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Microsoft put Weezer’s Buddy Holly on Windows 95 just for "fun" — but only after a legal battle no one talks about
Winsage
February 15, 2026

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

Raymond Chen, a software engineer at Microsoft, shared a narrative about the multimedia content on the Windows 95 CD, highlighting the creative vision and copyright negotiations involved. Microsoft initially secured rights for audio content but faced challenges with visual media, particularly a recreation of the TV show Happy Days. This required obtaining consent from original cast members, including Henry Winkler. The legal team, tasked with this, enjoyed the process of navigating permissions.
How Microsoft's legal eagles wrangled Happy Days for Windows 95
Winsage
February 11, 2026

How Microsoft’s legal eagles wrangled Happy Days for Windows 95

Microsoft's legal team was responsible for securing permissions from the cast of the television series Happy Days to feature a Weezer music video on the installation CD of Windows 95. The music video, "Buddy Holly," was included to showcase the multimedia capabilities of the new operating system, which supported 32-bit processing and video playback. Microsoft negotiated rights with Geffen Records, and the band members were initially unaware of the arrangement. Despite concerns about their music being associated with software, the band later recognized the promotional benefits from Windows 95's sales. Additionally, obtaining video permissions from the actors in Happy Days posed a challenge for Microsoft's legal team.
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