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Fanfiction is somewhat of an uncharted territory, which few actual writers/critics take serious note of or are very enthusiastic about. It has been long asked and established whether publishing fanfics is even legally possible at all. Yes, it is possible as long as the work in question doesn't violate copyrights and the plot line isn't too dependent on the original novel it was inspired from. But has there been cases where works that count as fanfiction to some degree have been literally successful and turned out as bestsellers?

Of course, I understand that it isn't very fruitful or wise either for a budding writer to work in this genre. One will just be wasting their time and talent. I just want a list of the exceptional fanfic bestsellers that have managed to do reasonably.

Why wouldn't it be possible?

Yes. Fifty Shades et al are Twilight fanfics. Note that you may have to reskin a work (change characters, names, settings, etc) to get far enough away from the original work.

Let's try this again: Is Sherlock Holmes on the BBC fanfic? Yup.

For a while, Amazon ran a program called Kindle Worlds where writers could write "fanfic" within the world of subscribed authors (Hugh Howey's Wool series, for example) within certain original author-established parameters. I wrote and published a story in that system, and it sold better than I expected (several hundred copies, maybe), and I had, over the course of a few years, a couple hundred extra dollars. No bestseller, but I can see how one could come out of a situation like that.

The main obstacle to fanfics flooding the market is copyright. As long as the original author holds the copyright for their work, fanfics can only live as free stuff on the internet. (Or, as Kirk points out, they can be "reskinned", "retooled", so they're not obviously recognisable as fanfic. In which case, it all depends on how good your lawyers are compared to the lawyers of the original writer.) I personally think that making money off somebody else's work in this fashion is sort of stealing. Cervantes notably was extremely unhappy about someone publishing a Don Quixote fanfic, and went on to publish his own Don Quixote II, in which he mocked the fanifc. But such moral considerations are beside the point.

Once the copyright is over, the work you wanted to write fanfic about is either long forgotten, in which case the fanfic loses its point, or it's become a classic, in which case jusgement of your fanfic is going to be rather harsh: what can you, unknown modern writer, add to the time-honoured classic? Such works do exist, but are less common.

And then, when a work is old enough, it turns out that yes, you do have something to add to it. Enough time has passed that retelling the same story in a different way is now original, interesting, respected, literary. Once and Future King and Mists of Avalon are both Le Morte d'Arthur fanfics. Ursula Le Guin's Lavinia is an Aeneid fanfic. Except that at this point they are no longer called fanfics.

What differentiates your run-of-the-mill fanfic from works like Once and Future King or Wide Sargasso Sea that you mention, is that the former aim mostly at producing more of the same, with some measure of insert-fic and/or doing things to the original book's romances. Whereas works of the latter kind seek to engage with the source material, and using it, say something new, unique. In this fashion, they outgrow the "fanfic" definition.

Wide Sargasso Sea comes to mind.

It cannot exactly be considered a fanfic, given that it was a direct result of the writer's disagreement with Bronte's unflattering portrayal of a certain Creole character. Madwife Bertha of Jane Eyre is almost antagonistic, in the sense that it is one of the forces that hold the titular protagonist from fulfilling her dreams and hopes.

But it can certainly be called a "rip-off" (for the lack of a better word) of Jane Eyre, based on one of the central characters from the same. (The storyline doesn't rely too heavily on Jane Eyre though.) And it's a classic in that and can be thought of as a bestseller by extension. I don't suppose the messages and themes in it would have been too popular in those times and that they would have sold either. But it is not unheard of now and definitely critically acclaimed and a fine piece of work in my opinion, serving as an elegant response (or you could see it as a payback) to the subtle literary degradation of the Creole people.