The Hobbit illustrated by Where the Wild Things Are creator Maurice Sendak? It almost happened, but didn't, and all because J.R.R. Tolkien got miffed, putting a stop to what might have been the greatest edition of The Hobbit ever.
In the late '60s, Sendak was asked by the U.S. publisher to illustrate the novel's 30th anniversary edition, but before Tolkien, then 75, would approve the project, he asked Sendak to audition with a few drawings. This apparently miffed the artist, but he went ahead anyway and created two sketches, one of them (above) of Gandalf and Bilbo.
But when the publisher sent the pieces, the second of which pictured wood-elves in the moonlight, for Tolkien's approval, a mistake was made, as Tony DiTerlizzi over at Hero Complex found out:
The editor mislabeled the samples, however, identifying the wood-elves as "hobbits," as Sendak recalled to Maguire. This blunder nettled Tolkien. His reply was that Sendak had not read the book closely and did not know what a hobbit was. Consequently, Tolkien did not approve the drawings. Sendak was furious.
The publisher tried to repair this misunderstanding, even going so far as to set up a meeting between the two while Sendak was touring the U.K. in support of Where the Wild Things Are, but the day before their meeting, the artist suffered a major heart attack.
He recovered, but no meeting ever took place, and the project was abandoned, killing a masterpiece that might have been ... and now that we've found out about it, breaking our hearts.