Reddit mentions of Basic Writings (Harper Perennial Modern Thought)

Much like you, I've also recently developed a strong interest in Levinas. I've yet to read him, though, so please take that into account when considering my recommendations.

I recently asked some of my professors and a friend of mine who wrote his master's thesis on Levinas to help me out with getting started. This is what they recommended:

• This introductory book by Colin Davis has been the most recommended to me. Davis succeeds in the difficult task of executing a clear exposition of Levinas' difficult prose without sacrificing too much of its nuance.
  
• Regarding Levinas' own writing, begin with On Escape. This work develops Levinas' fundamental ideas on Being and alterity, demonstrates how he does phenomenology, and reveals his engagement with Heidegger and Husserl
  
• The two next best works to read are Existence and Existents and Time and the Other.
  
  I'm not too knowledgeable of Husserl, so all I can really recommend from him is the Cartesian Meditations, which sort of serves as an introduction to Husserl's own method of phenomenology.
  
  For Heidegger, the most important work in this regard is certainly Being and Time. If you have the time, I recommend picking up the Basic Writings and reading through most of it.
  
  On a final note, Levinas was steeped within the Jewish intellectual tradition. Jewish philosophers often emphasize the role of community and social contextuality in general. It might serve you well to read works such as Martin Buber's I and Thou and Gabriel Marcel's Being and Having.
  
  EDIT: Another good compliment to Levinas is Maurice Merleau-Ponty's Phenomenology of Perception.

I'm in a similar boat as you; interested in continental, but surrounded by a lot of analytics.

Hegel is notorious for being dense and difficult to read, and while he was incredibly influential on many later continental thinkers, I don't think anyone who really wanted to help you get into continental philosophy would have you start on Hegel, unless they were committed to reading through it with you.

Heidegger's maybe a bit less obtuse at times, but he can also be confusing if you don't have a professor or more experienced student guiding you along. I asked a professor where I should start, and he recommended his published lecture notes from The History of the Concept of Time, which I admittedly haven't finished yet, but he spends a lot of time in it explaining Husserl's philosophy of phenomenology, which is crucial for understanding Heidegger, as well as a number of other continental thinkers.

As for some easier continental-esque thinkers, there are some that I think are a bit more accessible. Bear in mind that there isn't exactly a group of thinkers who all signed a document saying they were continental philosophers, but there are a number who seem to run in the tradition, and many others who were at the very least related to them.

To begin, I'd recommend some Kierkegaard. He was a Christian philosopher, and is often considered to be one of the earliest existentialist philosopher's. He did a number of works on concepts of faith, anxiety, dread and other elements of the human condition, adding his own angles on them to apply them to Christian philosophy. He wrote under a number of pseudonyms in order to create a number of different perspectives, although underlying all the chaos was a desire to get you to start thinking for yourself. A good place to start with him would be Fear and Trembling. Many of his ideas were influential on continental thinkers such as Heidegger, Jaspers and Sartre.

To go in a very different direction, Nietzsche is another thinker who was very influential on many continental philosophers. The self-declared Anti-Christ, he basically believed that we are about to enter a post-God world, with his writings often either trying to burn our bridges back to the Church or trying to point us in a new direction. Like Kierkegaard, he doesn't always say what he means directly, but much of his philosophy is ultimately aimed at getting you to start thinking for yourself. I'd recommend this anthology, as it contains a number of pretty crucial writings of his.

If after this you're still interested in Heidegger, I don't have as much background there, although I've read a few of his Basic Writings, which is a collection of essays of his. In one of my classes, we also read an essay from his Pathmarks which wasn't terribly dense, so that might be a nice place to start as well. Being and Time is generally considered to be his most important work, but it's renowned for being dense and difficult, although there are a number of commentaries on that book alone that may prove useful.

For one final recommendation, I'll throw in Kaufmann's anothology of existential writings, which has a number of essays on existentialism, which was heavily tied to many core continental thinkers.

And I wouldn't worry about your roommate.

Martin Heidegger's Basic Writings (an anthology of his work). Some pretty mind bending philosophy that will challenge your view on "Being".

Life as Literature by Alexander Nehemas and Nietzsche as Philosopher by Arthur Danto are my some of my favorite secondary Nietzsche works.

