The selection of essays, based on, or motivated by "The Matrix" was collected by Open Court Publishers and released in 2002 as "The Matrix and Philosophy" - Vol. 3 in the series "Popular Culture and Philosophy".
I must admit, that the book was very long on my list waiting for me ... I was afraid it was rather superficial account on quite superficial philosophical motives in The Matrix. But the book surprised me very positively. First and foremost, the authors whose essayes are in the book are really distinguished philosophers. Let me only name few: William Irwin, Jorge Garcia, Theodore Shick or Slavoj Zizek from about 20 names.
Second - the authors mostly took The Matrix as the inspiration of some deeper philosophical analysis. These analysis are very interesting and serious, but what is the most important is the very fact that it is for some iconic genre movie that ignited the fire of millenia long dilemmas.
It is impossible in short review to analyse the actual thoughts and polemicize with them.
There are fantastic passages about Platon's alegory of the Cave, about Rene Descartes "Devil" or about Kant forms of perception. All these parables can be found in The Matrix.
Let me, however, look closer at the article "Popping a Bitter Pill: Existential Authenticity in The Matrix and Nausea" by Jennifer L. MacMahon. She analyses the transition undergone by main characters of The Matrix (Neo) and Sartre's "La Nauseé" (Roquentin). In both cases is is about authenticity. The sudden act of awareness reveals, to both of them, though in different way - the true nature of existence. Let me quote:
" ... both The Matrix and Nausea illustrate that authenticity is difficult not only because the truth it reveals is hard to stomach, but also because inauthenticity is the norm. They attribute the prevelance if inauthenticity both to psychological resistance and social indoctrination. As Roquentin's and Neo's experience make evident, the true nature of reality is not necessarily something humans want to see."
This parallel of The Matrix to La Nauseé is especially meaningful to me, because it was the later Sartre novel that was important part of my philosophical awakening, more than 30 years ago, and start for life-long philosophical search....
The another worth mentioning essay is "Real Genre and Virtual Philosophy" by Deborah Knight and George McKnight. It is very important because it uncovers how many of The Matrix philosophical motives could rather be attributed to specific genre it is deeply rooted. In some sense the authors unmask the true inspirations of The Matrix. According to them, they (inspirations) are more for The Matrix being a very good emanation of specific Genre, than for true philosophical convictions of its authors. BTW, the authors of the essay try to map The Matrix onto famous Northrop Frye classification of modern genre, and they argue for The Matrix belongs to ... Romance.
The general conclusion from reading the Book is that, while The Matrix itself is certainly not philosophical fairy-tale and is full of contradictions and serious philosophical simplifications - it still was an ignition for much bigger and much deeper philosophical discussions ...