Currently in the queue: Adcult USA by James Twitchell, Executive in Action by Peter Drucker, The Fall of Berlin by Anthony Read.
Without further delay, here are some books that are worth reading more than once.
Anything by David Ogilvy
Anything by Edward Tufte
Anything by Richard Wurman
Almost anything by Marshall McLuhan
The Design of Everyday Things by Donald Norman
1984 by George Orwell
Writing that Works by Roman and Raphaelson
Being Direct by Lester Wunderman
Being Digital by Nicholas Negroponte
Where the Suckers Moon by Randall Rothenberg
Microserfs by Douglas Coupland
On the other hand, I have wasted too many hours with overhyped books expecting to get something out of them. The latest ones that come to mind are Clement Mok's Designing Business and The New MaxiMarketing by Rapp and Collins. Damn them.