Steve Jobs and the greatest run of products in tech history

“I’m pleased to report to you that Apple’s back on track.” It was May of 1998, and Steve Jobs was about 10 months into his second stint leading the company he’d cofounded more than two decades earlier. (It was also a bit more than a decade after that company forced him out.) Jobs took the stage at the annual Macworld conference in a white shirt and dark jacket, and told the audience the Apple team had been working harder than ever to finish up a new computer, one designed with the internet in mind. It was called iMac. “We think iMac’s going to be a really big deal,” he told the audience. He was right.

When Jobs came back to Apple in 1997, he had taken on a company in a sort of product disarray. Apple was making a lot of Macs, with no obvious rhyme or reason to the lineup; it was making, and not really selling, printers; it was trying to sell servers to businesses; it was building the Newton, a handheld device with a stylus and some big ideas about handwriting recognition. Apple made products called Quadra and StyleWriter and AudioVision and Workgroup Server and Pippin. It had certainly made a lot of very good computers, and with the PowerBook in particular, even some very innovative ones. But the company was struggling, and it was flailing.

Jobs had not been shy about this fact. “The products suck!” he’d said not long after retaking an active role in the company, according to a 2006 Businessweek story. “There’s no sex in them anymore!” Even while he wasn’t working at the company, when he was theoretically busy with Pixar and NeXT, he had spent years giving interviews about how Apple needed more innovation, about how he’d do things differently. “I’ve got a plan that could rescue Apple,” he told Fortune in 1995. “I can’t say any more than that it’s the perfect product and the perfect strategy for Apple. But nobody there will listen to me.”

Whether that ’95 plan is what Jobs went on to execute, we’ll never know. But Jobs began rescuing Apple almost immediately, rehabbing the company’s culture and kicking off a decade of almost nonstop product wins that eventually led to maybe the most lucrative and influential gadget of all time. Early on, Jobs drew up the now-famous four-quadrant grid, saying all Apple needed was a portable and a desktop product for consumers and for pros. He remade Apple’s corporate structure and gave the design team an unprecedented amount of control over how devices would look and work. (Much of it with the help of a design executive named Jony Ive.) The new Apple decided to take a new look at what computers might be, starting with a device that was colorful, shapely, translucent, and unrecognizable next to the beige boxes of parts on shelves everywhere.

Apple sold 800,000 iMacs in the five months after it hit stores in August of 1998, making it the best-selling computer in the United States at the time. That was all despite — or maybe because of — the fact that it was nothing like the other PCs of the era. It was an all-in-one device in a market filled with modular, upgradeable machines. It even ditched all the ports people actually used in favor of a newish standard called USB. Eschewing expansion had been a problem for the original Macintosh, but the iMac found a buying public desperate for a computer that didn’t take an advanced degree to figure out.

Jobs would later say the company had been 90 days from insolvency when he took it over, but its fortune appeared to turn around almost as soon as the iMac launched. And that was just the beginning. Starting with the iMac, Jobs and Apple went on one of the all-time hot streaks in business history, churning out hit products, cultural revolutions, and game-changing new ideas about the future. From that May day in 1998 to the January Macworld in 2007 when Jobs revealed the iPhone — a time you might call the iDecade — Apple was on a product tear the likes of which we’ve never seen before or since.

The summer after the iMac announcement, in 1999, Jobs debuted another remarkable new computer: the iBook. It borrowed much of the colorful iMac design, only in a rounded clamshell case that promised more portability than any other laptop ever. It shipped with built-in wireless networking, which was so unbelievable at the time that Apple’s head of marketing, Phil Schiller, sent a file from his iBook to another computer while literally leaping off an elevated stage. Jobs also swiped a hula hoop over the iBook, lest anyone think there was just a really long wire somewhere. The bit worked, and the iBook also became one of the best-selling computers in its class.

Through these years at the turn of the century, Apple also continued to refine its other computer lines. In 1999, the Power Mac lineup got an iMac-like restyling, the PowerBook got some important upgrades and design tweaks, and Apple started selling its Cinema Display standalone monitors for the first time. In 2000, the company shipped the PowerBook G4 Titanium, its best laptop to date; it also shipped the Power Mac G4 Cube, a design achievement but an otherwise pretty crummy computer. Can’t win ’em all.

Then, in 2001, Apple became an entirely different kind of company. In March, it released Mac OS X, the operating system based on the software Jobs and his team had been building at NeXT all those years ago. OS X would be the foundation for most of Apple’s gadgets for the next 25 years. Then, that October, Jobs revealed the first iPod, the device that put 1,000 songs in your pocket. “With iPod,” he said in a press release at the time, “listening to music will never be the same again.” It took a few years to prove him right, but the iPod almost immediately became a luxury object, and then an utterly ubiquitous one. The iPod was so popular that the color of its headphone cable became iconic; those silhouette ads with the white headphones remain some of Apple’s best commercial work.

Not content to sit on its success — or maybe made paranoid by how close it had once been to failure — Apple immediately set out reinventing its most successful products. In 2002, the company shipped the iMac G4, with its iconic sunflower design and flat-screen monitor. That same year, it shipped another iPod, with a few small hardware changes and one big software tweak: The iPod worked with Windows, making it available to millions of potential buyers who soon became actual buyers. In 2003, it redesigned the iPod, switching from the original curved buttons to a simple wheel underneath four buttons. Only a year later, it changed course again, this time to a much better idea: the click wheel, with the buttons integrated right into the scrolling mechanism.

By 2004, we had yet another generation of iMac — the G5, a simple screen on a stand that looks quite a bit like the iMac we still have now — plus the new iPod Mini and the iPod Photo. The next year was a big one for small gear: The Mac Mini made its debut, as did the iPod Shuffle and iPod Nano. 2006 brought the first MacBook Pro, alongside a transition to Intel chips that made Apple’s computers even more compelling. By this point, Apple’s more focused, design-led product strategy seemed essentially unstoppable, and Jobs and Ive were cementing their legends.

Apple certainly had some misses during this run: It kept shipping a line of Xserve servers that no one really wanted, its attempts at networking devices with the AirPort line never quite took off, and somehow all those designers just could not figure out how to make a decent mouse. But year after year, with Jobs relentlessly pushing the team to try new things and achieve seemingly impossible goals, Apple kept reinventing its most important and successful products, and it kept working.

All this work was adding up to something, too. Ive’s team started investigating what an Apple tablet might be like, using this new technology called multitouch. They used iBook parts and Mac OS X to build their prototypes. Then, Jobs tasked the iPod team with dreaming up an Apple phone. One of their first ideas was just an iPod with a cell connection; another was essentially an iPod that was all screen. Eventually, all these projects merged together and became the iPhone.

The 2007 launch of the iPhone was yet another inflection point for Apple. Jobs’ “these are not three separate devices” speech marked the moment the company went from successful computer maker to the biggest corporation in the world, responsible for maybe the most successful gadget of all time. It would eventually launch the iPad, too, and the Apple Watch and AirPods and plenty of other successful products. It still doesn’t hit every time — Siri and Ping and MobileMe and the Vision Pro, anyone? — but it hits far more often than most.

There’s no question that Apple’s greatest successes came after the iPhone launch. But for pure pace and level of innovation, there’s simply no beating the decade after Jobs’ return to the company. The company that once couldn’t even manage to improve on the Apple II was now inventing product after product, forcing competitors to play catch-up, then reimagined these new classics all over again a few years or even months later, to somehow even bigger acclaim and bigger sales. We may live now in the world the iPhone made, but the iDecade was truly Peak Apple.