---
title: "Boomer cringe: Windows 95 keynote /w Bill Gates & Jay Leno"
post_id: 13850
url: "https://lui.vn/boomer-cringe-windows-95-keynote-w-bill-gates-jay-leno/"
language: "en"
type: "article"
published: "2022-05-19T11:24:19+00:00"
modified: "2026-07-03T10:54:21+00:00"
categories: ["Nerdom & Games"]
kicker: "Boomer Cringe Deluxe"
intro: "Windows 95 keynote with Bill Gates and Jay Leno. Forget Steve Jobs - Microsoft knew how to put on a show. Peak 90s energy."
image: "https://lui.vn/wp-content/uploads/2022/05/windows-95-boot-screen.png"
image_credits: "Image: Windows 95 bootsplash by Microsoft"
---

# Boomer cringe: Windows 95 keynote /w Bill Gates & Jay Leno

Forget the lame [presentation of the first iPhone](https://www.youtube.com/watch?v=VQKMoT-6XSg) with Steve Jobs in 2007. It was predictable, boring, and uninspired. Microsoft and its former CEO Bill Gates, on the other hand, knew how to introduce a new product to the world: like Windows 1995 in, well, 1995. The ingredients: a small scene in a beer tent with ultra-nerdy Windows 95 fanboys, Bill Gates (the [richest person in the world in 1995](https://www.google.com/search?q=bill+gates+wealth+1995) with a net worth of 12.9 billion USD), and [Jay Leno](https://en.wikipedia.org/wiki/Jay_Leno), a famous American comedian at the time. The whole Windows 95 presentation is pure boomer cringe: stone age technology (IE 1!), nerds, politically and socially incorrect jokes, geeks, disturbing corporate propaganda, bad hairstyles, and tattered outfits.

Almost every part of the Windows 95 keynote that was broadcast around the world represents the zeitgeist of the mid-90s and would be unthinkable and impossible to do in that form today from a business perspective. No company would allow itself to be mocked on its own stage and have the show hijacked by lame jokes, and especially would not leave any part of a presentation to chance. It’s messy, weird, and unprofessional. And it’s for these reasons that the Windows 95 keynote has historical value – and is as funny as it is scary.

Boomer cringe at its finest.

## Microsoft Windows 95 Launch with Bill Gates & Jay Leno (1995)

[YouTube video](https://www.youtube.com/watch?v=_JzfROUDsK0)

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