Here is Steuard Jensen definitive recommendation on what books to read about Middle-earth!

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Keep in mind that the suggestions that follow for parts to look forward to and parts you may want to avoid are just educated guesses; don't read too much into the exact order in which they are listed. Positive recommendations are ranked from best to worst; negative ones from worst to best.
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The Hobbit: A wonderful story, and an important introduction to Middle-earth.


The Lord of the Rings (often published in three volumes: The Fellowship of the Ring, The Two Towers, and The Return of the King): Most find ths to be the best of Tolkien's writings about Middle-earth. It captures all the beauty and excitement and sorrow and glory of classic epic tales while casting them into a truly original form, and describes its world of Middle-earth so vividly that it seems almost real. The book manages to touch on substantial questions of ethics and philosophy seamlessly within the narrative, without discussing them directly or attempting to push some agenda.

Because the tone of The Lord of the Rings changes substantially over the course of the first ten chapters or so, I generally suggest that people try to finish all of Book I (the first half of The Fellowship of the Ring) before giving up. If you aren't interested by that point, then I'll admit that Tolkien probably isn't right for you (not yet, anyway). As an additional piece of advice, it's probably best to skip the Prologue entirely the first time you read the book, although if you haven't read The Hobbit it would be worth reading Section 4: "Of the Finding of the Ring" (it, like the rest of LotR, contains spoilers for the earlier book).


The Appendices and Prologue of The Lord of the Rings: Listed separately because they are a rather different experience than LotR itself. The different types of writing in the various appendices give a reasonably good sampling of what can be found in Tolkien's other books about Middle-earth.

Parts to look forward to:
App. A.I.v: The Tale of Aragorn and Arwen
App. A.I-II: Gondor, Arnor, and Rohan
App. A.III: Durin's Folk
App. F: Languages, Peoples, and "Translation"

Parts you may want to avoid:
App. C: Family Trees


Unfinished Tales: A collection of tales and partial stories whose final state Tolkien never settled upon. Many of these are extremely good, and make me wish that Tolkien had made greater progress toward their completion. In addition to the enjoyable stories themselves, this book provides a wealth of information and many tantalizing hints about Middle-earth and its history, both within the tales and in a number of fascinating essays.

While the first part of this book deals with the First Age and almost requires that you have read The Silmarillion first, much of the rest of it (especially the Third Age stories) can be read immediately after The Lord of the Rings. (The independent nature of these stories and essays makes it easy to read them in any order.) Unlike The Silmarillion, it is also a good introduction to the style of the "History of Middle-earth" books, with Tolkien's writing thoroughly annotated by his son Christopher. (It's easy to skip the annotations if you aren't interested.)

Parts to look forward to:
Aldarion and Erendis
The Quest of Erebor
The Disaster of the Gladden Fields
The Hunt for the Ring
The Istari [Best enjoyed after reading The Silmarillion; then, ranks above "The Hunt for the Ring".]
The Druedain [Best enjoyed after reading The Silmarillion; then, ranks above "The Hunt for the Ring".]

Parts you may want to avoid:
Narn I Hin Hurin [Best enjoyed after reading The Silmarillion; then, ranks above "Aldarion and Erendis".]
Of Tuor and his Coming to Gondolin [Best enjoyed after reading The Silmarillion; then, ranks above "Aldarion and Erendis".]


The Silmarillion: Tolkien's lifework, edited and published posthumously by his son Christopher. Somewhat biblical in style at the beginning (perhaps in part because Tolkien never had the chance to rewrite it in more narrative form), it contains the entire history of Middle-earth from its creation to the end of the Third Age. This is the last book about Middle-earth to have a single, coherent storyline, which makes it essential for a good understanding of the First Age.

Although most of the events described in The Silmarillion took place thousands of years before the time of The Lord of the Rings, it is almost certainly best to read LotR first, for several reasons. First, LotR is written as a novel, while much of The Silmarillion reads like a history book. Second, many readers enjoy the glimpses of Middle-earth's history that are mentioned in LotR because they are just glimpses; it's probably good to experience that at least once before you fill in all those gaps. Finally, the last section of The Silmarillion actually includes a plot summary of LotR filled with spoilers.

Parts to look forward to:
QS Ch. 19: Of Beren and Luthien
QS Ch. 21: Of Turin Turambar
Ainulindale
The Quenta Silmarillion in general
Akallabeth
Of the Rings of Power and the Third Age

Parts you may want to avoid:
Valaquenta
Genealogies
Appendix: Elements in Quenya and Sindarin Names


The Letters of J.R.R. Tolkien (ed. Humphrey Carpenter): While this is not technically a book by Tolkien about Middle-earth, a great many of the letters that it contains discuss various Middle-earth related issues. Their topics include Tolkien's comments and speculation while writing his stories, the publication process, details about Middle-earth not covered in the other books, and speculation on the deeper issues raised by the tales. (There are also quite a few letters that deal primarily with Tolkien's personal life and beliefs, which are interesting in their own right.)


