Despite his recent surge in the polls, Herman Cain has always been one of this year’s most controversially verbose GOP presidential hopefuls. Whether he’s breaking out in song at the National Press Club, or making inappropriate jokes about Anita Hill amid charges that he sexually harassed at least four women, Cain’s lack of an internal—or external—censor has been one of the most entertaining, if stomach-churning story lines of this year’s campaign. His rhetorical zig-zagging on how, why and if race matters has been particularly hard to follow. Here are some of his most memorable moments—so far.

*This post has been updated since publication.

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