Windows 95 is 29 years old today, released on August 24th, 1995. I still look back fondly on those days, especially playing DOS games on it.
The launch of Windows 95 on August 24th, 1995, was one of the most highly anticipated moments in tech history. The excitement surrounding the release was amplified by a memorable launch event, where comedian Jay Leno joined Microsoft co-founder Bill Gates on stage, cracking jokes alongside the entire Windows 95 development team.
The journey to Windows 95 began much earlier, around March 1992, just before Windows 3.1 hit the market. At that time, Microsoft was busy developing Windows for Workgroups 3.11 and Windows NT 3.1, with their sights set on a visionary project called Cairo. Cairo was supposed to be Microsoft’s next-generation operating system, built on the foundation of Windows NT, with a revolutionary user interface and an innovative object-based file system. While Cairo was expected to debut in 1994, parts of it were eventually released in July 1996 as Windows NT 4.0, albeit without the much-anticipated object-based file system, which would later evolve into what we know as WinFS.
The release of Windows 95 was marked by a massive marketing campaign, featuring the Rolling Stones’ hit “Start Me Up” in TV commercials that highlighted the new Start button, a feature that continues to be a staple in modern Windows versions. Microsoft also produced an hour-long cyber sitcom starring Jennifer Aniston and Matthew Perry to promote the software, which quickly became a sensation. Within the first five weeks, a staggering 7 million copies of Windows 95 were sold.
While the mainstream audience celebrated the launch with fanfare, tech enthusiasts were busy debating the merits of Pentium versus 486 processors, choosing between IDE or SCSI hard drives, and deciding whether to go for double-speed CD-ROMs and Sound Blaster audio cards to get the most out of Windows 95. The operating system introduced several significant features, but the most notable were the new Start button, menu, and taskbar, which made it easier to find applications and navigate the system. These improvements in multitasking and the graphical interface were a significant step up from the older Windows 3.1 and MS-DOS days, although users of Macintosh and OS/2 at the time found the interface somewhat familiar.
But Windows 95 wasn’t just about the Start button. One of the key advancements was its support for long filenames, up to 250 characters—a simple feature by today’s standards, but revolutionary at the time. Another major introduction was Plug and Play, designed to automatically detect and install hardware. However, the early implementation of Plug and Play was notorious for its unreliability, earning it the nickname “Plug and Pray” due to frequent device installation issues and IRQ conflicts.
Beyond the operating system itself, Microsoft had ambitious plans for expanding the Windows 95 ecosystem. The software came bundled with the Microsoft Network (MSN), an early attempt to provide internet access via email, chat rooms, newsgroups, and the first WWW homepages, all through a dial-up connection. While MSN charged a monthly fee and extra for usage beyond three hours a month, it laid the groundwork for Microsoft’s future internet ventures. Today, MSN lives on as a web service accessible through various apps and browsers.
Windows 95 also introduced features aimed at improving the user experience across multiple devices. My Briefcase was an early tool for syncing files between a laptop and desktop, a concept that has evolved into the cloud-powered OneDrive service we use today. The operating system also supported user profiles, allowing different family members to have their own personalized desktops and settings.
For those who wanted even more from Windows 95, Microsoft offered the Microsoft Plus! pack, which included the Internet Jumpstart Kit (an early version of Internet Explorer), theme support, and various system utilities. As Windows 95 evolved, updates introduced new features that paved the way for Windows 98, which would arrive three years later with even more enhancements.
Looking back, Windows 95 was a landmark moment in computing history. From its revolutionary features to the iconic marketing campaigns, it left an indelible mark on the tech world. Whether it’s Bill Gates and Steve Ballmer’s legendary “Start Me Up” dance or the midnight lines for CD-ROM copies, Windows 95 remains a classic, just like the era it defined.”
