5 Apple’s Newton MessagePad 2100 ($1,000)
There’s been a lot of talk about “thousand-dollar” smartphones in the news lately, which brings me back to a time in 1997 when Apple had just introduced an updated version of its Newton PDA — the Newton MessagePad 2100, which chiefly boasted improvements in speed, latency, handwriting recognition, and display contrast over its predecessor. Wouldn’t you know it, though? The Cupertino-company still thought that even with these minimal improvements it could sell its wannabe, grayscale Palm Pilot for a cool $1,000.
The thing is, Apple didn’t really start turning things around until a little while after the introduction of the iMac G3, iPod, and other key products years later. So while the company may have thought it had something really neat and innovative on its hands, the reality is, even in 1997 for just $300, you could’ve bought a Palm Pilot device that was just as capable. Some may disagree, but the bottom line is the Newton 2100’s improved capabilities certainly didn’t warrant a $700 premium.