The Book of Lost Tales, Parts I-II (HoMe I-II): These books contain Tolkien's earliest writings about Middle-earth and its history, and they include some incredibly vivid and beautiful stories and scenes. The tales themselves are told in the context of a framing story about an early English sailor who stumbles upon Tol Eressea. Be warned that it can be quite difficult to follow these tales, as they differ substantially in detail and in general from the corresponding stories in The Silmarillion and The Lord of the Rings and they are often not in finished form. Only Christopher Tolkien's commentary on the stories assumes knowledge of The Silmarillion; for the stories themselves, having read that book can make this one at once more and less confusing.

Parts to look forward to:
II: The Fall of Gondolin
II: The Tale of Tinuviel
II: Turambar and the Foaloke

Parts you may want to avoid:
I and II: Appendices on Names


Morgoth's Ring and The War of the Jewels (HoMe X-XI) ("The Later Silmarillion"): These books contain Tolkien's latest work on The Silmarillion, including the texts from which the published version was primarily compiled. They also include a number of fascinating essays, showing entirely new directions that Tolkien was considering taking the mythology and shedding light on many details of Middle-earth and its history. Despite this, the books would be very hard to follow on their own: reading The Silmarillion first is all but essential.

Parts to look forward to:
XI: The Wanderings of Hurin
X: Athrabeth Finrod Ah Andreth
X,XI: The Later Quenta Silmarillion
X: Myths Transformed


"Osanwe-kenta: `Enquiry into the Communication of Thought'" (Published in the Tolkien linguistics journal Vinyar Tengwar #39 (July 1998), which is available for $2 at the Elvish Linguistic Fellowship website): A truly remarkable essay (associated with "Quendi and Eldar" in The War of the Jewels), discussing the "telepathy" possessed by all "incarnates" in Middle-earth, ways in which the Ainur could become "bound" to their physical forms, and the moral decisions of Manwe regarding Melkor. (This issue of Vinyar Tengwar also contains a passage omitted from App. D of "Quendi and Eldar" as published, of primarily linguistic interest.)


Sauron Defeated (HoMe IX): The first third of this book is "The End of the Third Age", the conclusion of "The History of The Lord of the Rings" subseries, including the unpublished epilogue to LotR. (Note that this is also mentioned under the entry for that subseries as a whole.) The final two thirds consists of early writings related to Numenor. "The Notion Club Papers" is an abandoned but substantial draft of a fascinating "dream-based time-travel" story connecting members of a discussion group in the present day (based loosely on the Inklings, a group including Tolkien, C.S. Lewis, and others) to their ancestors in Numenor. "The Drowning of Anadûnê" is more or less a retelling of the Downfall of Numenor from the perspective of humans many years later when they had forgotten the nature of the Elves and the details of their history. It's an amazingly different perspective (some of which survived into the "Akallabeth" in the published Silmarillion.

Parts to look forward to:
The Notion Club Papers
The Epilogue (of LotR)
The Drowning of Anadune
Lowdham's Report on the Adunaic Language

Parts you may want to avoid:
The End of the Third Age


The Lays of Beleriand (HoMe III): The existing fragments of Tolkien's poetic versions of the stories in The Silmarillion, which can be beautiful and powerful in some places and wearying in others. Those reading this book before The Book of Lost Tales should be prepared for substantial confusion at first: most of these poems were written when the mythology was very different than the version in The Silmarillion, and both the poems and the commentary may be difficult to understand without being familiar with both of those books.


The Peoples of Middle-earth (HoMe XII): This book is divided into three main parts. The first is a history of the writing of the Appendices and Prologue of The Lord of the Rings. The second is a collection of significant essays written late in Tolkien's life. The final section contains the abandoned beginnings of two stories, one about a man in Second Age Middle-earth who meets the returning Numenorians and the other a sequel to LotR itself.

Parts to look forward to:
Of Dwarves and Men
The Shibboleth of Feanor
Last Writings
The New Shadow

Parts you may want to avoid:
The History of the Akallabeth
General History of the Prologue and Appendices to LotR
[Writing of] The Appendix on Languages


Pictures by J.R.R. Tolkien and J.R.R. Tolkien: Artist and Illustrator (the latter edited by Wayne G. Hammond and Christina Scull): I have not actually seen the first of these, which I believe is very much what the title proclaims it to be: a collection of Tolkien's drawings. The second is also a collection of his pictures, but with a fair bit of commentary about the drawings' history and style. Many, but not all, of the pictures are related to Middle-earth.


