| | It's probably too late to add my own suggestion, but in the off chance that it's not...
Here's my recommendation.
I know that many students of Objectivism recommend Atlas Shrugged first, but because it is heavy-handed, it might put you off altogether, and so I would encourage you to save that until later.
1. If you want an illustration of the philosophy, I recommend Rand's The Fountainhead first. It is the best literary work for this purpose. It lacks the Nietzchean aspects and quirky style of Anthem, the pessimism and historical emphasis of We the Living, and the heavy-handedness of Atlas Shrugged.
2. If you want an explanation and analysis of the philosophy, I recommend Sciabarra's Ayn Rand: The Russian Radical. Even if you disagree with Sciabarra's approach, you'll find that he's done his homework and that he includes in his book the views of many (if not all) the major students of Objectivism. Other scholarly works on Objectivism are not as exhaustive as his.
3. Depending on how much time you want to spend on understanding this philosophy, I'd encourage you to read Rand's nonfiction, which stand as the seminal philosophical works that have influenced (or some would say constituted or established) Objectivism: The Virtue of Selfishness, Introduction to Objectivist Epistemology, Capitalism: The Unknown Ideal, and The Romantic Manifesto (in that order).
However, these works can be hard to appreciate on their own. You might have to read the other books to appreciate any one of them, as I think Rand intended her philosophy to be viewed as an integrated whole.
This why I would encourage you to read Sciabarra's book before Rand's seminal nonfiction. He attempts to show that integration throughout.
Jordan
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