I read The Hobbit first, which I'm glad I did. It's a good introduction into FotR -- especially understanding how Bilbo got the ring. The whole birthday party scene would probably be a little confusing had I not read The Hobbit beforehand. It's also a good introduction into understanding Middle-earth. The trilogy is hard if you're trying to break into all that for the first time. The Hobbit was written as a children's book, so I think it's definately much better read first. Then, children who liked The Hobbit when young can get into the Trilogy as they get older.
As for the Silmarillion, I think it is better read
after the Trilogy. First of all, it doesn't really have a storyline -- it's basically a history of Middle-earth. Secondly, it's harder than the Trilogy literary-wise. Thirdly, those who read it without first reading the Trilogy will probably miss out on ALOT. I think that the Trilogy is a good lead up to the Silmarillion in that reading the Silmarillion would be the next step -- much like reading the Trilogy would be the next step after the Hobbit.
Wow, that was confusing. Let me put it this way. The Hobbit is at the easiest level of Tolkien's Middle-earth works. I'd say that the Trilogy would be best read after that and it's level of difficulty would be above the Hobbit. The Silmarillion is sort of like a notch above the Trilogy? Savvy?
Those who read the Trilogy first without reading the Silmarillion are missing out on some things. But, the first time you read the Trilogy, there's alot of stuff to take in. It has enough depth without the Silmarillion. I'd say, once you've taken in most of the stuff from the Trilogy without the initial background in the Silmarillion -- then you're ready to get even deeper into Tolkien's writings about Middle-earth.
And, if you get through all that and
still want to read more -- The Lost Tales and all the rest of the Histories and stuff are good to start reading. 8)
