The Legend of Neil Returns
The Legend of Neil is over 10 years old (2008) and the creator, Sandeep Parikh bought back the rights to the show and is re-running it on his youtube channel. It remains awesome and harkens back to a time not so long ago when web content was in its infancy. Also it is interesting to see how quickly the memory of different experiences degrades. I remember almost nothing from Legend of Neil, so rewatching it 10 years later has been very fun, and I look forward to doing it again in 10 years.
A small bonus set of other early web content pioneers: The Guild, Collegehumor (still around – enjoyed this recent skit), RocketJump, Dr Horrible, Save the Supers.