I’m an inveterate Apple fanboy. I buy nearly every odd-numbered iPhone release because I can’t justify spending $1,000 or more on a new phone every year anymore, and I upgrade my MacBook Pros every few years. I’ll be the first to admit that the speeds-and-feeds benefits of upgrading are fairly limited in Apple’s case. You’re basically buying a slightly faster version of the same machine every time. But there is definitely a reason to upgrade as batteries age, performance begins to lag and the general usability of older models degrades.

This upgrade path, familiar to anyone with an Apple fetish, is fine. It’s natural. It works. And one day, when it no longer makes sense to buy one of the best-designed laptops with some of the best specifications and the best operating system in the world, I’ll be the first to dump my MacBook for a Dell or an intracranial link or whatever comes next.

Given Apple’s recent product launches, however, I’m beginning to wonder whether that day is coming sooner than I expected.

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There was a brief period around the year 2000 when technology companies seemed convinced that everything in the physical world needed a connection to the internet. Magazines, newspapers, advertisements and product packaging were all opportunities to send consumers to websites, provided somebody could invent a sufficiently complicated way to get them there.

You’ll notice what I just wrote: they wanted to put magazines and newspapers on the Internet. But not in the way we think about them now. Print publishers saw the Internet as a gaping maw about to swallow them up, a Neverending Story-esque Nothing that would destroy their bottom lines. And they are absolutely right.

The solution? Why not connect paper to the Internet in a way that would give readers just enough of an online connection but keep them headed to Borders to pick up the latest issue of Cat Fancy.

Enter the CueCat, one of the strangest computer accessories of the dot-com era.

The CueCat was a small barcode scanner shaped like a cat. It connected to a computer, sat on your desk and waited for you to scan special barcodes printed in magazines and advertisements. The accompanying software would then open a related website, saving you the supposedly arduous task of typing a URL into your browser.

It was a solution to a problem that most people didn’t know they had. But for a short time, the CueCat had some of the biggest names in American publishing behind it.

A cat-shaped bridge between print and the web

The CueCat was developed by Digital Convergence, a Dallas-based company led by entrepreneur J. Jovan Philyaw, who later became known as J. Hutton Pulitzer. The device launched in 2000, at the height of the dot-com boom, when investors were willing to fund almost anything that promised to connect traditional media with the rapidly growing internet.

The idea was relatively straightforward. Instead of printing a website address in a magazine, an advertiser could print a special barcode. Readers would scan the code with their CueCat, and Digital Convergence’s software would direct their browser to the appropriate online destination.

The company called this process cueing.

The hardware itself was wonderfully peculiar. Its elongated body resembled a crouching cat, with a scanning window at the front and a tail-like cable at the back. Early units connected through a PS/2 keyboard interface, allowing the scanner to send data to the computer much like a keyboard would.

The CueCat wasn’t designed to be an independent device. It needed a computer, the company’s software and an internet connection to do anything particularly useful.

That was a lot of infrastructure to replace typing something like example.com. But, as you might recall, URLs were still deeply confusing. Further, there was no way to attribute a click to a certain magazine. If an advertiser wanted to see if someone visited their site because of a magazine ad, they needed some way to attribute interest. All of this was very primitive, to be clear, but the CueCat promised at least some level of attribution.

RadioShack and the magazine industry get involved

Digital Convergence wasn’t simply a tiny startup handing out novelty gadgets. The company secured major commercial relationships, including backing and distribution through RadioShack and partnerships with publishers.

RadioShack distributed CueCats through its stores, while magazines such as Wired and publications associated with Forbes participated in the program. Millions of scanners were produced and distributed, often at no cost to consumers.

The strategy was to build an audience first. If enough people had a CueCat on their desks, advertisers and publishers could pay to connect printed material to online content.

Digital Convergence also experimented with codes embedded in television and radio audio, extending the idea beyond printed barcodes.

In theory, it was an early version of the physical-to-digital advertising systems we now take for granted. In practice, it required consumers to install special software, register the device and keep a dedicated scanner next to their computers.

The inconvenience was considerable, particularly when the alternative was simply reading a web address.

When the cat got hacked

The CueCat had another problem, and this one was considerably more serious than the inconvenience of scanning magazine pages.

To use the official software, consumers had to register with Digital Convergence. Each scanner carried a unique identification number that could be transmitted along with scanned codes, raising concerns about the company’s ability to track individual users and their reading habits.

