The good thing is that you can pick any of them up and enjoy them, even those with intimidating or boring-sounding titles likes Knowledge and Decisions.

It really depends on what you are interested in. If economics, then start with Basic Economics, and follow with Knowledge and Decisions, and Applied Economics

If culture, then the Culture triptych is a good start, along with Ethnic America.

If you are interested in the pernicious effect of authoritarian and arrogant elites on society, then Vision of the Anointed, Quest for Cosmic Justice and Intellectuals and Race and Intellectuals and Society.

Black Rednecks and White Liberals is perhaps more accessible, because it's several longer essays which do not rely on one another. Discrimination and Disparities is also one of the shorter works, but which makes a powerful argument. Housing Boom and Charter Schools are also shorter, but I was less interested in those, and less able to evaluate their quality.

It's actually hard to say, because his works are a beautifully ordered whole. Many themes from one area he uses in another, and the result is quite charming.