Chris Petersen, over on Resurrection Dogmatics has compiled a list of his Top Ten Historical Jesus Works. In that vein, here are my top ten (with more than a little overlap).
10) The Historical Jesus: The Life of a Meditteranean Jewish Peasant, by John Dominic Crossan. I think Crossan is wrong with mind-boggling frequency. It's enough to make me wonder if he doesn't actively try to find the wrong answers. But, paradoxically, he's consistently wrong productively, which is probably worth more than being right but not forwarding the discussion.
9) The Message and the Kingdom by Richard Horsley and Neil Asher Silberman. The first time I read this book, I was thoroughly unimpressed. I can in fact remember sending Peter Kirby an email expressing my disdain for it. Then I read it again and wondered "What the hell was I thinking?"
8) A Marginal Jew (3 Vols, 4th hopefully coming along) By John P Meier. Sometimes I think Meier's theology gets the better of him (most notably, of course, in the case of the virgin birth), and while he is best remembered for his contribution to discussion on the Testimonium Flavianum, I ultimately find him unpersuasive on that point. Nonetheless, his series is a must read, belonging on the bookshelf of anyone interested in the Historical Jesus.
7) The Quest of the Historical Jesus by Albert Schweitzer. Much of his argument seems outdated and uncritical by today's standards, but his general model--that of thoroughgoing eschatology--is, IMO, wholly correct. Perhaps his greatest contribution was showing that the Quest of the Historical Jesus frequently amounts to little more than a literary equivalent to Rorschach's inkblots: What we see in the image is ultimately a reflection of self.
6) Jesus After 2000 Years by Gerd Lüdemann. Far more a reference work than a book one might read cover to cover, and standing out on this list in that regard, Lüdemann provides a fantastic resource.
5) The Historical Jesus: A Comprehensive Guide by Gerd Theissen and Annette Merz Declining to offer the more normative, thoroughgoing model of the historical Jesus, Theissen and Merz instead opt to focus on various aspects of Jesus separately, such as "Jesus as Charismatic" or "Jesus as Prophet." An excellent resource for solid background information on virtually every aspect of HJ study--from the history of the "Quest" to the millieu of Jesus.
4) Jesus the Jew by Geza Vermes. Vermes really has no methodology to speak of, and as one who sees methodology as frequently getting in the way of plausibility, I can dig that (far moreso here than in his effort to assess the sayings material in The Authentic Gospel of Jesus, where I couldn't dig it much at all).
3) Jesus of Nazareth: Millenarian Prophet by Dale C. Allison The first of two "Jesus of Nazareth" titles to appear on the list. Allison rejects efforts to obtain a non-eschatological Jesus, writing that "We cannot separate chemical compounds with a knife. Nor can we tell at the end of a river what came from the fountainhead and what from later tributaries" (p. 33). Because of this approach, Allison is able to reverse the normative trajectory. Instead of beginning by establishing historicity of individual traditions, Allison begins with eschatology, and uses that paradigm to assess the evidence.
Ultimately I am hard-pressed to believe that anyone's reconstruction does not follow that trajectory--beginning with a paradigm rather than developing one. Allison stands out because he realizes it.
2) Jesus of Nazareth: King of the Jews by Paula Fredriksen. The most correct book I think I've read on the historical Jesus. Fredriksen answers the question "Why did Jesus die, but his followers didn't," with, IMO, the best explanation offered.
1) I've gotta agree with Peterson for this one. Top spot goes to Jesus and Judaism by E P Sanders. While I might think he's hinged too much on the temple (as is implied by my agreement with Fredriksen), this book is nonetheless requisite. A benchmark of the type few will ever succeed in offering.