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The one where Friends did an hour-long video promoting Windows 95

Matthew Perry and Jennifer Aniston in 1995, shortly before their greatest triumph as actors.
Matthew Perry and Jennifer Aniston in 1995, shortly before their greatest triumph as actors.
Ron Galella/Getty Images

Today Windows 95 turns 20. And when it came out, it tried to be the vanguard since, for technology companies, the dream is a product so compelling, so sexy, and so fresh that it sells itself. Failing that, you can always hire a celebrity.

Celebrities hawking tech stuff is basically like spraying a mainframe with glitter. And the truly profound ones feature awkward, yet endearing, pitches for products that are both dull and obsolete. They'll be there for you when the rain starts to pour.

Matthew Perry and Jennifer Aniston try out Windows 95

Want to learn how to use the new Windows 95 system? Microsoft made a "cyber sitcom" to promote it.

It starred Matthew Perry and Jennifer Aniston in their Friends prime, playing themselves in a metafictional take where they sought a role in ... a guide to Windows 95.

The final product debuted on VHS on August 1, 1995, satisfying everybody who wished Friends were an hour long, had four fewer friends, and involved a guide to file management.

But this isn't the only example of cringe-inducing celebrity tech endorsements:

Ella Fitzgerald and Chuck Mangione sell Memorex

In 1979 came a fantastic celebrity duo: jazz musicians Chuck Mangione and Ella Fitzgerald, comically enthusiastic about the audio abilities of Memorex tapes.

The commercial relied on the catchphrase "Is it live or is it Memorex?" and, in doing so, made it look like Ella couldn't tell the difference between a live performance and tape.

Ray Charles loves the amazing Pioneer laser disc

In 1984, Ray Charles endorsed the laser disc player: "It's a video turntable that works with a laser beam, and that laser beam makes all the difference — they tell me." Charles appeared in a print ad, as well, with the quote, "Most video systems treat you as if you were deaf." (Charles himself had been blind since he was a child.)

The laser disc wasn't brand new at the time, but it did require some explanation (at best, the niche video player ended up in about 2 percent of United States households).

Johnny Cash hawks Johnny Cash Money Machines

In 1985, Johnny Cash needed cash, so he endorsed Canada Trust's new ATMs, which were actually called Johnny Cash Money Machines. Convenient banking apparently seemed like the perfect opportunity to use Cash's hard-living persona.

According to songwriter Mike McCurlie, Johnny acted about as you'd expect: he showed up to Toronto in a limousine, walked into the studio by himself, and said, "Hi, I'm Johnny Cash." McCurlie writes that Cash recorded the entire ad during a single long day before he flew back to Nashville.

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