If he likes the Dead get him the book "Electric Kool-Aid Acid Test" by Tom Wolfe. It's a true story about the whole acid party/hippie scene in San Francisco during the late '60's. Some of the Grateful Dead's first concerts were playing the Acid Test parties, and they're brought up several times in the book. The thing about this book is, although it's a true story it's written like a novel, not just a history book or collection. For example, people like Jerry Garcia, Ken Keysey, and Timoty Leary are actual characters in the book not just names. So, it's really an entertaining read.