Dragonfire

I was a huge fan of the Jon Pertwee, Tom Baker and Peter Davison era Dr Who seasons, but have little love for Colin Baker or Sylvester McCoy, and I have not even seen any of the new seasons, however good they are supposed to be.

What would I recommend for someone to get into earlier era Dr Who?

Jon Pertwee - Terror of the Autons.  This introduces not only the Doctor, but also Delgado's Master, who becomes a supervillain extraordinaire.  Delgado's Master was energetic, egotistical, and often prone to violence, unilke Ainley's Master, who was more subtle and sneering.  Delgado's Master would jump onto speeding army trucks, hypnotise the driver through the window, and smash people into walls.  Ainley's Master, while still cool, had more of the theatrical mustache-twirling feel to him.

As an aside, I wish they had resurrected the Master character as a more energetic and violent villain in the new stories.

Tom Baker - The Pyramids of Mars.  Absolute classic in the Hammer Horror vein, involving ancient alien gods, a creepy mansion and robotic mummies!  Another excellent Tom Baker story is the Seeds of Doom, about an intelligent plant alien that is intent on infecting the entire Earth. 

If your friend wants a whole series of stories, give him The Key to Time sequence which includes The Ribos Operation, The Stones of Blood, The Pirate Planet and the Armageddon Factor.  Not to mention the lovely, and now sadly deceased, Mary Tamm as Romana. 

The Tom Baker stories often had a Hammer Horror gothic feel, including The Image of the Fendahl and The Masque of Mandragora.  If he's into the Hammer stuff, he will like those.  Or if he likes the Cybermen, you can't go past any of the Tom Baker Cybermen stories, they are fab.

Peter Davison - I'd go with Earthshock, or Full Circle.  In fact, many of the Davison era stories were great.  The Black Guardian stories involving Turlough, like Mawdryn Undead, were fascinating and show a lot of character development.

The Robots of Death
(Tom Baker)

I'm with this guy.

http://www.youtube.com/watch?v=P6PMy6gUAHk

Sorry.

Going with one from each Doctor:

Hartnell: The Time Meddler
Troughton: The Web Of Fear
Pertwee: The Mind Of Evil
Baker: Talons Of Weng-Chiang
Davison: The Visitation
Colin Baker: Vengeance On Varos
McCoy: Ghost Light
McGann: the TV movie
Eccleston: The Empty Child
Tennant: Doomsday
Smith: The Doctor's Wife

That statement is slightly misleading. Adams only wrote The Pirate Planet. The others were written by the usual DW writers, like Robert Holmes and David Fisher.

Trailer for the classic WEB OF FEAR:

http://youtu.be/GPm6zcy_6j0 (http://youtu.be/GPm6zcy_6j0)

The Mind Of Evil trailer:

http://youtu.be/EjJBy9mJeCA (http://youtu.be/EjJBy9mJeCA)

Talons Of Weng-Chiang trailer:

http://youtu.be/ST7DALEmSu0 (http://youtu.be/ST7DALEmSu0)

The Time Meddler trailer:

http://youtu.be/tNPBvnWU0g0 (http://youtu.be/tNPBvnWU0g0)

The Visitation trailer:

http://youtu.be/lzc7VeXa3gQ (http://youtu.be/lzc7VeXa3gQ)

Vengeance On Varos trailer:

http://youtu.be/LptcyA-zSnA (http://youtu.be/LptcyA-zSnA)

Ghost Light trailer:

http://youtu.be/iZnJtJX2NgI (http://youtu.be/iZnJtJX2NgI)

The Empty Child trailer:

http://youtu.be/iTQhBNCqKQ4 (http://youtu.be/iTQhBNCqKQ4)

Doomsday trailer:

http://youtu.be/llz6FCsE4Mc (http://youtu.be/llz6FCsE4Mc)

The Doctor's Wife trailer:

http://youtu.be/bZAVJOEGnsw (http://youtu.be/bZAVJOEGnsw)