Answer: Weezer

Microsoft spared no expense when it came to promoting Windows 95. A not insignificant part of their marketing budget included commercials featuring music by the Rolling Stones as well as packing the actual installation CD with a “Fun Stuff” directory that included a video game (Hover!) as well as music videos, one of them being the song “Buddy Holly” by Weezer.

The music video featured members of the band dressed up like kids in the 1950s playing their set superimposed over footage from the 1970s-era nostalgia-driven sitcom Happy Days. The catchy tune combined with the spliced footage and a cameo appearance by popular Happy Days cast member Al Molinaro made the entire affair a memorable and kitschy video that new Windows 95 owners replayed by the millions.

The inclusion of the videos on the installation disc not only gave Windows users something to do with the disc and a reason to play with CD-ROM drives, but it pushed Weezer into the limelight; the surge in popularity and interest not only boosted sales for the band, but netted them four MTV Music Video Awards at the 1995 awards ceremony.