How about Weezer's "Buddy Holly" music video on the Windows 95 CD? Sometimes when I see articles about viral videos and views I wonder where that video would rank if we had the capability to track its plays.
Recently I had a flashback to a similar video on one of the MSDN CDs called "Studs from Microsoft". Studs, for those who weren't in the USA at the time, was a sort of dating game show in which two improbably attractive men each dated the same three improbably attractive women. The men are then quizzed on what the women thought of their dates and of the men, with the potential grand prize being a dream date with your preferred girl of the three. But that wasn't the point, the real entertainment value was all the ribald sexual talk in the questions and answers.
Studs from Microsoft was a parody of this format, with the "studs" replaced by Microsoft programming nerds, from Seattle area sketch comedy show Almost Live!. It is also notable for featuring a pre-Science-Guy Bill Nye.
The entire album "Songs of Innocence" was forced onto everyone's iPhone, whether they wanted it or not. Apple thought they were doing everyone a favor. When some people deleted it from their iPhones, it came back on its own.
"You're going to listen to this U2 album, and you're going to like it!" -- Tim Apple