In September 2000, a security vulnerability exposed registration information associated with approximately 140,000 users. The incident attracted criticism at a time when consumers were becoming increasingly aware of online privacy, and Digital Convergence offered affected users a $10 RadioShack gift certificate.

Meanwhile, programmers discovered that the hardware was more useful than the company’s intended application. By modifying the scanner or using alternative software, they could turn it into a general-purpose barcode reader.

Suddenly, a device designed to send consumers to advertisers’ websites could be used to catalogue books, organise CD collections or scan grocery products. Wired documented several of these projects in December 2000, including applications that retrieved book information and product details from online databases.

Digital Convergence initially resisted this experimentation, asserting restrictions on modifying its hardware and software. That only generated more criticism. The company had given away enormous numbers of scanners, and hobbyists were finding uses for them that were arguably more practical than the original business model.

In a strange way, the CueCat became successful as a piece of hardware precisely when people stopped using it as intended.

The collapse

By 2001, the CueCat’s problems were becoming impossible to ignore. Digital Convergence had spent heavily on distribution, software and partnerships, but there was little evidence that consumers wanted to make barcode scanning part of their daily internet use.

The company had attracted roughly $185 million in investment, according to a retrospective published by Hackaday. But giving away millions of scanners was expensive, and the advertising business needed to justify that investment never developed as hoped.

In May 2001, Digital Convergence laid off most of its workforce. Major investors began writing off their investments, and the company ultimately collapsed.

The scale of the failure was remarkable. Millions of CueCats had been manufactured, with large quantities eventually ending up as surplus electronics. In 2005, a liquidator offered two million unsold units at just 30 cents apiece in bulk.

For a device that had once been promoted as a new way to navigate the internet, that was a fairly undignified ending.

The CueCat was a QR code with extra steps

The most interesting thing about the CueCat is that its underlying idea wasn’t particularly bad.

Today, scanning a printed code to open a website is completely ordinary. Restaurants use QR codes for menus, advertisers put them on posters and manufacturers print them on packaging. Most smartphones can recognise these codes using their built-in cameras, without dedicated hardware or proprietary desktop software.

The CueCat anticipated that relationship between physical media and digital content, but its implementation was unnecessarily complicated.

You needed to own the scanner, connect it to a computer, install the software, register an account and scan a compatible barcode. The computer also needed an internet connection, which in 2000 frequently meant dial-up.

QR codes eventually succeeded partly because smartphones removed nearly all those barriers. A camera was already in your pocket, and opening a website required little more than pointing it at a printed square.

There was also a fundamental difference in how the systems operated. CueCat’s original model relied on Digital Convergence’s infrastructure to interpret codes and route users to websites. Standard QR codes can directly encode web addresses, making them far less dependent on one company’s servers.

The CueCat wasn’t the only precursor to modern QR-code marketing, but it remains one of the most memorable.

A strange little piece of internet history

Today, the CueCat survives as a collectible and a curiosity among retrocomputing enthusiasts. Some owners have modified the devices to work as ordinary barcode scanners, while others keep them as reminders of an era when internet companies were willing to spend extraordinary amounts of money on speculative consumer technology.

And the CueCat deserves to be remembered for more than its failure.

It demonstrated how difficult it was to persuade consumers to adopt dedicated hardware for a task that offered only a small improvement over something they could already do. It also illustrated the risks of tying a physical product to a proprietary online service, particularly when that service depends on a business model that hasn’t been proven.

Perhaps most importantly, it showed that users sometimes understand the value of a device differently from the company that created it.

Digital Convergence wanted the CueCat to revolutionise advertising. Hackers wanted a cheap barcode scanner. Consumers mostly wanted to visit websites without having to plug a plastic cat into their computers.

Twenty-six years later, it’s hard not to appreciate the absurdity of the whole thing. The CueCat was an attempt to build a bridge between print and the internet, backed by major publishers and millions of dollars.

The bridge eventually got built. It just didn’t need the cat.

Before every smartphone became a featureless rectangle of glass, there was the T-Mobile Sidekick. It was chunky, colorful, and equipped with a screen that flipped open to reveal a full keyboard. It was also one of the first phones that made being online all the time feel normal.

