TIAH: 1990s

June 20, 1994: Apple launches eWorld, a subscription service for Mac owners that’s designed to compete with America Online and other nascent online properties. Part messaging service and part news aggregator, the early internet service gives customers access to email, a bulletin board, and software downloads and support.

Apple envisions eWorld, which runs on Macs and Apple IIGS computers, competing with heavy hitters like AOL, Delphi, CompuServe and Prodigy. Unfortunately, Apple’s online service is doomed from the start.

June 19, 1995: Apple releases the Power Macintosh 9500, a high-end Mac that boasts a second-generation PowerPC chip that’s much faster than its predecessor.

The Power Mac 9500 also packs six Peripheral Component Interconnect, or PCI, slots. They allow owners to attach hardware using Intel’s industry-standard connection. Along with seven bays for internal drives and a swappable daughterboard, this makes the 9500 the most expandable Power Mac ever produced.

June 18, 1993: John Sculley, the ex-Pepsi exec recruited by Steve Jobs to “change the world,” steps down as Apple CEO after a 10-year run.

The Apple board asks Sculley to leave after AAPL shares collapse from a high of $4.33 in 1992 to a measly 73 cents. Sculley hands over the CEO reins to Michael Spindler before briefly taking the role of Apple chairman, prior to departing altogether.

June 7, 1993: Apple debuts the PowerBook 180c, a solid upgrade that brings a world of dazzling colors to the company’s laptop line.

The 180c’s big improvement over the grayscale PowerBook 180, which launched the previous October, is its active-matrix, 256-color screen. Such a screen is something of a novelty for laptops in the early 1990s.

June 4, 1997: Mac clone-maker Power Computing hits its high point as the company’s top exec reaches an agreement with Apple concerning the forthcoming Mac OS 8.

The deal allows the company to start making moves toward an IPO as the fastest-growing PC company of the decade. Things don’t turn out well, though.

May 29, 1992: Apple demonstrates its Newton MessagePad for the first time, showing how the upcoming PDA can be used to order a pizza and pull off other time-saving tricks.

Hailed by Apple CEO John Sculley as “nothing less than a revolution,” the Newton is Apple’s first major new product since the original Macintosh shipped eight years earlier. During the first Newton demo at the Consumer Electronics Show in Chicago, Apple shows how people can customize a pizza by moving topping icons on a symbolic pie. Then they can fax the order straight from the device.

May 22, 1997: Apple spins off its Newton division, creating an independent company to manage the line of personal digital assistants. Newton Inc.’s first job? Selling the MessagePad 2000 PDA, the best Newton device yet.

But Apple also gave Newton Inc. a mandate to develop new technologies and market existing ones.

“We have a solid business plan and a strong management team in place to optimize the value of Newton technology for corporate users and take Newton technology into a new era,” says Sandy Benett, former vice president of Apple’s Newton Systems Group and chief operating officer of the new venture.

Instead, it turns out to be the beginning of the end for the ahead-of-its-time Apple PDA.

May 16, 1994: Apple launches the PowerBook 540c, one of the best laptops in the company’s history.

Part of the innovative 500 series of PowerBooks, the 540c is the laptop to own in 1994. Blisteringly fast, packed with innovative features, and offering the best notebook display on the market, it’s a triumph on every level. Although for $5,539 (over $12,400 in today’s money), it had better be.

May 14, 1992: Apple co-founder Steve Jobs‘ company NeXT runs into trouble as it loses a crucial deal with Businessland after the computer retailer closes its stores.

It comes at a time when NeXT’s luck is going from bad to worse. The Businessland closure marks one of the lowest points in Jobs’ career — before everything starts to turn around again.

May 13, 1991: Apple releases System 7, the biggest upgrade to the Mac operating system since the original Macintosh computer shipped in 1984. The new Mac OS is whip-fast, beautiful to look at, and boasts a bevy of innovative features.

The longest-lasting of Apple’s classic Mac operating systems, it will remain current until System 8 replaces it in 1997.

May 11, 1998: As part of his mission to turn Apple around, CEO Steve Jobs spells out the company’s strategy for the Mac operating system going forward. The big news is that Apple is hard at work creating a major new operating system called OS X, he says at Apple’s Worldwide Developers Conference in San Jose, California.

However, first the company will ship Mac OS 8.5 and the first customer release of an OS called Rhapsody that fall.

May 10, 1999: The third-generation PowerBook G3 comes in 20% slimmer and 2 pounds lighter than its predecessor, but most people remember the laptop for its glowing Apple logo and the “bronze” keyboard.

Although it doesn’t get a new name to distinguish it from previous laptops in the lineup, fans call it “Lombard” after Apple’s internal code name (or simply the “PowerBook G3 Bronze Keyboard”).

