The one which sticks with me most recently, aside from all the absurd cases since 2000, is the corporate funding case, aka Citizens United.
I started doing some searching, and came across this NYTIMES Book Review article, which reviews Professor Ronald Dworkin's "Decision That Threatens Democracy." For the record, of all the professors I ever learned about when it came to law, Dworkin was always the most impressive.
Anyway, I'd suggest reading the article if you have a moment. Really sheds light on what this court, and largely, what many citizens in this country believe in.
In Citizens United, the Court imposed a heavy burden of justification on the government, and required solid evidentiary support for all justifications that the government offered. For example, the Court rejected as insufficiently supported by evidence the government’s argument that unrestricted corporate expenditures could lead to corruption of politicians, despite extensive congressional findings and evidence documenting precisely such corruption.It gets better...
By contrast, in Humanitarian Law Project, the Court upheld the material support law based on justifications that were unsupported by evidence—and in some instances were not even advanced by the government. The Court reasoned that speech advocating peace and human rights might “legitimate” a designated terrorist group, thereby interfering with US foreign policy. And even though neither Congress nor the administration ever suggested as much, Chief Justice Roberts speculated that advising an organization on how to file human rights complaints with the United Nations might permit the group to use the law to “threaten, manipulate, and disrupt,” and that helping a group pursue peace might give it cover to prepare for its next attack.
Professor Dworkin's take.