Small Beginnings

A question nobody ever asks me is, "Mr. Wickham, you've listened to a hell of a lot of Doctor Who plays by Big Finish Productions, where do you think I should start?" I find the company's own list of recommendations quite baffling in several places, so I thought I would make my own, providing examples for each Doctor. (Most of these items are usually put on sale at least once a year, so keep an eye out.)

FIRST
The Lost Stories - The First Doctor Box Set: The first time BF put Carole Ann Ford and William Russell together, realising two unproduced scripts originally written in 1963.
The Transit of Venus, The Rocket Men and The Sleeping City: A selection of dramatic readings performed by William Russell.
The Bounty of Ceres, The Ravelli Conspiracy and The Dalek Occupation of Winter: I think any BF story featuring Steven Taylor is exceptional. The company seem incapable of producing a bad story with Peter Purves in it. But a lot of them are part of wider arcs and don't work so well as standalones (and I'll try to avoid those here, assuming you're just looking to pick up one or two stories), so if you just want to dip your toe in the water then these are good ones to try from the Early Adventures range (a mixture of fully dramatised and narrated elements). I'd also recommend Return of the Rocket Men and Upstairs.

SECOND
The Selachian Gambit, The Jigsaw War, The Yes Men, The Outliers and The Wreck of the World: A good selection of Companion Chronicles and Early Adventures. (I also really like The Black Hole, but I'm not sure how well it works if you're very new to BF.)

THIRD
Of the four volumes of Third Doctor Adventures with Tim Treloar in the part of the role, Volume Two is unquestionably the best, although Volume Three is the only one I would advise you to steer clear of (Volume One is OK but not great, and Volume Four features one rather good story and an okay story that's marred by being a bit too long.)

From the Companion Chronicles, I would recommend Find and Replace (although some awareness of who Iris Wildthyme is is probably necessary), The Many Deaths of Jo Grant, The Last Post, The Scorchies, Council of War and Ghost in the Machine.

FOURTH
The Lost Stories boxset is great, but perhaps prohibitively expensive at full price. The Fourth Doctor Adventures are a Marmite range, to say the least, but some good choices are The Renaissance Man, The Wrath of the Iceni (pure historical), The Auntie Matter (an excellent pastiche of Wodehouse), and if you're willing to stretch to two CDs, The Paradox Planet / Legacy of Death.

FIFTH
Spare Parts is the one people rightly always mention, but it is a very bleak story, and why listen to all the all-time classics first? The Kingmaker is a great piece of comedy (as is 1963: Fanfare for the Common Men), Circular Time is lovely, but I think the best place to start is The Fifth Doctor Box Set, which features two of BF's most utterly convincing recreations of a television era.

SIXTH
The Wrong Doctors is thoroughly entertaining; 1963: The Space Race is off-the-wall bonkers but tremendous fun; but to go way back to the beginning, Whispers of Terror is a great take on this Doctor's original TV era, and The Marian Conspiracy is a great historical story that introduces the first (and some say best) audio companion, Evelyn (although be advised it is the beginning of a very big story arc that also requires quite a few Seventh Doctor stories to make complete sense of).

SEVENTH
The Harvest also eventually ties into that arc, but is a good jumping-on point by itself, and the next few stories with new companion Hex are generally pretty great (although maybe not Dreamtime). The Novel Adaptations range is also a good place to look.

EIGHTH
An obvious choice, maybe, but McGann's first ever BF story, Storm Warning, is probably the best place to start; if you enjoy it you'll probably enjoy the next few stories. If you don't mind spending a bit more then the Eighth Doctor Adventures range is persistently enjoyable across its four series (if you only want to try one or two, then maybe start with Max Warp or Brave New Town).

THE NEW SERIES
This is currently a bit thinner on the ground, but the Doctor Chronicles range isn't at all bad, and will tide you over until the day they can get the new series Doctors themselves into the studio. But the obvious place to go are the full-cast Tenth Doctor Adventures, which are consistently great (apart from Cold Vengeance), with the current stand-out being Death and the Queen.

SPIN-OFFS
Jago & Litefoot is, in my view, the most consistently brilliant thing ever to be released under the Doctor Who banner. Try the 'pilot episode' The Mahogany Murderers; if you like it, you'll also like the full-cast series (the very first episode of which is free to download).

Counter-Measures is also great, but has been cancelled due to low sales which I'm still very sad about, so maybe if you all buy it it'll come back (its first episode is also available as a free download).