I've purposely left Catch-22 off my list until now because I knew it is one of my dad's very favorite books. If you've never read it, you owe it to yourself to pick it up. Funny and alarming at the same time, this satire targets the madness of war, bureaucracy, politics, and mass hysteria.
It's dark and heavy thematically, but genuinely brilliant and cleverly farcical. It caused a stir when it was released and was both praised as one of the greatest books ever written and condemned for its negative views.
This book is always included on numerous best book ever lists, usually in the top twenty, so I think it's stood the test of time, outlasting all detractors. If you are a fan of Dr. Strangelove, this is certainly the book for you.