The reasons I am so strongly opposed to the NIV rendering of hebel (the Hebrew word translated “meaningless” in Ecclesiastes in the NIV) are as follows:

1. The basic meaning of hebel is "breath." It is, to an extent, synonymous with ruach.

2. Thus, something that is hebel is evanescent, not long-lasting, not having much in the way of substance, impossible to grasp (hence the occasional pairing of hebel with "chasing after wind" in Ecclesiastes).

3. None of those uses argue "meaningless" as an apt rendering for hebel.

My own sense is that "meaningless" for hebel comes from two sources. First, it is (and I am admittedly psychologizing here) an attempt to render "vanity" in modern English, rather than to render hebel in modern English. That is, I suspect the NIV translators were, in part, motivated by a desire to have the modern reader understand the English word "vanity" (so familiar from the KJV), rather than to understand the meaning of the Hebrew word hebel.

Second, I think the rendering "meaningless" has arisen out of a misreading of the book as a whole. Modern evangelical scholars have been too influenced by the idea that Ecclesiastes was (a) influenced by Greek skeptical thought of one sort or another, or (b) that the bulk of the book was written by some heterodox Jew that some orthodox Jew later tried to rehabilitate (though God alone knows why that scenario would produce a book in the canon of Scripture), or (c) that the book, whatever its background and influences, is in its essence contradictory, cynical, skeptical, lacking faith. In that context, perhaps "meaningless" makes a good rendering of hebel, but it has to ignore lexical as well as contextual evidence to do so.

A careful reading of Ecclesiastes would show the reader that the author (Solomon, in my view) is actually using the word hebel in a number of ways, here indicating that something is brief, there indicating that something lacks substance, another place that because of the nature of something as hebel that it produces frustration. In none of those cases is "meaningless" a good fit for the use of hebel.

Finally, there are two NT passages that are intended to inform us regarding the significance of Ecclesiastes (and of hebel). The first is Romans 8:20 "for the creature is subject to vanity" (Geneva Bible). The word translated "vanity" there is the same Greek word used in the Septuagint for hebel. God did not subject the creation to meaninglessness, but to temporariness, to frustration, in order to remind us that "under the sun" is not all there is.

The second passage is James 4:14. I think the significance relative to Ecclesiastes is evident.

Ecclesiaste Commentaries

Recommendations on Ecclesiastes Commentaries

My starting point is the organization of the book, because without a good understanding of how the book fits together, you're almost certain to go wrong at some point. The book is notoriously difficult to outline, however. For this, I would recommend the chapter on Ecclesiastes in David Dorsey's The Literary Structure of the Old Testament. He might not have solved all the problems, but he has certainly solved most.

Then, for good, but brief treatments that can help give you a good feel for the book, I recommend Michael Eaton's commentary in the Tyndale OT series, as well as Derek Kidner's contribution to the The Bible Speaks Today Series, titled A Time to Mourn and a Time to Dance.

For dealing with more technical questions of grammar and syntax, and for critical views, I would recommend Roland Murphy in the Word Biblical Commentary series.

For sermonic helps and good theological understanding, I recommend Charles Bridges, a nineteenth century commentator reprinted in the Banner of Truth Geneva Commentary series..

One further note. I see the book as entirely unified in message and purpose. (In addition I have no trouble with Solomonic authorship, because I don't find the linguistic arguments against it compelling, and those are the only arguments against Solomonic authorship that have much substance.) Since I see the book as a unity, I have real problems with those interpreters who see the book as harboring essential contradictions. Hence, I find such commentators as Tremper Longman, Michael Fox, and Roland Murphy to be unreliable guides. I think Murphy to be not quite as unreliable as the other two. There is in these interpreters an unhealthy skepticism toward the Biblical text that is not only inherently dangerous, but it fails properly to understand the book itself.

P.S. The decision of the NIV to translate hebel (vanity) as "meaningless" has done more to contribute to the common misunderstanding of Ecclesiastes than any other single thing.