Matthew Perry and Jennifer Aniston Star in 1995 Windows 95 Instructional Video

In 1995, during the height of their fame on the TV show Friends, Matthew Perry and Jennifer Aniston appeared in a unique promotional video for Microsoft titled the ‘Windows 95 Video Guide.’ Marketed as the ‘world’s first cyber sitcom,’ the 60-minute VHS production aimed to teach users the essentials of the new Windows 95 operating system. In the video, Perry and Aniston play themselves, visiting Bill Gates’ office to audition for a Microsoft video guide. They are introduced to the top 25 features of Windows 95, including the Start menu, right-click functions, multitasking, and the Recycle Bin, all explained through interactions with quirky characters such as a martial arts guru and ‘Joystick Johnny.’ The video also captures cultural moments of the mid-1990s, like Aniston calling copy-pasting ‘trippy’ and Perry figuring out how to email a friend in a grunge band. The VHS is organized into three sections: the cyber sitcom, a detailed technical walkthrough, and answers to 20 frequently asked questions. This production provides a fascinating glimpse into the early efforts of tech marketing and education, highlighting how Windows 95 helped bring personal computers into the mainstream and bridged entertainment with technology education.