These fumbles helped pave the way for the world’s coolest mobile devices

Looking at Apple's successes right now, it seems they can do no wrong. But that wasn't always the case -- Cupertino has released some flubs in its day. But those missteps helped pave the way for the awesome products we know and love today. And is a mistake really a mistake if you learn something from it? 

The mobile universe is a great place to start...

The Newton

The Newton may be gone, but it’s anything but forgotten.

Until the iPod, the Newton was Apple’s most famous product since the original Mac. Unfortunately, it was known more for its long-delayed launch and subsequent failure in the marketplace than for helping to spark the mobile computing revolution.

Back in 1987, Steve Jobs was out of Apple, and CEO John Sculley was looking for something to boost the company’s flagging fortunes. He found it in the Newton, an ambitious internal project to create a stylus-controlled touchscreen computer that could replace the Mac. But development of the Newton’s bleeding-edge handwriting recognition software kept it from being announced until 1992, and even then the first Newton device didn’t ship until the following year.

The MessagePad launched at $699 to a cool reception. The problem wasn’t its chunky size (4.5x7.25 inches) or even its battery life (a respectable 14 hours on 4 AAA batteries). Flaky handwriting recognition and a poky 20MHz processor gave the world a bad first impression of the Newton, and sales never quite recovered. Worse, Newton’s delays gave rivals like Palm time to develop and ship competing PDAs, some of which sold for less than half the cost of a MessagePad. But Newton’s many strengths, like the ability to send and receive faxes and email, organize contacts and calendars, and--when it worked--turn scribbled notes into editable text gained a loyal, if modest, following. Over the years, the Newton faithful were rewarded with improved handwriting recognition and increasingly powerful (and expensive) hardware. But by the time Steve Jobs returned to Apple in 1997, the writing was on the wall, and the Newton project was canceled.

A decade later, fans were still banging the drum for Apple to reenter the tablet market it helped create. They got their wish with the one-two punch of the iPhone and iPad, both of which benefited from avoiding the mistakes of the Newton era. By shipping on time, Cupertino gave competitors like RIM and Microsoft no head start to catch up (and they still haven’t). By entering an existing market--smartphones--Apple gained profits and mindshare that helped it build a new platform from scratch with the iPad. And by focusing on delivering a few core features with each product, Apple could afford to wait to add more complexity, like the game-changing App Store, until they were absolutely ready.

The ROKR E1

If you want something done right, do it yourself.

While not technically an Apple product, the Motorola ROKR E1 was the first cell phone with iTunes compatibility -- and it was the worst. Even in 2005 its ho-hum candybar design was nothing to write home about, but it was the ROKR’s clunky navigation, lack of USB 2.0 connectivity, and arbitrary 100-song limit that kept music lovers away in droves. If nothing else, the experiment was proof that Apple had to enter the phone business with a device of its own if it wanted things done right. That’s worked out pretty well so far.

The QuickTake

Customers never took to the QuickTake, but Apple rebounded.

Just like its contemporary the Newton, Apple’s QuickTake, one of the first consumer-level digital cameras, didn’t catch on. Whether it was because of a price tag north of $600 or early models’ lack of focus controls and removable storage, the line was canceled just three years after its 1993 introduction. But Cupertino never abandoned digital photography, and they continued bundling advanced optics into products like 2003’s iSight webcam. Shutterbugs haven’t abandoned Apple, either. Today the iPhone 4 is the most popular camera on Flickr, with the iPhone 4S, one of the best consumer cameras on the market, not far behind.

The Original iPad Case

No, that’s not Darth Vader’s diary.

There was nothing especially wrong with Apple’s iPad case -- how did they get it to feel like suede, anyway? -- except it covered all that gorgeous glass and aluminum. Apple’s sequel for protecting the iPad 2, Smart Covers, is a classic case of Cupertino refining form and function into something too cool not to use. Sure, swapping the all-enclosing sleeve for magnetic latches lets us show off our iPads while providing a sturdier stand. But throw in a range of colors and materials, plus the handy wake-on-open feature, and everything just clicks.

The 3G iPod Shuffle

Was it an iPod or a lost cufflink?

Is there such a thing as too much simplicity? Music lovers seemed to think so when the 3G iPod shuffle, missing nearly all the buttons from previous models, was released in 2009. Apple hoped users would take to using pre-Siri voice recognition to navigate playlists, and headphone controls to skip tracks and adjust the volume. Reactions, including our own review, were mixed. Apple went back to the drawing board and brought buttons back with 2010’s compact, clickable 4G shuffle. That year the 6G iPod nano with Multi-Touch debuted with physical volume buttons. Coincidence? Maybe. Simple? Definitely.

MobileMe

Before iCloud, there was MobileMe (and .Mac).

Nothing shows Apple’s willingness to stick with something for as long as it takes to get it right like MobileMe. After launching in 2002 as .Mac, Apple’s web-hosting, online storage, and data-syncing service gradually added awesome new features like Find My iPhone, gorgeous webmail, and even Windows compatibility. Subscribers with iPhones and multiple Macs knew it was a sweet deal, but the $99 annual fee kept most people away. Cut to 2011’s iCloud launch, and Apple had winnowed its cloud-based offerings to a lean-and-mean suite of services with an iOS focus -- for free.