Mind blown.
The first twenty minutes or so, I was afraid this was going to be a really dull film (I already knew the whole premise was two guys having a conversation for nearly two hours), but I ended up mesmerized. In fact, when the movie ends, I ended up feeling a little let down because I wanted the conversation to keep going!
I'll also admit that, like SeanMX12, it was the episode of Community that got me interested in seeing this movie in the first place.

My Dinner with Andre is an amazing, layered piece of work. On the surface, just a conversation between Wallace Shawn and Andre Gregory playing shades of themselves (which is also part of the conversation, dipping into postmodernism) in seeming real time, the more I think about it, the more those other layers manifest. Over the course of this dinner, the two diners discuss experimental theater, mysticism, science, love, living and dying, and as such is an obvious inspiration for such beloved films as Before Sunrise, though it does not appear any less fresh, and politically, still resonates today (1981 and 2017 have the same dystopian concerns). But when you reflect on the order those topics come in, and how Andre the Jodorowskian mystic (his vivid stories are so insane, you've got to laugh) goes on non-stop for the first two thirds or more of the film, another story unveils itself, that of the human race. In Andre's zen experimentalism, I felt the inertia of the ancient world and its ritualistic superstitions - there's a reason his first story is about non-verbal men and women in the woods - and in Wally's anxious humanism, arriving late to defend the comforts of home and the ambitions of individualism, we have the modern man, rejecting the unproven and finding purpose in the little things, crashing into the conversation in a panic, admitting to nagging ties to superstition, and fearful of Andre's nihilistic contentment. The conversation ends with death, as great stories must. Two people sitting, talking and very occasionally eating, and yet it feels like an epic philosophical struggle. Pay attention to the sound design for more layers. Feels like something one should revisit at different times in one's life, if only to see with which character one most agrees - Wally? Andre? Or the waiter?

a film about life itself. i been left stunned by the depth of the film both times i've seen it and think i'll watch it once a year for the rest of my life. a masterpiece