Three 1990s Macs that defined my life—and explain Apple’s history

Welcome to Dial Up, Mashable’s most excellent look at technology in the ’90s, from the early days of the World Wide Web to the clunky gadgets that won our hearts. 

For much of the 20th century, the western world seemed to mark progress through the design of its cars. From the 1910s through the 1980s, each decade offered radical new looks that defined their times, even now (think round rims in the ’40s and  sharp fins in the ’50s). 

But the 1990s were different. Cars became the same dull, dependable steel boxes they are today. If you wanted to understand a rapidly changing high-tech world at the end of the 20th century, you needed to watch what was happening to home computers.

Apple, especially, went through an incredible fall and rise in the 1990s, one that took the company from boxy desktops to troubled laptops to an unusual design that would change the company’s fortunes. And I, a computer-free school kid in the north of England at the beginning of the decade, ended it as the Apple reporter for a top U.S. magazine. It’s safe to say that I never would have made that journey without these three Macintosh machines by my side.

1. The Macintosh IIsi 

In March 1994, I purchased my first Macintosh — no need to specify that it was a desktop, for there was no other kind of Mac at the time — from my friend and fellow student Ed. Apple had discontinued the Macintosh IIsi the previous year, and was now on the significantly speedier model, the Macintosh Centris 610, which Ed — the nerdiest tech-head I knew at Oxford — wanted instead. 

But this was not an era when such things mattered to the consumer. The launch of a new Apple product was not reported breathlessly in newspapers. There were no Apple stores. There was barely any internet. I doubt I’d even heard of the Centris 610 or had any sense of what the model names meant. (The “SI” in IIsi apparently either stood for “sound input,” because it came with Apple’s first microphone, or more bizarrely, “sleek, integrated video.”) 

Computers were universally seen as interchangeable beige boxes. (Macs were more off-white than beige, but still did little to dispel this notion.) If it could boot up, it wasn’t obsolete. Ed was selling the IIsi for £300. He was throwing in a color monitor, in an era when most were black and white. As John Travolta told Samuel L. Jackson in that year’s best film, peering into a mysterious gold-lined suitcase: “Yeah, we happy.”

I had no attachment to Macs before ’94. As a kid I had a second-hand, much-maligned British computer called the Amstrad. My college’s “computer kitchen” used PCs, exclusively, to access the still obscure World Wide Web, which we surfed on Mosaic browsers via a cool new search website, Yahoo.com. But there were a handful of Macintoshes at the venerable weekly Oxford student newspaper, Cherwell, where I had just finished a semester as editor-in-chief, and Ed was our IT guru. It’s no exaggeration to say they changed my life.

Macs became associated with long, hazy nights of cigarette smoke and endless cups of tea and the sounds of Britpop on a tinny radio. They weren’t internet connected, but nobody cared. We used them to hack away at chunks of excitable reporting in Microsoft Word 5.1 (the story usually delivered in person by the reporter with a 3.5-inch floppy disk), then dropped the text into what was then the world’s best layout program, Quark Xpress. I spent too much time touching up the photos from our crack team of snappers in a new-to-me program: Photoshop 2.5. 

It was a revelation: a handful of editors, a handful of Macs, the tiniest bit of proficiency in point-and-click publishing software, and we could turn out most of a weekly newspaper in one night. 

Naturally, I was keen to see what I could do with Quark and Word on Ed’s Mac. I got an unofficial copy of the latter on a disk from our production manager, who had unofficially copied it from his professor, who happened to be the internationally famous biologist and Selfish Gene author Richard Dawkins. For the next two years, every time I booted up Word, Dawkins’ name would appear on my screen as the registered owner. (The statute of limitations has presumably passed, and Dawkins was later unmasked as a notorious Islamophobe, so I don’t feel too bad about revealing the piracy now.)

