A couple years ago I tried reading the Philosophical Investigations and remember being disappointed. I had the impression of a mind continually strangling itself exactly at the point where it ought to start thinking. Wittgenstein famously was not very well-read in the history of philosophy. This relative ignorance has become part of his legend: rather than be burdened by what everyone else had to say on the subject, he was able to cut directly to the actual problems of philosophy.
At one time I found this very appealing, and no doubt it's true that excessive learning can lead to stale pedantry, an inversion of the real priorities of thought. Nonetheless, I now think erudition is an indispensable part of philosophy. The fact is there's really no escaping our tradition. If we lack a deep understanding of it we are bound to unconsciously fall prey to its prejudices.
Thus in the end I think Wittgenstein's lack of learning was really a liability. He simply didn't go as a deep as other great twentieth century philosophers. And yet he's undoubtedly the most revered thinker of the past hundred years. An aura of awe surrounds practically everything he said or did. This awe cuts across different schools of philosophy, and outside philosophy itself, to art and literature. Partly it's justified: Wittgenstein was a brilliant man, with a mysterious personality, and a seductive, highly quotable prose style.
At the same time for me it's refreshing to find an extremely intelligent author who's willing to puncture this awe. Ernest Gellner devoted a large part of his intellectual career to being the anti-Wittgenstein, starting with his very first book Words and Things published in 1959 (a fun bit of trivia: this book was the reason Foucault's Les Mots et les Choses needed a new name in English, thus becoming The Order of Things).
Published posthumously in 1998, Language and Solitude was Gellner's last book (and also just happens to be the first I've read). In many ways a curious work, it's a genre is not always clear. It begins with a discussion of the fundamental dichotomies of western thought since the enlightenment. On the one hand, we have the atomistic worldview of the isolated individual; on the the other, the collective world of culture and tradition. Or else, we could speak of romanticism vs. positivism, or even language vs. solitude.
From there, oddly enough, the book becomes an account of the decline and fall of the Habsburg empire. Gellner tells this story through intellectual portraiture, taking Wittgenstein as the embodiment of the dilemmas of a decadent civilization. Wittgenstein of course had not one but two philosophies; the first one laid out in the Tractatus, the second in the Philosopher Investigations and other later writings.
Gellner claims that the two philosophies correspond to the basic polarities of western thought. In his first phase, with the Tractatus, Wittgenstein formulated an extreme version atomistic/empiricist view; he then found this to be inadequate and went over to the other extreme, declaring there was no truth outside language and culture. Gellner argues that W was never able to tolerate any ambiguity or mediation between the two views; he was an all-or-nothing thinker. Gellner thus has to bring in Malinowski to give an example of how these polarities can be combined. An empiricist in terms of method (credited with inventing anthropological fieldwork), Malinowski nonetheless developed a non-atomisitic, holistic conception of culture.
Gellner's reading of the Tractatus is wonderful. He has a fine sense of both the philosophical nuances and the human drama of that work. His discussion of the later Wittgenstein is perhaps overly dismissive (even to a non-Wittgensteinian). He doesn't hide his contempt for the vapidness of ordinary language philosophy. However, I'm willing to tolerate the man's crankiness simply for the range and originality of his thought. Gellner was polymath intellectual who wasn't afraid to be polemical, and I hope to keep reading him.