The Sidekick Was the Best Smartphone Ever

Phones have become boring slabs of glass. The Sidekick pointed another way.

Clive Thompson
Debugger
Published in
6 min readApr 14, 2022

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Last weekend, I cleaned out one of my Messed Up Old Tech drawers, with help from my 14 year old son. We tossed out some ancient Mesopotamian Zip drives, a copy of Microsoft Office 2000, and a tangle of cords whose original functions are lost to the mists of time.

At the bottom of the drawer we found a real prize, though:

My 2004 Sidekick II phone.

If you were in your teens or twenties back around the turn of the century, you probably remember this device. The first version arrived in 2002; the second (the one you see above) in 2004.

Back in the early ‘00s, mobile phones were still awfully basic — they made phone calls and sent texts. To compose a text, you pecked away on the twelve-button keypad. That was it, mostly.

So the Sidekick arrived like a pure blast from the future. It had a complete web browser, built-in messaging apps (like AOL Instant Messenger)…

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Debugger
Debugger

Published in Debugger

Debugger is a former publication from Medium about consumer technology and gadgets. Currently inactive and not taking submissions.

Clive Thompson
Clive Thompson

Written by Clive Thompson

I write 2X a week on tech, science, culture — and how those collide. Writer at NYT mag/Wired; author, “Coders”. @clive@saturation.social clive@clivethompson.net