A few books I’ve read recently (and some not so recently) about randomness, probability, human behavior, ALL of which are worth looking at:

Fooled by Randomness by Nicholas Taleb. Instant classic, the followup Black Swan is great too but this is better IMO.

The Drunkard’s Walk: How Randomness Rules Our Lives by Leonard  Mlodinow. Great stuff, some great examples and overall I enjoyed it very much - good lay pieces on probability and misunderstandings around that.

Here are some others I recommend highly:

Predictably Irrational:The Hidden Forces That Shape Our Decisions

Mistakes Were Made (But Not by Me): Why We Justify Foolish Beliefs, Bad Decisions, and Hurtful Acts
Traffic: Why We Drive the Way We Do (and What It Says About Us)

Awesome stuff, all.