The good stuff was just a double-click away, alluring as a Vegas casino

It soon became clear that Macintosh ownership was a double-edged sword. On the one hand, I became a more productive writer. Essays and posters and stories and proto-memes poured forth. I even took up writing poetry. (Charles Bukowski, the famously foul-mouthed American poet, also bought a Mac IIsi, and found it vastly improved his output. His stuff was better.) When President Clinton visited Oxford that June, his helicopter gunships touching down in my college’s fields, I figured it a good day to switch the handwritten diary I’d kept for 13 years into digital format, typing my longest entry yet for the momentous occasion.  

On the other hand, as I often lamented in those diaries, the good stuff was just a double-click away, alluring as a Vegas casino. Screen addiction did not start with the age of the smartphone. The Mac IIsi may have had a mere 35 megabytes — that’s right, kids, I said megabytes — in its hard drive; I still think of this fact today whenever I happen to download a file that’s roughly 35MB in size. (That’s my entire first Mac, I think, and it downloaded in a couple of seconds.) 

But 35MB was more than enough room for dozens of addictive little programs, plus a couple of games that have never been surpassed when it came to heroin-like addictions in my life: Sim City 2000 and the original Civilization.

In fact, I became so hooked on Civilization before my finals that I knew I had to eliminate the problem and get clean. So I made a pact with myself: I could play for one last night for as long as I liked, but as soon as I went to bed, I had to drag the entire Civ folder into the trash. 

Sunrise the next morning found me clicking “next turn,” rocking back and forth, weeping tears of tiredness, muttering “just delete it” to myself over and over. I finally found the strength to hit apple-Q, drag the folder into the trash and empty it. 

Within seconds, Oscar the Grouch came out of the top of the trashcan icon, and sang one of his two stock phrases: “Oh, I love trash” or “I love it because it’s trash.” 

Because that was the thing about the IIsi: it was eminently customizable. You could pimp it out with your own icons and sounds and animated GIFs (yeah, kids, we had GIFs, you’re not special). I dove into a bunch of programs on a pile of disks Ed had bequeathed me. Soon enough my Mac shut down to the sound of Arnold Schwarzenegger: “I’ll be back.” It started up with the first words of hip hop artist Guru on his groundbreaking 1993 album Jazzmatazz — “Peace, yo” — while an app named Bongo Bob dispensed a quote of the day that was often a random line of Grateful Dead lyrics. 

Error messages arrived with a Homer Simpson “d’oh!”, which in the 1990s was never not hilarious. And constant hilarity was a necessary thing, considering how frequently one’s home computer could throw up error messages in those frontier days.  

Then of course there was the king of screensavers, After Dark — one of the last big applications that launched on Mac before it launched on Windows. You may recall After Dark as the one with the flying toasters, but it was so much more than that — it was bubbles and cracks and glitches suddenly filling the screen, playing with our fears that computers were fragile and could break at any second. It was also soothing aquariums and fractal trees and multiple Looney Tunes and Star Trek situations. 

And it too was customizable, interactive to a degree that puts today’s screensavers to shame. If you remember adjusting the toast in the flying toaster screensaver to your preferred level of toasted, then you know well our ability to distract ourselves with minutiae did not begin with the internet. 

The next year I got a CompuServe account and a 56k dial-up modem, and suddenly personal email was a thing that existed. Meanwhile, Microsoft released the ridiculously hyped Windows 95, and Apple began its perilous mid-90s dance with irrelevance that almost killed the company. My next Apple product would show signs of the struggle. 

2. The PowerBook 190C

It was the starry-eyed immigrant cliché, slightly upgraded. In August 1996, I arrived in New York City with two suitcases, a dream, and a brand-new, 5-pound Apple laptop … that crapped out the first morning in my new homeland. 

The laptop in question was the PowerBook 190C. The C denoted the fact that it boasted a color screen, because in those days you could choose cheaper laptops with monochrome screens (little did I suspect that Apple users would one day deliberately hobble their devices, turning iPhone screens black and white as an aid to productivity). 

Had I learned anything from my IIsi and its colorful distractions, I should have gone for the regular black and white PowerBook. I was enrolled in Columbia University’s famously intensive one-year graduate course in journalism — a master’s degree compacted into nine months that would leave little time to sleep. A black and white screen would have helped to encourage some serious focus on the writing, especially once a school friend gave me a disk with Civilization on it. (Just one game, I reasoned. Just take the edge off.) 