The Sidekick was more than a phone. It was a portable instant messenger (AIM was the service of choice), email client, web browser, and social hub. At a time when most people were still struggling to type text messages using a numeric keypad, Sidekick owners were firing off messages on tiny QWERTY keyboards, chatting with friends, and checking their email from practically anywhere.

The best part? Unlike the stodgy Blackberry and its janky operating system, the Sidekick was fun. Some models had a little rollerball that let you pick the app you wanted to launch and the entire package was trendy, colorful, and fun.

For a few years in the 2000s, it was arguably the coolest piece of technology you could carry.

The Beginning: Danger, Inc. and the Hiptop

The Sidekick story begins in 1999 with a Silicon Valley startup called Danger, Inc. Founded by Andy Rubin, Joe Britt, and Matt Hershenson, the company wanted to build a mobile device designed around internet connectivity rather than traditional phone calls.

Rubin would later become famous for co-creating Android, but his earlier work at Danger helped establish many of the ideas that would define modern smartphones.

Before the T-Mobile Sidekick became one of the most recognizable mobile devices of the 2000s however, it was supposed to be a $1 keychain accessory that received data over FM radio.

At the time, the internet was dominated by portals like Yahoo and AOL, which offered email, calendars, news, and other services through a single website. These companies wanted users to spend as much time as possible on their sites, but there was a problem: most people could only access the internet from a desktop computer.

As one early Danger employee, Chris DeSalvo, recalled, “The huge problem facing portal developers then was that they only had access to users while they were at their desktop computer, often only at work.”

Danger’s first answer was a small device code-named Peanut. It had a basic LCD screen and a few buttons, and its purpose was to carry information from a user’s online account, including calendar entries, to-do lists, and recent emails.

The business model was unusual. Danger planned to sell Peanut to consumers for just $1, then charge internet portals a monthly fee to keep the devices updated. The hope was that Yahoo and other portal operators would pay to keep their users connected even when they were away from their computers.

Getting information onto Peanut required some creative engineering. Users could place the device in a dock connected to a computer’s serial port, then visit a website that used a custom browser plugin to transfer data. Danger even experimented with synchronized advertising, displaying an advertisement on the computer while showing a related animated ad on Peanut’s tiny screen.

The company also planned to deliver updates wirelessly using FM radio subcarriers. Danger would lease bandwidth from radio stations across the country and broadcast small amounts of data to devices within range.

The technology worked, and the company considered ways to use it for location-based advertising. Retailers could install low-power transmitters that would send promotional offers to people walking nearby.

“We liked to talk about folks walking past a Starbucks, having their Peanut go <ding>, looking down at it, and seeing that they’d just received a 10% off coupon that was good for the next 5 minutes,” DeSalvo said.

Unfortunately, FM radio was a poor system for delivering personal data. Danger would have needed agreements with radio stations across the country, along with equipment installed at each location. The system also had no reliable way to determine where users were traveling.

Danger considered broadcasting a user’s information from the transmitter closest to their home ZIP code, then gradually distributing updates to other cities in case they traveled. It was complicated, expensive, and unreliable.

“Anyway, it turned out to be a really bad idea,” DeSalvo said.

The breakthrough came when one of Danger’s venture capital partners calculated that building a nationwide FM data network could cost roughly as much as developing a two-way wireless device using GSM cellular networks.

The newer GPRS data service offered something Peanut could not: a device that could both send and receive information without being connected to a desktop computer.

Danger also found a willing network partner in VoiceStream, a relatively small wireless carrier that had emerged from Western Wireless. VoiceStream was looking for devices that could demonstrate the potential of its mobile data network. The company would later be acquired by Deutsche Telekom and renamed T-Mobile.

With a cellular network available, Danger abandoned Peanut and began developing an entirely different product.

“We weren’t exactly sure what it was going to be, but we all knew that we wanted one,” the DeSalvo said. “Since there wasn’t really anything in the marketplace to model ourselves after we just built the thing we all wanted to have.”

That decision eventually produced the Hiptop, launched in 2002 and sold in the United States as the T-Mobile Sidekick.

The original Sidekick had a monochrome screen, a physical keyboard, a scroll wheel, and a distinctive rotating display. Instead of opening like a clamshell phone, the screen swung sideways to expose the keyboard underneath.

The mechanism was instantly recognizable. Opening a Sidekick became part of the experience, and the movement itself was almost as satisfying as using the phone.

