When you think of a company full of men in suits and ties in the 90s, IBM was the first thing that came to mind. It was one of those companies whose offices had to be full of cubicles where alienated workers did their jobs, where the break room had a coffee machine instead of an air hockey table. You may have no idea what the offices looked like, but that was the image they and their products conveyed.

And something similar happened at Microsoft, which has a reputation—and rightfully so—for killing off competition based on its checkbook, adding more and more talent (and intellectual property) to its coffers, and being led by a computer geek with an incredible technological mind and a ruthless business shark: Bill Gates.

But at some point, that changed. Microsoft changed its image, and the best they could come up with was getting Bill Gates and the energetic Steve Ballmer to do all sorts of crazy things, one of which, 26 years later, is still one of the best videos on the internet.

Bill Gates and DOOM

First of all, in the 80s and 90s, almost all computer companies were very, very similar. IBM and Microsoft may have exuded an air of extreme corporate corporatism, but from Nintendo’s early Mario and Zelda development videos, we can see that they weren’t much different from other software companies. One made video games, the other made operating systems and other programs.

Come on, the workplace wasn’t an amusement park, but the commercials… oh, the commercials were something else. And thank goodness.

The video above you is a real gem. No, Windows 1.0 isn’t the point, what’s important is seeing a very young Steve Ballmer, 30 years old (yes, 30 years old), selling the operating system like it’s a telemarketing commercial. “Order today except Nebraska” is still one of my favorite phrases.

But rather than the announcement being weird (can you imagine Steve Jobs doing this?), it’s that there’s a sense of humor within the company. This video was used internally and it’s great, but maybe the turning point was seeing Bill Gates in DOOM.

The id Software game, directed by John Romero and Carmack, was revolutionary. Not only did it create the first-person shooter genre (although there were earlier games like Wolfenstein 3D), it also created an ecosystem where people could play multiplayer, and in addition, the game reached a multitude of platforms.

Here we’ve already moved on to Windows 95, so we’ve taken a major step towards announcing Windows 1.0, and we have Bill Gates coming into DOOM to announce DirectX internally.

This video is legendary because there are three things that need to be emphasized: It’s extremely tacky, Bill Gates is behaving very badly, and his finger is not even remotely close to the trigger at the moment of the shot. But… what difference does it make? Unfortunately, the video was never broadcast on TV because it was a comedy special for the Windows 95 launch event.

Gates still talks about the benefits of Windows 95 and the new game API (and does so rather boringly), but from a distance it’s gorgeous. And it’s best to say nothing about the outfit.

Baby don’t hurt me, don’t hurt me, no more

But let’s get to what we came for: see Gates and Ballmer dance. With Windows 95, we could already see the couple attempt a few steps in one of the funniest moments on stage. Imagine Microsoft staff stepping into the spotlight to the beat of the Rolling Stones’ ‘Start Me Up’ and moving their arms asynchronously as one another jumps around, as many of us do at a wedding.

Stop imagining and look at this:

This moment has been mistakenly classified as part of the Windows 95 presentation, but this is not the case. The presentation of the system is an incredible ‘plate’ but in a style that is much more entertaining than we could have imagined:

Raymond Chen wrote at Microsoft a few years ago that the video of Ballmer and Gates dancing awkwardly on stage must have been from a private event or sales event, but it wasn’t a public presentation or launch event.

But the pair reached the height of comedy a few years later with another internal video. For Windows 98, they both recorded a parody of the movie ‘A Night at the Roxbury’, where we can see them jamming to the beat of ‘What is Love’. ‘Getting into the rhythm’ means a lot, as a lack of coordination is evident at a certain point in the video.

But there’s something… weird. I mean everything’s weird in this video but at one point Bill puts on a record and the Trio’s song ‘Da Da Da ich lieb dich nicht du liebst mich nicht aha aha aha’ starts playing. It’s a song from 1982 that became legendary thanks to a great WV commercial in 1998.

So why are Ballmer and Gates yelling “DON’T TALK” after performing a great song? It’s because Microsoft’s competitor Sun Microsystems had made an announcement around the same time that they were messing with Microsoft about Solaris 7.

This was a parody of the WV commercial and also the 1997 Internet Explorer commercial in which Ballmer and Gates had already parodied the VW commercial.

Of course, this little disagreement between Sun and Microsoft resulted in the unforgettable ‘What is Love’ announcement.

There was more, there was more

In addition to the height of comedy, that parody commercial cosmos that slightly confused the competition was the genius of 1998, but Bill and Steve’s adventures did not end there. The duo continued to star in memorable moments in both Windows presentations and the first Xbox presentations.

Bill’s farewell video from Microsoft is great, but if we had to point out one more video where the duo showed off their great sense of humor, it’s this video from Developers Conference 2001 that… doesn’t go to waste. Even if it’s just seeing the two billionaire businessmen doing routines in their knitted sweaters while driving around town referencing ‘Scary Movie.’

After all, Microsoft was great, very cool. That seriousness completely disappeared when advertisers started designing scenarios where Bill Gates and Steve Ballmer would make the scenarios ridiculous and absurd, with Ballmer’s energetic personality and how bad (but bad, bad) Bill Gates would behave. I will definitely never see it again.

I can’t imagine Satya Nadella, for example, doing any of these things, and the closest (though not remotely) to that would be Tim Cook from the M1 iPad announcement. As they say now, 90s advertising was definitely a thing.

On Xataka | Steve Jobs had a talent that Bill Gates always envied: Always being Steve Jobs