The Lost Road (HoMe V): This book contains a very broad range of content: the earliest versions of the tale of the Fall of Numenor (including early work on a "time travel" story based on that theme), the state of the mythology at the time that LotR was begun, and the Etymologies which are of great value to those interested in the Elvish languages.

Parts to look forward to:
The Lost Road
Etymologies
The Lhammas

Parts you may want to avoid:
The Later Annals of Valinor and Beleriand
Quenta Silmarillion
The Second 'Silmarillion' Map


"On Fairy Stories", published in Tree and Leaf (Often most easily found as part of The Tolkien Reader (USA), which also contains "The Adventures of Tom Bombadil", or The Monsters and the Critics and Other Essays (Commonwealth), both of which also contain a number of Tolkien's writings not related to Middle-earth.): Technically, this essay has absolutely nothing to do with Middle-earth at all: it is a fascinating but (mostly) academic discussion of the form and purpose of fantasy, and those seeking storytelling should look elsewhere. However, in one section of it Tolkien makes numerous references to "elves" and the Art that they create: for example, "To the elvish craft, Enchantment, Fantasy aspires." In the essay, he does not treat the elves as "real", but nevertheless it seems that his comments on elves here do apply to the elves of Middle-earth.


The Road Goes Ever On (music by Donald Swann): A collection of poems and songs from Tolkien's writings set to music. Almost all of the poetry is all available in other books (primarily The Lord of the Rings), and the music is mostly Swann's work without substantial input from Tolkien himself (Tolkien did approve of the music, however, and he suggested the theme for the Namarie). However, Tolkien contributed substantially to the book, providing direct translations of the songs in Elvish languages and even some "story-internal" historical notes. The second edition of this book (1978) incorporated the short poem "Bilbo's Last Song", which is now also available as a small book illustrated by Pauline Baynes.


The Adventures of Tom Bombadil (Often most easily found as part of The Tolkien Reader (USA) or Tales from the Perilous Realm (Commonwealth), which both also contain quite a few of Tolkien's writings not related to Middle-earth.): A collection of poems, supposedly traditional Hobbit verses from the Red Book, together with a preface relating their history in the Shire. Many of these poems existed before The Lord of the Rings was written and were only later revised and brought into the mythology (indeed, the two poems about Bombadil were part of the inspiration for his character in the book rather than the reverse).

Parts to look forward to:
Preface

Parts you may want to avoid:
Other Poems (3-16)
Bombadil Poems (1-2)


"Guide to Names in The Lord of the Rings" (Published in early editions of A Tolkien Compass, ed. Jared Lobdell. Recent reprints of the book omit the Guide, making it very difficult to find.): A document that Tolkien wrote to assist those translating The Lord of the Rings into other languages. It explains the source or meaning of many of the names in the book, and includes a few pieces of non-linguistic information about Middle-earth as well.


Tolkien: The Authorized Biography (by Humphrey Carpenter): As might be expected, this book does not deal directly with Middle-earth. However, it contains a great deal of information on Tolkien himself, which can in turn shed light on Middle-earth (and give more insight into the textual history in HoMe).


The History of The Lord of the Rings (HoMe VI-IX) (usually published in four volumes: The Return of the Shadow, The Treason of Isengard, The War of the Ring, and either the first third of Sauron Defeated (listed elsewhere) or the separate volume The End of the Third Age): These books track the development of LotR through many drafts from its origins to its final form. Watch as Trotter the hobbit turns into Strider the human, as an adventure to replenish the dwindling Baggins fortune turns into a quest to save the world, and as dozens of story elements seem to come as even more of a surprise to their author than they do to us. Some of Christopher Tolkien's notes indicate places where the published text seems to have deviated unintentionally from the final drafts. The final book includes the unpublished Epilogue to LotR. (Note that this is also mentioned separately under Sauron Defeated.)


The Shaping of Middle-earth (HoMe IV): The earliest development of Middle-earth as a world in its own right. In addition to the earliest sketches of what would become The Silmarillion, this book contains some of Tolkien's earliest maps of Arda, including his only hints at extrapolation beyond the area shown on the usual maps of LotR (make sure you find a copy that includes them! Some paperback editions leave them out).

Parts you may want to avoid:
The Earliest Annals of Valinor and Beleriand
The First 'Silmarillion' Map
The Earliest Silmarillion

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