In 1 Chronicles 5:2 (KJV) I have found what might be the earliest emoticon; I think the placement is kind of humorous (I have included a bit of 5:1 for context):
…and the genealogy is not to be reckoned after the birthright. For Judah prevailed above his brethren, and of him came the chief ruler; but the birthright was Joseph’s:)
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