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20 years ago today, Microsoft launched Windows 95, with help from the Rolling Stones “Start me Up.” The song choice was prophetic. For better or worse, the launch of Windows 95 was the beginning of a new era for Microsoft. The PC market had already been shifting towards IBM PC clones and Windows operating systems, but the launch of Windows 95 (codenamed Chicago) cemented Microsoft as the juggernaut of the PC industry. Apple’s market share had spiked in 1991 thanks to the introduction of low-cost Mac PCs, and the company launched its first PowerPC chip in 1994, but Windows 95 and its successors pushed Microsoft to an estimated OS and Office suite share of 95% or more. In honor of Windows 95’s 20th anniversary, we took a fresh look at an old frenemy.

Note: We’ve used the OSR2 version of Windows 95 for screenshotting because it plays nicer with modern VMs than the original flavor. The very first version of Windows 95 didn’t include a web browser, FAT32, DirectX, USB, IRQ steering, or fully support either Intel’s Pentium Pro processor or MMX extensions. Our comments on the OS do not rely on these features, except where indicated.

Startup and installation

Human memory is a funny thing. If you’d asked me yesterday, I could’ve told you that while Windows 95 billed itself as a 32-bit operating system, it was more of a 32-bit patch on top of a 16-bit core, hence the old joke that described it as “32 bit extensions and a graphical shell for a 16 bit patch to an 8 bit operating system originally coded for a 4 bit microprocessor, written by a 2 bit company, that can’t stand 1 bit of competition.” Like Windows 3.1, Windows 95 still leaned heavily on DOS, and anyone installing it on a new system had to be fairly familiar with the command line.

How familiar? Let’s just say I haven’t found myself partitioning a drive in FDisk for at least a decade.

After configuring my 6GB partition (Windows 95 OSR2 could address a drive up to 8GB, but I didn’t want to push my luck), I headed into the main setup program. The OS asks a number of low-level questions compared to modern setups, and I chuckled, remembering how shoe-horning the OS into older hardware often required the “Portable” or “Compact” options.

Modern day operating systems use a system called Plug-n-Play to determine which drivers you need. Windows 95 was meant to debut the feature, but the early versions were more aptly known as “Plug and Pray.” Then-new PCI cards theoretically supported the feature, but that depended on vendor driver support. Plenty of systems deploying Windows 95 still used hardware jumpers to configure one or more peripherals, which could play merry hell with the operating system’s fledgling attempts to automatically configure its own options. Setting up peripherals, particularly network cards, sometimes became a slow-rolling disaster of manually defining IRQs and interrupts in BIOS, in Windows, or attempting to coax the OS into configuring the whole thing automatically.

The splash screen was its own walk down memory lane.

Innovation (for good or ill)

Stepping back to Windows 95 is a surreal mix of familiar menus and a jarring lack of capabilities. Windows 95 popularized and standardized the use of right-click menus (two and three-button mice had existed for years, but right-click functionality was defined program-by-program). At first glance, Windows 7 and Windows 95 might seem to have nothing in common, but compare the “Advanced Display Properties” menu in W95 with the “Advanced Settings” menu of Windows 7’s display settings and the same menu in Windows 10.

Windows 95 DNA is still buried in Windows 10. Click to enlarge.

No, they aren’t identical — but you can clearly see bits of Windows 95’s DNA carried forward to Windows 10, which launched 20 years later.

Windows 95 debuted design elements that we’re still using, from the Start Menu and right-click to File Explorer and the Task Manager. That doesn’t mean all these features worked out of the gate, though. Plug-and-play hardware was a great idea, but it took years before the function actually worked. By default, Windows 95 OSR2 dumps you into the abyssal hell of “Active Desktop” by default. For those of you who don’t remember this particular feature, it ate system resources, pegged CPU cores, filled the desktop with a clutter of widgets, and introduced a number of security flaws. As an additional bonus, it also allowed HTML elements to be integrated into the Windows desktop.

IE 4.0 can still access Google

I decided to try accessing Google and the Internet, mostly on a lark. Hilariously, IE 4.0’s MSN redirect still accesses the page, but a browser this old can’t actually display anything. Google works, but a site like ExtremeTech throws a few hundred script errors, then shuts down. The OS may still work, but the browser is a lost cost.

What did people think of it?

People remember the launch of Windows 95 as a huge watershed moment for the PC industry, but there’s some evidence that this is hindsight talking rather than objective fact. While the OS sold well, its stability and capability were criticized by users and the press alike. The New York Times characterized it as “an edifice built of baling wire, chewing gum and prayer, but you will probably end up living there.”

A subsequent quote in the same article captured both the nascent promise and real-world problems of using the operating system: I opened the box, swapped video cards and rebooted. In the past, software hassles would have come next, but Windows 95 calmly identified the new card and installed the proper software driver. Too bad the driver had no idea how to change refresh rates to eliminate monitor flicker. The hassles, involving an AUTOEXEC.BAT file and DOS software that required a couple of on-line sessions to track down, were back.

For many people, Windows 95 was an additional layer of complexity running on top of already rickety software. The widespread security flaws that led Microsoft to postpone the OS that became Vista and double-down on improving Windows XP wouldn’t begin to crop up until the Windows 98 era — in Windows 95, the Internet is still so new that the operating system refers to an “Internet Mail” account rather than “email.”

If I had to guess, I’d wager that few people actually miss Windows 95. It was less a perfected form than an early glimpse of what Microsoft could deliver. Up until the advent of Windows 7, Windows 2000 or XP was generally viewed as the “best” version of the operating system, with Windows 7 having inherited that mantle in the recent past.

Even so, it’s interesting to look back at where things started. Windows 95 was buggy and rickety, even half-baked — but it set the stage for the next 20 years of Microsoft computing and OS evolution.