There's one from way earlier in a source you wouldn't have imagined. The King James version of the Bible, in 1611 has an emoticon in I John 1:2 2(For the life was manifested, and we have seen it, and bear witness, and shew unto you that eternal life, which was with the Father, and was manifested unto us;)
2(For the life was manifested, and we have seen it, and bear witness, and shew unto you that eternal life, which was with the Father, and was manifested unto us;)