But the Web was everything by 1996, and it was an increasingly colorful experience. The school held out the gauzy notion that its new New Media elective would have us editing brief online videos; I should, it seemed clear, be ready to do that. 

The hype of the Dotcom era was starting to touch everything. I was seduced by an ad that featured a team of explorers lost in the jungle — but lo and behold, by wiring their laptop up to one of those new flip phones, they’re online and arranging a rescue! That was a big factor in my decision to get a PowerBook: Pretty soon, we would be browsing the internet wirelessly, so why plug a beige box into a wall when you could go anywhere? 

(In fact, cellular connectivity was not nearly as easy as advertised. WiFi wouldn’t enter the mainstream until at least 2000; even then it was a clunky, mostly home-based system.)

The 190C wasn’t exactly sleek or discreet. I took it to a coffee shop — a laptop in a New York coffee shop, imagine that — and was met with sniggers from the next table over, where someone started humming the theme to the recent reboot of Mission Impossible. That year, Apple had famously paid $15 million to have Ethan Hunt (Tom Cruise) use a PowerBook (the next-generation 5300ce model) in the film’s iconic dangling-from-the-ceiling scene. 

Unfortunately, the 5300 laptops suffered a couple of high-profile battery fires after the movie came out, one of them at the home of an Apple programmer. Hunt was more lucky to get out of that room alive than he knew. 

My main PowerBook woe was nothing so dangerous: It was merely that the screen stopped working, repeatedly. On the first of many visits to TekServe, an old school Manhattan Apple support store, a proto-Genius said a wire must have come loose in transit. The laptop had been on a couple of planes in the past month. I’d asked my American girlfriend to buy one and bring it over, since paying the U.S. cost of the laptop plus the cost of her flight to the UK was cheaper than buying one over there. But by the time she arrived, we were well on the way to breaking up for other reasons, and the visit was far from pleasant. 

With that emotional toll and the frequent screen outages, the laptop began to feel cursed. As it turned out, it would not be the most cursed Apple device I ever bought; that dubious accolade would either have to go to my 2009 MacBook that was on board a FedEx plane that blew up on the runway (Fedex’s first fatal crash in 30 years), or its replacement, delayed by a volcano in Alaska that grounded air traffic. Its arrival at my San Francisco home coincided with a brief earthquake. I immediately named it MACBOOK OF DOOM. 

I still own the 190CS, alone among the Apple devices mentioned here. For this story, I dug it out of the garage, fished out its surprisingly slim charger from a box of cables, and was astonished to discover that the 23-year-old Apple laptop — now older than I was when I first arrived in America that summer — still works just fine. On the inner plastic screen bezel were a bunch of telltale concentric circles; I remembered there were times when I literally had to attach a clamp to hold its faulty wiring in place. But no longer. 

It booted up, problem free, and spat out the first disk I can remember seeing in decades. On the desktop were a bunch of Word files untouched since 1997 and 1998, when I began working at Time magazine. It seems I had last used it to report from the World Cup in France in the summer of ’98, using then-sporadic French dial-up internet. There was a fax modem card installed, but it was missing the cable that plugged into a phone jack; besides, who has a phone jack any more? 

The fastest way to get files off this device now would be to take iPhone photos of the screen and run them through an optical character recognition app. Let that janky workaround serve as a reminder: We don’t think about our digital data being isolated on old devices in old formats until it is. 

3. The first iMac 

In August 1998, I made the leap from owning Apple gadgets to writing about them. It was an interesting time to do so. Steve Jobs had returned to the company he founded after Apple CEO Gil Amelio purchased Jobs’ second company, NeXT, in 1997. He then ousted Amelio in an audacious boardroom coup. Serving only as interim CEO, or so he claimed for years, Jobs had immediately halted the practice of licensing other computer makers to produce cheap machines that ran the Macintosh OS. 