More importantly, the Sidekick was built around data. It offered web browsing, email, instant messaging, and a constantly connected experience over T-Mobile’s GPRS network.

The Sidekick II and the Birth of a Cultural Phenomenon

The original Sidekick was a technological curiosity. The Sidekick II, released in 2004, turned it into a cultural phenomenon.

Manufactured by Sharp, the second-generation device featured a slimmer body, an integrated camera, and a more refined design. It retained the rotating screen and full keyboard, which had become the Sidekick’s defining features.

By this point, the device was finding an audience among teenagers, musicians, actors, and celebrities. Paris Hilton famously carried one, and the Sidekick became a fixture in celebrity photographs and entertainment coverage.

Part of its appeal was practical. AOL Instant Messenger was enormously popular, and the Sidekick made it possible to maintain conversations without sitting at a computer. Its keyboard made long messages easy to type, while its interface put communication at the center of the experience.

There was also a sense of exclusivity. BlackBerry devices were associated with executives and businesspeople. The Sidekick was for people who wanted to talk to their friends.

The phone became a fashion accessory as much as a communications device. Special editions, including collaborations with Juicy Couture and tattoo artist Mister Cartoon, reinforced that identity.

In retrospect, the Sidekick II helped establish the idea that a smartphone could be a personal expression rather than simply a business tool.

The Sidekick III and the Peak of the Platform

The Sidekick 3 arrived with a new trackball navigation system, Bluetooth connectivity, a music player, and support for faster EDGE data connections. It also offered expandable storage, bringing the device closer to the multimedia smartphones that would soon dominate the market.

T-Mobile continued expanding the lineup. The budget-oriented Sidekick iD appeared in 2007, followed by the larger-screen Sidekick LX and the Motorola-manufactured Sidekick Slide.

The Slide abandoned the traditional rotating display in favor of a sliding mechanism, but the LX retained the familiar design.

The Sidekick LX became particularly popular thanks to its larger screen, distinctive appearance, and emphasis on messaging. By this point, the Sidekick had developed something that few consumer electronics products achieve: a recognizable identity. You could spot one across a room.

That identity was also becoming a limitation. The Sidekick’s software and hardware were designed around messaging at a time when the broader smartphone market was beginning to change. That said, what the Sidekick was doing before anyone else was vitally important and points to the future of mobility.

The Sidekick Was an Early Cloud Smartphone

One of the Sidekick’s most important innovations was largely invisible.

Danger designed its platform around servers that synchronized information between the device and the internet. Contacts, calendars, messages, and other information were tied to online services rather than existing exclusively on the phone.

Today, this sounds ordinary. In 2002, it was a significant departure from how most mobile devices worked.

The architecture allowed Sidekick users to access online services without managing complicated synchronization software. It also supported an application catalog, providing a relatively simple way to add functionality to the device.

In many ways, the Sidekick anticipated the connected smartphone ecosystem that Apple and Google would later popularize. Long before cloud storage became a standard feature of mobile phones, Danger had built a system that automatically synchronized contacts, calendars, messages, and other personal information with remote servers. Users could lose or replace their phones and recover much of their data simply by signing into their accounts. The Sidekick also offered downloadable applications, instant messaging, web browsing, and email in a single device, years before the modern smartphone became commonplace.

But there was a catch. Unlike phones that stored most personal information locally, the Sidekick depended heavily on Danger’s servers to manage and preserve user data. This made the device remarkably convenient when everything worked, but it also meant that users had limited control over their own information. A problem with the central servers could affect thousands of customers at once, regardless of whether their individual phones were working properly.

That weakness became painfully clear in October 2009, when a major server failure left T-Mobile Sidekick customers unable to access personal information stored in the cloud. Microsoft, which had acquired Danger in 2008 for a reported $500 million, initially warned that contacts, calendar entries, photographs, and other data might have been permanently lost. The incident quickly became a public relations disaster for both Microsoft and T-Mobile, particularly because the Sidekick had been marketed around the convenience of keeping personal information synchronized and protected.

Microsoft eventually recovered most of the affected data, but the damage to the Sidekick’s reputation was considerable. The outage showed that cloud storage was only as reliable as the systems maintaining it. It also exposed the risks of placing essential personal information in the hands of a single service provider without adequate backup and recovery procedures.

