Microsoft put Weezer’s Buddy Holly on Windows 95 just for "fun" — but only after a legal battle no one talks about

In his ongoing Old New Thing series, Microsoft veteran software engineer Raymond Chen shared an intriguing story about why the Windows 95 CD included a wide range of multimedia extras. But also how the company managed to pull it off despite copyright hurdles that could have derailed the plan.

Back in the day, before Microsoft got obsessed with AI and started integrating the technology across its entire tech stack, Windows was seemingly cooler. However, the company is seemingly retracing its steps by listening to feedback from users with the aim of making Windows 11 better.

Windows 95 shipped with more than just software in the CD; it also included fun stuff like the Good Times and Buddy Holly music videos, the Rob Roy trailer, and the cartoons by Bill Plympton.

Chen revealed that Microsoft included the extras just for the fun of it while simultaneously strategically showing off the operating system's multimedia capabilities.

The engineer revealed that adding multimedia extras to Windows 95 was no easy feat. Microsoft had to secure rights to the Buddy Holly song, negotiating directly through its legal team with Weezer’s publisher, Geffen Records.

However, Microsoft was in the middle of discussions with the recording studio without the band's knowledge. As expected, this sparked a bit of pushback from the band, but they 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.”

Weezer - Buddy Holly (Official Music Video) - YouTube

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The negotiations were exclusively for the audio, and now that Microsoft had secured the rights to use it, the company now needed to shift its focus to visuals.

It's worth noting that the video took place in a recreation of the Happy Days television show, which was set in the late 1950s and early 1960s and broadcast during the 1970s and 1980s.

This placed the software giant in a pickle. "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," Chen indicated. "The lawyer responsible for securing the rights to the video had to contact all of the actors from Happy Days to get their permission."

Microsoft was forced to ask for permission from the actors to be featured, including , most notably, Henry Winkler of Arthur 'The Fonz' Fonzarelli fame. But as Chen frames it, "that lawyer thoroughly enjoyed the assignment".

What’s the most memorable Windows 95 extra for you? Let me know in the comments.

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