Why it took off, I have no idea. I always preferred 'There are spiders in my hair! There are spiders in my hair!' response from The Asylum (at Georgia Tech, I think), unfortunately, that site closed shop in the 1990's, and most people these days never saw it. They had a poll archive, but I can't remember the exact URL to check if archive.org has a copy of it. (and searches for the above response or 'favorite features of Microsoft Bob' don't find anything)
The asylum had an interesting take on polls -- each response had [+] and [-] buttons next to it, and each poll could have 20 responses -- people would add responses 'til it filled up, and if a response was voted to -20, it was deleted, and someone could add a new response.
Not sure why it took off on Slashdot (meme?), but I think it became the "Other" or "None of the Above" type options, and then expanded into other sillier choices. And thus we get this poll. I can't believe he's winning over paco though. How depressing!
Yeah, Paco and Cowboy Neal are two of them. Since Cowboy Neal's home node has been around since 1999, it appears this gag has been here for a while. Watch the upper right corner of the Perlmonks pages. The next time you see the guy with a bird on his hat, do a mouseover.
Of course, unless you're one of the Illuminati you'll never fully understand, so just go along wth it.