Recommend me some mind expanding thought provoking existence questioning films/tv/books!

For a great introduction to philosophy give him Sophie's World by Jostein Gaarder. It deals with the history of philosophy and what we can and can't know about ourselves and the world in a very accessible format. The story constructed around Sophie is a bit meh but the philosophy discussions are excellent.

Here is the wiki page http://en.wikipedia.org/wiki/Sophie%27s_World
 
To add to my previous recommendations - pretty much anything by John Wyndham is worthwhile.
Ubik by Philip K. Dick (he of Do Androids... fame) although I'm sure that he has many others worth reading.
Slaughterhouse 5 by Kurt Vonnegurt is also an entertaining and thought provoking book.
If you're happy to provide some lighter material then Ender's Game by Orson Scott Card is good too.
 
Terence Malick films (new one out very soon that won the Palm D'or, The Tree of Life). Russell's A History Of Western Philosophy and The Consolations of Philosophy are good primers, Zen & The Art of Motorcycle Maintenance, Man's Search For Meaning, there's loads.

If he's into sci-fi then Iain Bank's Culture books are always worth a shot.
 
The Doors of Perception by Aldous Huxley

Buckethead albums COLMA and Shadows Between the Sky

Any David Lynch films, they are all masterpieces (other than Dune)

Kubricks 2001 and Solaris by Tarkovsky
 
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Film:
Manhattan
Lost In Translation
War Photographer
Children of Men
Grave of The Fireflies
Studio Ghibli/Miyazaki films
Wall-E


Literature:
Shakespeare's plays (The Tempest is my favourite I'd say, but they're all amazing)
Norwegian Wood by Murakami
Poetry/Essays by Percy Bysshe Shelley (Queen Mab, Ozymandias, The Necessity of Atheism)
Poetry by W.B Yeats
Poetry by W.H Auden
Poetry by T.S Eliot (Prufrock, The Waste Land, The Hollow Men)
A Day in The Life of Ivan Denisovich (nice and short, quite uplifting in a strange way)
World War Z (yeah it's got zombies, but it's also an interesting exploration on human nature and society)
Gulliver's Travels (biting satire that still rings true today)
The Grapes of Wrath
The Great Gatsby
Lolita
The Buddha of Suburbia
Some Thomas Hardy (Tess of the D'Urbervilles and Jude the Obscure are my favourites)


Music:
Radiohead
Pink Floyd
Godspeed You! Black Emperor
toe
Led Zeppelin
Sigur Ros
Bjork
Deltron 3030
Madvillain - Madvillainy
Gil Scott Heron
Bob Dylan
 
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