WTF Microsoft

Overview

The video is a comedic, commentary-style walkthrough of Microsoft’s oddball Windows-era marketing and internal videos—especially from the 1990s and early 2000s. It uses these materials to highlight how Microsoft culture blended tech promotion with pop-culture parody, and sometimes with controversial or dated humor.

Key Points and Analyses

“Why Nebraska? (Order today.)”

The video centers on a strange Windows ad line—“Except Nebraska”—and argues it isn’t a secret Windows metaphor. Instead, it frames the phrase as a Cold War-era telecom reality:

• Nebraska had unique telephone network/trunk constraints.
• Many ads/campaigns excluded Nebraska because of how calls were routed at the time.
• The wording is treated as both:
  • a mocking reference to the era’s fine-print state exclusions, and
  • a reflection of actual routing/technology limitations.

Microsoft’s 1990s ad style

The presenter claims Microsoft produced commercials that were often:

• visually uninspiring, and
• sometimes based on jokes about appearance/body types.

In this framing, the purpose of the ads is less about clear product messaging and more about quirky entertainment and satire.

The internal “sell Windows 386” cassette becomes an action parody

Microsoft reportedly sent internal cassette material to retailers to persuade them to buy Windows 386. The video describes it as:

• boring for roughly the first seven minutes, then
• abruptly shifting into an action/spy-mission parody (compared to Mission: Impossible).

The “mission” framing and dialogue are used to sell the idea that Windows can run multiple programs and help assemble work from scattered windows/files.

A long Windows 95 training/advertising video mocked for jokes

The video also describes a roughly 50-minute Windows 95 production featuring Matthew Perry and Jennifer Aniston, portrayed as a tutorial that includes:

• many terrible jokes, and
• confusing, poorly structured segments.

Overall, it emphasizes how Microsoft’s marketing/training materials could be more comedic than helpful.

A broader internal tradition (Gates/Ballmer era)

The video argues that under Bill Gates and Steve Ballmer, Microsoft employees created amateur “school-film” style parodies internally—sometimes:

• expensive in effort, and
• heavy on pop-culture references.

It suggests this culture occasionally foreshadowed what later appeared in public, including content that eventually leaked or spread.

Parody examples and pop-culture mimicry

The presenter compares internal sketches to mainstream media, claiming Microsoft tried to recreate recognizable formats—such as:

• The Roxbury-style comedy, and even
• The Matrix.

These comparisons are used to mock both Microsoft and the marketing habits of the era.

Windows XP campaign cancellation after 9/11

The video recounts an XP commercial where people appear to be “flying,” likened to the Windows XP screensaver. It claims:

• the ad was prepared in August 2001 for a November 2001 release, but
• it was effectively reworked/canceled due to 9/11, because flight imagery was deemed inappropriate.

It also claims remnants using Madonna’s “Ray of Light” could survive only if they didn’t depict flying, explaining why different XP ads differed.

Overall Conclusion

The presenter concludes that Ballmer’s leadership style and Microsoft’s internal creativity made the brand’s output feel unusually bold and meme-able. They express doubt that later leadership (e.g., Satya Nadella) would continue the same internal parody tradition.

Presenters / Contributors Mentioned

• Greta (narrator/presenter)
• Steve Ballmer
• Bill Gates
• Matthew Perry
• Jennifer Aniston
• Chris Kattan
• Will Ferrell
• Satya Nadella
• Madonna
• “Crazy Eddie” (referenced as a character/campaign; not a contributor to the video itself)