Notable for: Pen computing and wireless too!

This was one of the early tablet computers and was packed with wireless support, too. It ran an early operating system called PenPoint, developed by the GO Corporation, which never caught on. Ironically, AT&T is now the hot ticket with its exclusive contract to sell Apple's iPhones. The same designer of the EO, Frog Design, was also involved in several Apple products too.
Notable for: Its current version is sooo much worse that the original.

I have been a user of iMovie for many years and thought it was one of the best pieces of software that I have ever used for any purpose, which is high praise given how many different products that I touch. But when Apple updated the product a few years ago iMovie went from doyenne to dog overnight. It is an example of how to take a great piece of software and totally trick it out to the point where it is unusable, as well as removing features that made the product a joy. Why, Apple, why?
Notable for: Lousy handwriting recognition, but hey, they tried.

In the early 1990s the PDA market was just starting, and Apple's attempt at delivering a device that would recognize handwriting quickly got enshrined in a series of Doonesbury cartoons because it couldn't really recognize handwriting very well. It also didn't help that it had a very short battery life and a high price tag, although it can still be found in a few odd places such as survey instruments. The product lasted until 1998, and then Apple got onboard the iPod generation to redeem itself.
Notable for: First smartphone.

One of the first smartphones with a full QWERTY keyboard. This phone is probably more well known for its cameo role in a James Bond movie than for any ordinary user. RIM's BlackBerry wouldn't appear for a few more years, and now has a hefty share of the market.
Notable for: It was cute and belonged in the kitchen.

Audrey was the original kitchen computer for people that couldn't deal with a full-blown PC, yet could still shell out $500 for a machine with a wireless radio and all 32 MB of RAM. (Gives you some perspective on $300 Netbooks, yes?) It had the unfortunate timing to launch before the dot-com crash, and to come from 3Com, which at the time was still trying to figure out how to sell consumer electronics (they had purchased a modem company and Palm too). The device lasted all of seven months before it sank.