I don't watch much Web video, in part because the SF office network is so slow that it's nearly impossible to watch video at the office. So for the upload-a-video challenge, not a lot of options spring to mind. It's either the overdone Kimmel/Affleck video, Japanese teenagers reenacting Live Aid, or Liam Finn on Letterman. The last was easiest to find.
And so, I give you... Liam Finn.
You really wanted the other one, though, huh. That's cool.