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A Broader Perspective on Ayn Rand and Objectivism
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Reason and Value: Aristotle versus RandReason and Value: Aristotle versus Rand by Roderick T. Long
Buy new: $14.78
Places Rand's thought in the context of various philosophical traditions.
The Philosophic Thought of Ayn RandThe Philosophic Thought of Ayn Rand
Buy used from: $2.31
Collection of hit or miss essays on Rand.  The essays by King and Matson are good jumping off points for reflection.
Ayn RandAyn Rand by Tibor R. Machan
Buy used from: $18.50
Solid introduction on Rand by a philosopher who is sympathetic to many of her ideas, but not uncritically so.
On Ayn Rand (Wadsworth Philosophers Series)On Ayn Rand (Wadsworth Philosophers Series) by Allan Gotthelf
Buy new: $15.95 / Used from: $0.57
Accurate, but dry, introduction to Rand.  Good example of how Rand's ultra-fans view her.
Ayn Rand: The Russian RadicalAyn Rand: The Russian Radical by Chris Matthew Sciabarra
Buy new: $35.95 / Used from: $4.99
Probably the best book written about Rand.  Valuable even if you don't agree with Sciabarra's thesis.
The Contested Legacy of Ayn RandThe Contested Legacy of Ayn Rand by David Kelley
Buy new: $21.95 / Used from: $11.90
An Objectivist philosopher takes a nuanced view of Rand and Objectivism.
Universals: An Opinionated Introduction (Focus Series)Universals: An Opinionated Introduction (Focus Series) by D. M. Armstrong
Buy new: $32.25 / Used from: $15.94
Contra Rand, the question of universals is a metaphysical problem.  This book will help you undo some of Rand's confusion.
Ayn Rand, Objectivists, and the History of PhilosophyAyn Rand, Objectivists, and the History of Philosophy by Fred Seddon
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There is no satisfactory book on Rand's philosophy of history.  This is an okay place to start.
New Individualist ReviewNew Individualist Review by New Individualist Review Journal
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Contains Bruce Goldberg's scathing critique of Rand's (mis)understanding of other philosophers.
Grounding for the Metaphysics of Morals: With on a Supposed Right to Lie Because of Philanthropic ConcernsGrounding for the Metaphysics of Morals: With on a Supposed Right to Lie Because of Philanthropic Concerns by Immanuel Kant
Buy new: $7.95 / Used from: $0.75
Don't trust the Rand/Peikoff caricature of Kant's ethics.  Read him for yourself (and in only 62 pages).
Economic Science and the Austrian MethodEconomic Science and the Austrian Method by Hans-Hermann Hoppe
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Libertarian economist and philosopher defends Kant's epistemology in the face of Randian-like criticisms.
The Making of Europe: An Introduction to the History of European Unity (The Works of Christopher Dawson, 3)The Making of Europe: An Introduction to the History of European Unity (The Works of Christopher Dawson, 3) by Christopher Henry Dawson
Buy new: $20.26 / Used from: $14.13
Rand had an extremely negative view of Christianity and religion.  The works of Dawson will serve as a good correction.
Evidence of the Senses: Realist Theory of PerceptionEvidence of the Senses: Realist Theory of Perception by David Kelley
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The best book by an Objectivist philosopher.  Ignored by Official Objectivists because (in part) Kelley's views in The Contested Legacy.
The Reliability of Sense PerceptionThe Reliability of Sense Perception by William P. Alston
Buy new: $22.95 / Used from: $14.70
Doesn't discuss Rand, but mentions some arguments used by her.  A good example of how certain topics in philosophy are a bit more complex than Rand believed.
Objectivism and the Corruption of Rationality: A Critique of Ayn Rand's EpistemologyObjectivism and the Corruption of Rationality: A Critique of Ayn Rand's Epistemology by Scott Ryan
Buy new: $20.65 / Used from: $29.44
Best critique of Rand.
Ayn Rand Contra Human NatureAyn Rand Contra Human Nature by Greg Nyquist
Buy new: $21.55 / Used from: $18.89
Critiques Rand's view of human nature.
Without A Prayer: Ayn Rand and the Close of Her System (Trinity Papers No. 50)Without A Prayer: Ayn Rand and the Close of Her System (Trinity Papers No. 50) by John W. Robbins
Buy used from: $12.48
Another hit or miss book on Rand.  Good discussion of Rand's lack of originality on certain issues.
The Ayn Rand CultThe Ayn Rand Cult by Jeff Walker
Buy used from: $6.64
Type of book about Rand that I can't recommend.  Collects a lot of material, but hard to distinguish wheat from chaff.
The Passion of Ayn RandThe Passion of Ayn Rand by Barbara Branden
Buy new: $12.21 / Used from: $1.98
Hard to evaluate biography of Rand by a follower who had a falling out with Rand.  Fortunately the two biographies of Rand in preparation will render it obsolete.