Didn't that start with Disney?

The DMCA was 1998. Wasn't that around the same time that Microsoft was getting hammered by the DOJ?

My impression is that the general consensus has that being about the time that Microsoft learned its lesson about ignoring lobbying. Maybe Oracle had something to do with it, but it seems like Microsoft probably missed that particular ship.

There were criminal penalties for willful, for-profit performances of dramatic and music works in 1897 US copyright law. The 1909 act expanded this to all types of willful, for-profit infringement. I'm reasonably sure neither Microsoft nor Oracle had anything to do with this.