The one I remember most was the Barenaked Ladies doing a music video about racial harmony: The Ballad of Gordon.
This completely blew my mind when I realized it was them. I had that song stuck in my head years later.
"She might have 12 times the knowledge and experience of wrestling that I do, but this kid's probably never dropped out of high school & made her parents cry, probably never had to quit being an idol thanks to depression, probably never failed the job interview for an escort club. I got my own 12 years of experience."