Why did the Windows 95 CD have a Weezer music video on it?

Windows 95 just turned 31 years old and we’re revisiting that iconic operating system with a question: Ever wondered why the Windows 95 installation CD also contained a Weezer music video, a trailer for the Rob Roy film, and cartoons by Bill Plympton? You know, stuff that has absolutely nothing to do with the Windows operating system?

According to Raymond Chen, a long-time Windows developer at Microsoft, “Because it was fun!” Back in January 2006, the Windows veteran wrote in a blog post:

Why did the Windows 95 CD have extra fun stuff, like the “Good Times” and “Buddy Holly” music videos, the Rob Roy trailer, and the cartoons by Bill Plympton? Because it was fun! Why does one have to justify having fun? In addition to the multimedia fun, there was also video game fun, with the addition of Pinball and the mercifully-forgotten hovercraft game Hover! (Some of us thought it was so awful, we secretly called it Hoover!)

More recently, in February 2026, Raymond Chen wrote another blog post that answers how Microsoft got permission to include the Weezer music video on the Windows 95 installation CD.

Regarding the music itself:

First, Microsoft had to secure the rights to the song itself, which was negotiated directly with Weezer’s publisher Geffen Records, and apparently without the knowledge of the band members themselves. They were reportedly upset that they weren’t consulted but later realized that it was “one of the greatest things that could have happened to us. Can you imagine that happening today? It’s like, there’s one video on YouTube, and it’s your video.”

And then regarding the music video:

The video takes place in a reconstruction of a location from the Happy Days television program, and clips from that show were spliced into the music video to create the illusion that many of the characters from the show were part of the video. The lawyer responsible for securing the rights to the video had to contact all of the actors from Happy Days to get their permission. That lawyer thoroughly enjoyed the assignment. I don’t know whether he got to talk to the actors directly, or only to their agents, but I can imagine it being an interesting experience trying to find Henry Winkler’s telephone number (or his agent’s telephone number) with a chance of talking to The Fonz himself.

For more Windows memories, check out our visual walk down Windows history’s memory lane and our revisiting of the most pivotal events in Windows history.