20th Anniversary Mac (1997)
On a superficial level this is actually a really well-thought out machine. The 20th Anniversary Mac (TAM) was one of the first Macs to be designed by Jony Ive, and it paved the way for the vertical design of computer that forms today's iMac. It wasn't a terrible machine in terms of specifications (although not amazing by any stretch) and it had a built-in TV and FM tuner.
The TAM was almost comically expensive, though. It cost $7,499 at launch, although it had specs similar to the PowerMac 6500 (which was $2,999). Apple killed it off within a year and Jony Ive moved on to the iMac.
Apple USB Mouse, AKA 'Hockey Puck' (1998)
The mouse is a pretty simple device; you use it to move the cursor around and click things. It's hard to get it wrong. But Apple achieved exactly that with this, the Apple USB Mouse (also known as the "Hockey Puck" mouse). The edition of the mouse released with the iMac was perfectly circular, which looks neat but makes it difficult to hold and orient correctly; which in turn makes it difficult to achieve pixel precision.
The Apple Mac was predominantly used by graphic designers at the time who universally loathed this mouse. It's a pretty obvious candidate for inclusion.
Apple G4 Cube (2000)
Oh, what a beautiful-looking machine the Apple G4 Cube was. With its clear case and small inside computer square you can be forgiven for wanting it to do well. To this day we don't like putting it amongst Apple's failures: it was simply too nice to be on a 'worst' list.
There were some reports of failures, but nothing like the Apple III and it wasn't badly designed like the Performa PowerPC (x200 series). Despite reports of cracks from heating we don't really think there was anything technically wrong with the G4 Cube (many early-run products have a few cracks while production line issues were being ironed out).
The G4 Cube just didn't sell. Apple reportedly sold a third of what it was expecting. It sat on the shelves and sat there unsold until Apple canned it.
Just why so few people bought the G4 Cube is a bit of a mystery. It was expensive, for sure, and it didn't have much upgrade potential (both well-trod and seemingly unimportant issues for other successful Apple products).
It may simply have been that the G4 didn't look powerful enough, and that companies simply weren't prepared (at that point in time) to pay for a serious machine that didn't look earnestly like a beige computer. So while consumers bought the iMac in droves, the G4 Cube remained unsold.
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