May 8, 1997: Apple launches the PowerBook 2400c laptop, a 4.4-pound “subnotebook” that’s the MacBook Air of its day.

The PowerBook 2400c predicts the rise of speedy, lightweight notebooks, while also paying tribute to Apple’s past. Its design echoes the original PowerBook 100. Even years later, it remains a cult favorite among many Mac users.

May 6, 1998: Apple CEO Steve Jobs unveils the original iMac, a brightly colored, translucent computer that will help save the company.

Coming just 10 months after Jobs’ new management team took over the struggling company, the iMac loudly announces that the days of Apple quietly fading into the background are over. The colorful computer marks the start of a very successful run for Cupertino.

May 2, 1995: Apple enters the wearables space with its first watch. However, the first Apple watch is a timepiece with no fitness-tracking tech, no on-screen notifications and a whole lot of 1990s styling.

The device comes two decades before wearables actually will become a thing. A regular wristwatch, the freebie gadget is available via a special mail-in offer to Mac OS upgraders.

April 26, 1996: Mac OS Copland, Apple’s eagerly anticipated but much-delayed operating system for the Macintosh, suffers a fatal blow when the senior VP in charge of the project leaves the company.

David C. Nagel, Apple’s chief technologist, previously promised Mac OS Copland would ship to users by mid-1996 at the latest. With meeting that deadline no longer possible, he leaves Apple for a job running AT&T Laboratories.

It’s yet another sign that Apple’s top-to-bottom Mac operating system upgrade is in major trouble.

April 25, 1990: Steve Jobs shuts down Pixar’s hardware division (yes, it used to have one!), ending production of the pricey Pixar Image Computer immediately.

Jobs sells the company’s hardware unit to Fremont, California-based imaging company Vicom Systems for a paltry $2 million.

April 21, 1995: Rumors swirl that Japanese camera company Canon might take over Apple in either a partial or complete acquisition.

Speculation grows about a possible deal after Apple reveals its latest earnings, which show big improvement but still fall far short of Wall Street’s expectations.

April 19, 1994: Gaston Bastiaens, the executive in charge of Apple’s revolutionary new Newton MessagePad product line, parts ways with the company.

“We can’t say whether he fell or was pushed,” says an Apple spokesman. Reports suggest that the departing Bastiaens, general manager of Apple’s personal interactive electronics division, is leaving due to his failure to make the Newton a financial success.

April 18, 1996: Apple unveils a massive $15 million promotional tie-in for the Mission: Impossible movie starring Tom Cruise.

Designed to promote the PowerBook, which Cruise uses in the spy flick, the marketing campaign comes at a particularly bad time. Attempting to climb back into the black after reporting its largest quarterly loss ever, Apple is in the middle of trying to perform its very own impossible mission. And that’s just the start of the problems.

April 7, 1997: Apple’s System 7 operating system receives its last update with the shipment of Mac OS 7.6.1.

The update brings a few bug fixes and support for Apple’s new PCI Power Macs and the PowerBook 3400. Most importantly, it marks the end of the System 7 era, which dawned way back in 1991.

April 6, 1939: John Sculley is born in New York City. He will grow up to be hailed as a business and marketing genius, eventually overseeing Apple’s transformation into the most profitable personal computer company in the world.

After a remarkable stint as president of Pepsi-Cola, Sculley will take over as Apple’s third CEO in 1983. He will run Apple for a 10-year period, guiding the creation of the revolutionary Newton MessagePad.

During Sculley’s decade at the helm, Apple will sell more personal computers than any other company. But most people still remember him for his role in kicking Apple co-founder Steve Jobs out of Cupertino.

March 28, 1996: In a dire message to Wall Street, Apple warns that it will report a $700 million after-tax loss for its most recent quarter.

Apple’s biggest quarterly loss in history, the shocking news reveals a company in far more financial trouble than previously thought. More than half the loss comes from $1 billion of unsold products.

March 27, 1995: The Radius System 100, the first official Macintosh clone, launches.

A high-end computer made by a company founded by several notable Macintosh alumni, this marvelous machine kicks off the era of clone Macs in grand fashion. However, it won’t be long until things take a turn for the worse.

March 25, 1993: Apple executive Gaston Bastiaens bets a journalist that the eagerly anticipated Newton MessagePad will ship before summer ends. The prize? Bastiaens’ well-stocked personal wine cellar, worth thousands of dollars.

The bet takes place at the CeBit trade show in Hanover, Germany. Bastiaens’ outburst comes in response to a reporter’s needling. The gamble not only gives the Newton a release timetable, but also a price target: less than $1,000.