It'll take me a bit to find/list all the silly songs I like, but it has to be done. 83

There's "You Are A Pirate" by Lazytown, "A Pirate I was Meant To Be" from Monkey Island, "The Sailor Song" by Toybox, "The D&D Song" (one of my personal favorites :D) by Stephen Lynch, "Shiny Teeth", though I'm not sure who made that one, the ever popular "Still Alive" song from Portal, and -of course- the Candy Mountain Candy Cave song from Charlie the unicorn. :3

....I know a song that gets on everybody's nerves, everybody's nerves, yes on everybody's nerves. I know a song that gets on everybody's nerves, and this is how it goes~

*flees before she gets murdered* XD