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“Smiling Paul”, as a meme, is an exploitable image macro featuring a man driving a boat. It first appeared on 4Chan’s /b/ board on February 22, 2012, with OP asking “/b/ – Can anyone photoshop a hot girl beside me here to make my girlfriend jealous?”.
Hilarity and many shoppings ensued, as the smug, self-prideful look on his face can serve as either mischeivous, happy, “swag”, or a variety of purposes at the content producer’s will.
The original thread [NSFW] posted to 4Chan’s /b/ board is here.
Here, the man’s name is revealed as Paul, and one of his friends tells him “keep smiling, Paul”, thus giving the macro the name.
The first reddit thread was submitted, actually referenced within the 4Chan thread, where the user posted a picture of Smiling Paul on the Millennium Falcon. He was probably karma whoring, because he claimed to actually know Paul IRL.
Afterwards came another post, on the 4Chan subreddit, where OP wanted to start a Smiling Paul thread.
As it turns out, Smiling Paul is also a YouTube personality as well, having a few songs and videos uploaded there, in addition to his own blog.