The original and best-known Tolkien song setting is the cycle The Road Goes Ever On, music by Donald Swann. This has been performed occasionally at Mythcons, and this year, tenor Garry Leonberger came to perform it. Leonberger is an enthusiast for Swann's generally neglected serious music, and is writing a doctoral thesis on it, which he summarized in a pre-concert talk.
Leonberger has a strong, clear voice of medium range. His singing emphasized a strong rhythmic accentuation, with a careful attention to diction, especially in the Elvish lyrics, proper pronunciation of which he has studied extensively, likening its vowels to Italian's. (Tolkien linguist Carl Hostetter said from the audience afterwards that Leonberger's Elvish pronunciation was better than Tolkien's own.) There was no breaking of the rhythm or other characterization portrayals except for the spoken-word part of "Errantry". Leonberger told me afterwards that he envisages the songs as being all sung by Bilbo, which is why he didn't try to differentiate his hobbit voice from his elf voice.
The vocals came reasonably through the unpromising acoustics of a carpeted hotel ballroom. No arch to the low ceiling, no reverberation, high absorption. It came out pretty well, even though near the end he began to lose his voice, becoming clouded and rough and losing some of his low notes. Linda James valiantly accompanied on both piano and flute. Swann's style, though pleasantly diatonic, is highly abstract and rather arty. I've heard this cycle sung with more winning informality, but Leonberger gave the music, and its lyrics, great attention and concentration. I hope he comes back next year, as hoped for, in better voice with Swann's other arrangements of the songs, including choral ones, and perhaps professional accompanists and some other Tolkien settings.
After closing ceremonies the next day, our tenor, feeling somewhat better, and Hannah Thomas gave an impromptu performance of the drinking song from La traviata to the general delight.