5 Hilarious Times Comedians Could Not Understand Technology

Jay Leno launches Windows 95

Microsoft was justly proud of Windows 95, the first easy-to-use interface for average PC users. To celebrate, the company hired The Tonight Show's Jay Leno to host a launch party just for internal employees. Woo!

Khaki-clad Leno delivers a flurry of mid-90s jokes, most of which have lost their punchlines to history. Here are some samples, with translations for Jay's dated topical references:

“To give you an idea how powerful Windows 95 is, it is able to keep track of all O.J.’s alibis at once!” (Football star O.J. Simpson was on trial for murdering his wife.)

About an old computer? “This thing has a worse memory than Rosa Lopez!” (Lopez was a maid who gave inconsistent testimony at O.J.’s trial.)

“Everyone thinks Bill Gates is a genius, but I went into his den and his VCR was still flashing 12.” (No one knew how to set the clocks on 1995 videotape machines.)

Oy.  The crowd eats up Leno’s hammy shtick, likely thrilled that they don’t have to listen to Bill Gates do software demos for 90 minutes.

Jon Lovitz figures out MySpace

Younger comics like Dane Cook leveraged MySpace into thousands of tech-savvy fans back in the 2000s. Older comedians wanted in, but weren’t quite sure how to work the damn Internetz machine. Lovitz stares down his old-school webcam, doing facial warm-up exercises for more than 30 seconds before he finally asks: 

“Is it on?”

Steve Martin live-tweets his Windows 10 upgrade

In 2015, Martin took to Twitter for a blow-by-blow update of his computer’s attempts to upgrade to Windows 10.  The tweets are deleted now but lucky for us, GeekWire saved a bunch:

Staring at my Windows computer: "C'mon baby, update!"

— Steve Martin (@SteveMartinToGo) July 29, 2015

53%!

— Steve Martin (@SteveMartinToGo) July 29, 2015

127%!

— Steve Martin (@SteveMartinToGo) July 29, 2015

263% and my printer is smoking!

— Steve Martin (@SteveMartinToGo) July 29, 2015

Green ooze now coming out of my USB ports.

— Steve Martin (@SteveMartinToGo) July 29, 2015

OMG, A Bill Gates hologram is now standing in my office, saying, "Have you been good?"

— Steve Martin (@SteveMartinToGo) July 29, 2015

David Letterman slaps an iPad

Prior to the device’s release to the general public, Apple sent promotional iPads to lucky late-night hosts like Letterman. It didn’t take Dave long to screw up his, trying to demonstrate how the screen rotates before accidentally hitting the lock button and turning it off altogether.

Letterman then slaps the iPad, bangs it on his desk, and even licks it in an attempt to turn the damn thing back on. “The radiation this thing gives off is incredible," he offers by way of explanation. "You're supposed to wear a lead apron when you operate it."

Friends Jennifer Aniston and Matthew Perry learn how to use a computer

We’re back to Windows 95, now enlisting the white-hot Friends cast, or at least two of them, to explain the basics. If you ever wanted to watch Matthew Perry install a new printer, this is the video for you.

The Friends bring their trademark snark to the task of explaining simple computer functions, but somehow Aniston ends up as the butt of the jokes. “Taskbar?” she asks. “Is that anything like a Snickers bar?” What an idiot! She calls floppy disks “flappies” and even gets called out by a kid gamer for being a girl. 

Could this video be any more 1995? 

For more ComedyNerd, be sure to check out:

Tina Fey: 15 Now-You-Know Facts

15 More Jokes For The Hall Of Fame

Bill Maher: A History Of Being Terrible

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Top image: Microsoft