When you move on to Heidegger... Heidegger's writing style is super difficult to parse and I prefer him in smaller bits. I would recommend his essays in the Perennial Basic Writings compilation if you haven't checked it out yet.(https://www.amazon.com/Writings-Harper-Perennial-Modern-Thought/dp/0061627011)

Try to read some of his lectures like "Was ist Metaphysik?" or "Vom Wesen der Wahrheit". I am sure there are english translations of these as well.

EDIT: "Was ist Metaphysik?" can be found in English in the bundle of texts called "Basic Writings" (for example: http://amzn.com/0061627011) which serves as an excellent introduction to Being and Time.

One of the most insightful things I've read on technology is Martin Heidegger's essay "The Question Concerning Technology." I'm on a mobile and it's the middle of the night, so I'm not going to go on at length (about a favorite topic of mine.) It's the attitude that goes with technology's domination, of other ways of seeing the world, that is a danger more than the technological artifacts themselves, he thought. Niel Postman has written about similar things (without mentioning Heidegger that I remember) in Technopoly. I don't worry about technology, though I am concerned by technocracy. THX 1138 is a great movie, and I've felt strongly that it's an apt metaphor for what life has been like as a software developer, for me.

[edit: I'm on my computer now, so sky's the limit...]There's a Star Trek: The Next Generation episode in which a people has a relationship to high technology that seems unusual to Captain Picard. They don't let it dominate their lives. They use it, but they don't live in a technocracy. They live in what seem like rural surroundings.

Philosophy of technology can have a dystopian twist to it, especially the little I've read that has been "Continental." I love dystopian stories. I have no solution but to read, read, read, real stuff about technology and our relation to it. Heidegger points out that it is not a thing but an attitude, as I've said. "The essence of technology is nothing technological," to quote him as well as I can. I firmly believe the solution to establishing a healthy relation to technology is to take other points of view -- other than the currently dominant (in the US) technocratic view -- and find out what they are. Phenomenology for me is right where it's at. I will understand it in my lifetime! xD If you can find these books at the library, they're ones I've read recently. Reading them may not be completely encouraging, and yet they'll take your mind off worries about the technological doodads and what they're doing. Just reading the book is a whole-body activity, it's so hard.

Heidegger's "Basic Writings" collection (paperback is cheap https://www.amazon.com/Writings-Harper-Perennial-Modern-Thought/dp/0061627011)
After you've read Heidegger's essay, "The Question Concerning Technology," Don Ihde's little book is a gem
Heidegger's Technologies: Postphenomenological Perspectives (https://www.amazon.com/Heideggers-Technologies-Postphenomenological-Perspectives-Continental)
Neil Postman's "Technopoly"
William Barrett's "The Illusion of Technique"

Perhaps "going back in time" to the earlier of these will allow a little distance from your current concerns. Seeing that technology has been viewed as problematic, by smart people, for many decades, is comforting to me. Another book that really slammed everything, it seemed, home for me, was Herbert Marcuse's "One-Dimensional Man," which channels a lot of the frustration of Lucas' film. Finding another way, finding people who see differently than the company they work for does, if it makes paper clips, for example...to the paperclip company, everything has to do with making and selling paperclips. Nick Bostrom had a few funny things to say about a possible supersentient AI whose mission was to make paperclips, in the podcast (wonderful!) "The Partially Examined Life" (iTunes and http://partiallyexaminedlife.com/).

I gripe about how much of our communication is digitally mediated. Here I am on the Internet, speaking of the evils of technology. Ironic? I think a little story about Freud is in order here, then. When Freud observed that the train could take him to see his niece(?), who lived far away from Freud, he saw that this could be viewed as an argument against any of his objections to "progress"; but, he said, without the train she never would have been so far away in the first place. Without the Internet, I might spend more time talking with people face to face. It has always been one of my favorite things to do, in spite of all difficulties. It just seems so difficult now because so many people's faces are constantly pointed at screens instead of each other.

If you want the highlights with the goal of understanding late Merleau-Ponty, I recommend Husserl's "Philosophy as a Rigorous Science" and the Cartesian Meditations, Heidegger's Basic Writings especially the first three chapters but then any others that interest you, some of The Phenomenology of Perception, and maybe "Eye and Mind". I then recommend skipping to the Chiasm chapter of The Visible and the Invisble before reading the whole text.