Release Date: 2009
Director: Akiva Schaffer
Fun Fact: The song was actually so well received it was nominated for a Grammy award!
I love The Lonely Island. They're so funny yet talented at the same time. Mocking hip hop videos is their forte yet they do it so well they've become a well established hip hop group in their own right.
The song and video basically mock a load of general hip hop videos, going on about how awesome they are and how cool they look. It's obviouslly usually on/in cars and stuff but this time they just "bang on" about how awesome it is that they're on a boat. It's an incredibly funny video that mocks hip hop, but it ends up being a very good track as well!
Note: This is the first and last video from the year 2009 in this list.
Here's the video for your enjoyment!