It might be news to many of today’s selfie-snapping, hashtag-happy millennials, but Windows 95 was a huge deal. I’ll never forget the day my dad came home from CompUSA with that blue, cloud-covered box and we cracked open the CD-ROM for the first time. The installation felt like it took took all night, but once the disc drive stopped whirring, we were in. This totally new interface–it introduced radical new concepts like the Windows “Start” menu and the taskbar–would be our gateway to so many new and wonderful computer things. It even came with a full-length AVI file of Weezer’s “Buddy Holly” music video, for some reason.
It’s hard to believe that Windows 95 shipped exactly 20 years ago today. And while few of us have machines that still run that wildly popular, PC boom-fueling operating system, we can still celebrate it birthday via YouTube. And as it turns out, there is no shortage of incredibly awkward videos out there to help us keep the memories alive.
Here are some of the best/worst Windows 95 videos in existence.
This extended, nearly 9-minute TV commercial for Windows 95 is totally insane. If it wasn’t so obviously made in 1995, you wouldn’t have a hard time convincing anyone it was actually a Tim and Eric sketch. In between over-the-top sight gags and dad jokes from commercial’s main star, we get exciting action shots of Microsoft Excel generating charts, and pixelated video games that were probably pretty neat at the time. The video also shows off notable features like a program that lets you look at maps on your computer and the ability to insert WordArt into your documents.
The mid-’90s PC boom had a big impact on the way people work. And while these new machines may have been exciting for curious kids and geeky enthusiasts, not every middle-aged office worker was thrilled about the prospect of learning a completely new way to get things done, especially before computing interfaces were as intuitive as they are today. But if you were a lonely dad in 1995 with a sudden need to learn Excel and Internet Explorer, you were in luck: Somebody made this amazingly awkward tutorial starring Greta, a bikini-clad ’90s babe. Greta walks the viewer through the features of Windows 95 and its key software, all while dropping vaguely sexual innuendos to keep the lessons, as she puts it, “as pleasurable as possible.” Before there were YouTubers, there was Greta.
With Windows 95, Microsoft introduced a feature that endures to this very day: The Start menu. To market this new innovation in desktop computing interface design, the company did not waste the obvious opportunity to license the song “Start Me Up” by the Rolling Stones, which appeared in early TV commercials for Windows 95. The song also plays throughout this promotional launch video, which features Bill Gates extolling the promise of new communication paradigms like “electronic mail” and runs through some exciting screen-by-screen B-roll footage of Windows 95 in action. The highlight of this video, however, is an onstage appearance by Jay Leno, who uses his classic, painfully unfunny comedic stylings to crack jokes about the computer mouse and quip that Gates is “so successful that Ross Perot is his chauffeur.” From start to finish, the whole thing is delightfully ’90s, and replete with pleated khakis.