Conventional wisdom said he was insane. Microsoft ruled the world because it let other companies handle the beige boxes, and instead concerned itself with getting Windows software onto as many of them as possible. Jobs had barely kept Apple alive by getting his old frenemy, Microsoft chief Bill Gates, to promise to continue making Microsoft Office for the Mac, in return for a significant chunk of Apple shares. Now he was returning to the same pricey Apple design strategy that had dogged the company’s sales the last time he was in charge? It made no sense. 

Then one day a box containing something called an iMac showed up at my desk in Time Inc., along with an offer for a phone interview with Jobs. It was a sign of the times that we decided the interview wouldn’t even run in Time magazine proper, but in a (now defunct) separate tech magazine for subscribers called Time Digital. This sense that Apple was nowhere near the center of the tech news action would persist for years; I would have to fight to get a single page in Time proper to cover the launch of the iPod in 2001. 

I’d like to say we were instantly awed by the iMac, that now-famous Jony Ive design in its original Bondi Blue housing. But at first it produced as much sniggering as a Mission Impossible laptop. Many of my co-workers saw the colorful plastic and assumed it was a computer for kids. You’d have to be a hardcore Apple fan to love the hockey-puck mouse. And it was surprisingly slow to launch. 

“Eh,” said my cynical editor when he saw the iMac boot up for the first time. “My [Windows 98] laptop does that in seconds. It’s like, ‘I’m here! I’m ready! What do you want?’” 

The Jobs interview didn’t go much better. It was the first of about 20 times I would sit down with the Apple boss, and I hadn’t yet got the memo that he was famously abrasive with journalists. Ironically, it was a question that reflected my love for Apple that tipped him over the edge. “You’ve said that you want Apple to be as good at design as Sony,” I reminded him, but added that I was mystified as to why Sony, the company whose flagship product was a toy robot dog, was seen as the be-all and end-all. “Isn’t that a rather limiting ambition?”

Jobs exploded. “That’s a stupid question,” he said — one of his favorite phrases, I later discovered. Instead of answering it, he went on an almost Trumpian tirade against the publication the interview would appear in: “I know lots of people who read Time magazine! I don’t know anyone who reads Time Digital!” Apple PR called to apologize the next day.

Of course, with the benefit of hindsight, it absolutely was a limiting ambition. Already, behind the scenes, Jobs and Ive were planning much greater things. A new iMac with a flatscreen on a “sunflower stalk” was first. Then the revolutionary MP3 player known as the iPod, and the revolutionary 99-cents-a-song iTunes Store, which would soon be followed by a top-secret touchscreen tablet project. 

Its designers beavered away in the strictest secrecy inside Apple’s Infinite Loop HQ for years, eventually morphing it into a touchscreen phone that would change the world. Sony, meanwhile, is better known for an uneven slate of superhero films than for any phone or computer. 

Cranky Jobs notwithstanding, I came to love the iMac test unit that I chose to buy one of my own, in purple, in 1999. It wasn’t just my first iMac, but also my first DVD player and first CD burner. You may recall the “Rip. Mix. Burn” ad campaign that effectively aligned Apple with that scourge of the music industry, Napster, but also allowed it to present a solution in the form of the iTunes Store. 

That all started with this machine. Apple pushed the iMac as your “digital hub,” a device that could store your digital photos, your digital songs, your homemade films. And that’s how the company crept out of Microsoft’s shadow: Let them make your boxy work terminals, we’ll make your home computing cool. 

And it was — far cooler, faster and more efficient than either of the Apple machines I’d owned so far. Something about the beanbag-like design of the iMac made you want to hug it (when it was sleeping, at least; the rear of the cathode ray-tube would make the device too hot to hold when powered up). 

But the plastic carrying handle stayed mercifully cool, which made the iMac surprisingly portable. You could use it to watch DVDs in bed, as I did with my new New York girlfriend, both of us guffawing at how ridiculous and brilliant this whole setup felt. It seemed like what it was: a glimpse of the future. 

As 1999 drew to a close, it was becoming far easier to believe that the 21st century would belong to Apple.