I want to thank whatever stars aligned that surfaced this video of the Windows 95 launch event in my algorithm. While clips from the presentation have floated around online for decades, the full 90-minute keynote has been harder to track down. Uploaded this week by the angels over at the Blue OS Museum YouTube account, the complete presentation is an absolute time capsule of technology culture as it existed on Aug. 24, 1995. It also features some incredibly cringe moments, most of which stem from Jay Leno’s cheesy and problematic joke-telling.
My face felt flush the entire time I watched this presentation from all the nostalgia pulsating throughout it. There are all the requisite hairstyles, khaki pants, and overly-used Bill Clinton jokes that make this a quintessential event of the ‘90s. Here are some of the best and worst parts of Microsoft’s Windows 95 launch event.
A warning that if you do watch the presentation in its entirety, you will have The Rolling Stones’ “Start Me Up” stuck in your head for the rest of the day.
The ‘90s nostalgia is in full force from the very beginning. From the ska-funk intro to the warning prompt that pops ups over a visual of clouds wading in the distance to the oversized clothing worn by nearly every person to the excessive use of canted angles to the graphics and fonts randomly stretching in every direction, the entire video feels like a being transported back to a moment in time we’ll never be able to recreate.
One particularly lovely bit about watching the Windows 95 keynote is that it was also a look at developer life and culture back in the ‘90s. Most of the young devs that are featured throughout are wearing casual clothing rather than the paper bag khakis that identified a CEO. There’s more of an air of authenticity to the event (nerds nerding out over nerd stuff). Compare this to modern times when keynotes often feel stiff and feature polished executives from central casting.
Joe Belfiore’s dating video
The Windows 95 keynote starts with candid, Real World-style confessionals from Microsoft employees and developers about their time working on the operating system. There are jokes about junk food, general hygiene, and even anecdotes about an employee who kept working despite a broken limb.
Then, it randomly pivots to now-Corporate Vice President Joe Belfiore mentioning that he hasn’t been dating much. He’s the only one they ask this question, which makes me ask: was Belfiore the Zaddy of Microsoft in the ‘90s?
Steve Ballmer Yells
Afterward, we pivot to this segment with Steve Ballmer yelling at you about Windows 1.0 and all it can do. Ballmer is pretending to be a salesperson in the ‘80s, shilling the wonders of Reversi on a home PC. He’s screaming the entire time. It gave me a headache.
The Unbearable Persistence of Flash Photography
Adding to my headache was the very overt use of flash by the photographers at the event. But I can’t blame them because they probably used film cameras and needed the extra light to capture the moment. I am so thankful that we have cameras with giant sensors now and can kiss the constant strobing of lights goodbye. It would make my job covering press events so much harder.
It’s All Fun and Games Until the FTC Comes Knocking
Of course, there was an antitrust joke. If you were just a baby zoomer back then, Microsoft was embroiled in a battle with the Department of Justice over its antitrust practices. The DOJ was afraid Microsoft would use its position to gain a monopoly over the browser market with its pre-packaged Internet Explorer app.
The joke comes off as Microsoft attempting to publically thumb its nose at the investigation. But the FTC had the last laugh after a years-long legal battle ended with a bruised Microsoft agreeing to a settlement and narrowly avoiding being broken up into two companies.
All operating systems have their share of fans, and they were certainly in attendance at the Windows 95 event. About twenty minutes into the presentation, Leno and Gates call up folks from the crowd onstage to try out Windows 95’s new migration tools (cool!). Up comes a woman to the stage with a giant Windows icon emblazoned on the front of her shirt, followed by Pete wearing an impressively constructed CD-ROM vest.
The Microsoft Mouse Car
It took me a second to figure out that this little electrical vehicle was supposed to represent the original Microsoft rollerball mouse. I was too busy parsing the way Leno introduced the segment. “By the year 2000, Al Gore will have us all driving one of these,” he jested. So glad the idea of driving an electric car in the ‘90s got an easy laugh. Everything’s worked out great since then.
Leno Harasses a Random Woman
Microsoft had a few women in this Windows 95 presentation, but they were a punchline from the beginning. The second of four women to be prominently featured is on for a few seconds and says nothing about the new operating system. Instead, she’s harassed by Leno, who asks her how she’s doing and then follows up with, “Can I show you my mouse sometime?” It doesn’t even make sense as a disgusting euphemism. But Leno accomplished what he wanted to do — demean a stranger and assert power.
Killing Has Never Been So Much Fun
Leno takes it over to share the great news of autoplay with a demo of Microsoft’s Fury 3 running off of a CD-ROM. “Computers are really a tool to search, destroy, and educate,” Leno comments. “I never thought killing could be so much fun.” A classic joke from a comedian who never killed in his life.
So Many O.J. Jokes
Timely jokes about one of the biggest murder cases of the decade don’t seem like the best way to sell an operating system to me, but I guess it worked like gangbusters back then.
Windows 95 Itself
Despite some of the more shudder-worthy moments of the keynote, we have to offer a little credit to Windows 95 for where we are now in computing. So much of what we consider a modern desktop experience was contained within this early version of Microsoft’s operating system. You can witness folks in the presentation laud some of the most simplistic computer abilities we take for granted in this day and age. The internet was slow as hell, you used to have to physically tether computers to transfer files, and running more than four applications crashed your system. Well, I guess that last one is still true today if one of the applications is Chrome.
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