Liberalism is so pervasive in modern politics that it can be hard to see as a specific tradition with founders, arguments, and internal fights. It is not simply the opposite of conservatism or a synonym for the political left. Reading in order helps because the twentieth-century debates, especially the great Rawls-versus-Nozick clash, only sharpen once you have the classical foundations and can watch the tradition split into rival branches.
Start with the classics, move to the modern reformulation, then hear the critics from within and beside it.
The classical foundations
Begin with Second Treatise of Government, John Locke's argument for natural rights, consent, and limited government, the deep root of the liberal tradition. Then On Liberty, John Stuart Mill's defense of individual freedom and free thought, which remains the most quoted case for tolerating dissent. For the economic strand, Capitalism and freedom, Milton Friedman's argument linking markets and political liberty, and The constitution of liberty, Friedrich Hayek's systematic statement of classical liberalism.
The modern reformulation
Modern liberal philosophy was reset by one book. A theory of justice, John Rawls' monumental argument for fairness through the veil of ignorance, redefined the field, and his later Political liberalism reworked it for a diverse society. Its greatest challenge came immediately: Anarchy, State, and Utopia, Robert Nozick's libertarian rebuttal, defends a minimal state and property rights against Rawls. Reading them back to back is the core of modern political theory.
Critics and context
The tradition kept examining itself. Liberalism and the Limits of Justice, Michael Sandel's communitarian critique, questions liberalism's picture of the unencumbered self. Two concepts of liberty, Isaiah Berlin's classic essay distinguishing negative from positive freedom, clarifies what liberals even mean by liberty. The liberal tradition in America, Louis Hartz's argument that America was born liberal, and Why Liberalism Works, Deirdre McCloskey's spirited defense, round out the picture.
Read in order, you watch a living argument, not a settled creed. Follow the full path to take the books in sequence.