Media: DVD
Who: written and directed by Eugene Jarecki,
When: 2005
What: An ambitious documentary that attempts to answer the question of why the US invaded Iraq in 2003. Within roughly 90 minutes, the film wrangles with broad issues such as the collusion between congress and the military/war industry, a history of American foreign policy and manipulation of media. Features interviews with prominent political and military figures.
Links: official site, Democracy Now! interview, Mises Institute review

Media: live music performance and lecture
Who: American band, Negativland
When: 2003
What: The questions being raised over YouTube reminded me of a presentation I saw of this band a few years back at Innis (U of T). Over the years, Negativland have generated an impressive output of experimental music and video. The band is particularly vocal about copyright issues, frequently uses samples and apparently have been sued many times. They also have a history of pulling pranks on the mainstream press/news media.
Links: official site