The Disastrous Windows 95 Was Introduced to the World by Jay Leno

Those of you old enough to remember landlines and the financial dependability of Pauly Shore’s film career will likely recall Windows 95, the controversial operating system that, on the one hand, was a landmark moment in the history personal computing. But on the other, it seemed to crash with more regularity than Harrison Ford’s vintage plane collection.

Less well-remembered is the celebrity who helped Bill Gates introduce Windows 95 to the world: Jay Leno.

Yup, the Tonight Show host introduced the live, 90-minute launch event, as documented in an old recording that was thought to be lost to time before surfacing on YouTube in 2022.

Sure, Leno was a huge star at the time, but in many ways, he was an extremely odd choice for the gig. It’s not like he ever seemed especially computer savvy. Had he been tapped to introduce a classic car or a denim-only men’s fashion line, that would make sense. But America was asked to accept Leno’s word that the new OS was an “incredible product.”

Leno did joke about the fact that he was “not really computer literate” telling the audience of 500 members of the Microsoft development team that it took him two hours just to figure out how to use the clapper.

Leno’s monologue was predictably tacky. He immediately dropped an O.J. Simpson joke, bragging that Windows 95 is so powerful “it is able to keep track of all of O.J.’s alibis at once. Pretty amazing stuff.”

He also tried out some slightly more cutting material, joking about the “silly little mix-up” with the Justice Department, a reference to the government’s antitrust investigation into Microsoft that very nearly blocked the release of Windows 95.  

Leno then brought out Bill Gates, and the Microsoft CEO enlisted Leno to help him with a demonstration of the product while unloading the painfully sweaty zinger: “Windows 95 is so easy, even a talk show host can figure it out.” It has the vibe of one those ‘90s late-night infomercials.

Things didn’t get any better from there. Leno joked that the mouse can double as a castanet for when “I have Spanish friends over,” tried and failed to play a video game, performed a digital version of his “Headlines” segment, drove a computer mouse-shaped car and suggested that two audience volunteers should get naked. 

Leno’s relentless, blatantly insincere testimonials hyping the magnificence of Windows 95 perfectly illustrate why it’s so hard to like him. Sure, other late-night talk show hosts like David Letterman and Conan O’Brien have taken big paychecks to appear in commercials, but Leno was willing to thoroughly debase himself for a full 90 minutes, ditching his day job at a respected comedy institution to act as a perspiring pitchman for an ethically-dubious tech company.

The whole thing culminated with Gates blasting the Rolling Stones’ “Start Me Up,” a track that reportedly cost the company a whopping $3 million. It’s unclear how much Leno was paid. Hopefully enough to buy himself a new tie. 

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