What to Read

Because he was an extremely prolific author, it can be a bit daunting deciding where to start with Crowley's writing, especially if you are not familiar with his style, which can be obtuse and confusing to the uninitiated.  Often you need to know Crowley's style to be able to read his works, because they tend to require you to read between the lines as much as understand the words themselves.  Some of his stuff is more accessible to those new to Crowley and most of it isn't - and he wrote it that way deliberately.

An aside note to start this off is that this is my opinion; I'm sure other Crowley enthusiasts would make a different list all together.

About Crowley Himself

If you're interested in learning more about Crowley's life, a nice place to start might be The Aleister Crowley Scrapbook, which includes essays, photographs, poetry, newspaper clippings and other things revolving around Crowley's life.  Then read The Confessions of Aleister Crowley. It's both accessible and entertaining, if quite long, and has the added bonus of being in print and easy to get a hold of.  There are also three volumes of Crowley's diaries published, at least one of which is in print. 

Fiction & Poetry

His Simon Iff stories are probably the most accessible; they are collected together in the volume The Scrutinies of Simon Iff.  Of his two serious novels, Diary of a Drug Fiend is more accessible than Moonchild, as the latter makes liberal use of Crowley's magickal training.  All of those are in print and easily obtainable. 

Much of Crowley's poetry is out of print and hard to obtain.  Publishers have concentrated on reprinting his religious, magickal and occult works over volumes of his poetry.  However, you can read a number of his poems at this site on the web.

Erotica

Crowley's erotic novel, Snowdrops from a Curate's Garden, is out of print and much harder to obtain - remember inter-library loan is your friend.  Snowdrops is an interesting read, and worth it if for no other reason than most of the original print was destroyed in 1926 by British Customs. 

I find Crowley's White Stains, a book of erotic poetry he originally published in 1898, to be the better read of his erotica.  It was also banned and most of the original print run destroyed by British Customs.  While it was reprinted by Duckworth in 1986, it is also since gone out of print, so inter-library loan is your friend again.  The poetry is beautiful, if you can agree that beauty and filth can exist together.  However, don't even consider White Stains if you are easily offended, for it has been called "the filthiest book of verse ever written" and the poetry therein deals with all sorts of perversions, from sodomy to pederasty to bestiality to necrophilia.  Highly recommended.  :) 

Magickal & Religious Works

If you're interested in Crowley's magickal/religious works it might be good to start with Magick Without Tears.  A kind of magickal instruction book, Magick Without Tears was written near the end of Crowley's life, after his insights, ideas, and knowledge had some time to coalesce in his head.  It's also one of the most easily accessible of Crowley's magickal works - remember what I said above about reading between the lines. 

The Holy Books of Thelema is an excellent buy, as it brings together the core works of Crowley's Thelema philosophy in one volume that is actually quite affordable.  It includes The Book of the Law, which is by far the most important of Crowley's works. 

A good companion for that is The Law is for All, which is Crowley's commentary on The Book of the Law

While Magick is by far the best magickal text ever compiled (again being several of Crowley's works brought together), the 'big blue brick' (as some have dubbed this edition) is not a beginners text by any means, and is rather expensive (though worth every penny). 

Tarot

Crowley's Thoth tarot deck is a beautiful, expressive and esoteric deck, and I use it almost exclusively for tarot working.  I find it to be the most versatile deck I've worked with and it adapts to any kind of ritual or reading. 

The Book of Thoth is worth buying as a companion to the deck, but you might want to pick up the very slim volume Tarot Divination first and work with the deck for a while before you get it. 

 

Do what thou wilt shall be the whole of the law.
Love is the law, love under will.

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