installation CD Archives

Winsage

August 25, 2026

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

Windows 95 included an installation CD featuring music videos such as Weezer’s “Buddy Holly” and “Good Times,” a cinematic trailer for Rob Roy, and animations by Bill Plympton. It also offered interactive content like the game Pinball and the hovercraft game Hover!. In February 2026, Raymond Chen wrote a blog post discussing the inclusion of the Weezer music video in the installation package, reflecting on the innovative efforts of Microsoft during that time.

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.

Winsage

April 9, 2025

Microsoft’s worst software flop was secretly packed with Windows for years

Microsoft Bob, launched in 1995 as a user interface to simplify computer navigation, sold only around 30,000 copies before being discontinued. In 2001, during the development of Windows XP, Microsoft included an encrypted version of Bob on the installation CDs to fill 30 MB of unused space and deter piracy. This decision was made to slow down users with dial-up connections attempting to illegally copy the operating system. The developer found floppy disk images of Microsoft Bob, encrypted them, and added them to the Windows XP CD, meaning that purchasers of Windows XP received a copy of this previously unsuccessful software.