The irony was that the Sidekick had helped establish many of the features that would define the next generation of smartphones. Its dependence on centralized services was not fundamentally different from the direction Apple and Google would take with their own mobile platforms. The difference was that those companies would build much larger ecosystems around their devices, with more developed systems for storing, synchronizing, and recovering user information. The Sidekick had demonstrated the appeal of a constantly connected phone, but the 2009 outage also showed what could happen when the infrastructure behind that connection failed.

The Last Sidekick

T-Mobile stopped selling the original Danger-based Sidekick models in 2010.

The following year, the company attempted to revive the brand with the Sidekick 4G, manufactured by Samsung.

The new phone ran Android rather than Danger’s original operating system. It featured a 3.5-inch touchscreen, a five-row physical keyboard, and a new pop-tilt mechanism that paid tribute to the rotating displays of earlier Sidekicks.

It was a reasonable attempt to combine the Sidekick’s identity with a modern smartphone platform.

But the market had moved on. Touchscreen smartphones were becoming the default, and the physical keyboards that had once made the Sidekick so appealing were increasingly viewed as unnecessary.

On May 31, 2011, the original Danger online services shut down, marking the end of the platform that had powered the Sidekick for nearly a decade.

The Samsung Sidekick 4G would be the last conventional smartphone to carry the name.

Why the Sidekick Still Matters

The Sidekick occupies an unusual place in technology history. It wasn’t the first smartphone, and it certainly wasn’t the most powerful. Its cameras were primitive, its internet connections were slow, and its software eventually became outdated.

But it understood something about mobile computing before much of the industry did: people wanted to be connected to their friends all the time.

The Sidekick made that possible through a combination of hardware, software, and online services that felt remarkably cohesive for its era.

It also made smartphones fun. The rotating screen, colorful designs, physical keyboard, and emphasis on instant messaging gave the device a personality that is largely absent from modern phones. Today’s smartphones are vastly more capable, but they are also remarkably similar. Most are thin slabs with large touchscreens and nearly identical interfaces.

The Sidekick came from a period when manufacturers were still experimenting with what a connected mobile device should look like. There is a reason people still remember the satisfying movement of its screen, the feel of its keyboard, and the experience of chatting with friends on AIM.

The Sidekick wasn’t simply a phone that happened to have internet access. It was an early example of what would happen when the internet became something people carried everywhere.

And for a few years, it made that future look pretty cool.

There was a time when watching your television somewhere other than your house was a fairly radical idea. Before Netflix became a streaming service, before the iPhone, and years before every television network had its own app, three guys came up with a fairly straightforward solution: take whatever was playing on your television at home and send it over the Internet.

That idea became the Slingbox, one of those strange pieces of transitional technology that makes much more sense when you remember the problem it was designed to solve. In 2005, television was still attached to a place. You could have hundreds of cable channels, a TiVo full of recorded shows and a fast Internet connection, but the moment you left your house, most of that entertainment stayed behind.

The Slingbox changed that by putting your own television connection online. You plugged the box into your cable or satellite receiver and your home network, and it encoded the video so you could watch it remotely using SlingPlayer software. An infrared blaster even controlled the cable box, meaning you could sit in a hotel room in another state, change the channel on your laptop and watch the physical cable box sitting back in your living room respond.

Sling Media called the idea “placeshifting,” a play on the “timeshifting” that TiVo had popularized. TiVo let you separate a television program from the time it aired. Slingbox separated it from the place where your cable company expected you to watch it. Twenty years later, that sounds completely normal. In 2005, it was weird enough that Sling needed a new word to explain what the box did.

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In February 2006, Steve Jobs took the stage at Apple and announced that the company was about to reinvent the home stereo.

During his presentation, he talked about the iPod. By 2006, iPods were a huge business. Apple was making $8 billion a year on the devices, and it was selling millions a quarter. This meant they were everywhere. People were carrying them on the train. The ubiquitous white earbuds were visible in bank lines and on city streets. We were connecting them to our cars and stashing them in our pockets. Apple also allowed for a constellation of hardware makers to build docks for the iPod. And Steve Jobs didn’t like that so well.

He wanted something better. He wanted to show the world something new.

What he gave us was a large white box with an iPod sticking out of the top.

What he gave us was the iPod Hi-Fi.

The iPod Hi-Fi was Apple’s attempt to take the iPod out of your pocket and make it the center of your living room. Apple called it a “high-fidelity speaker system,” and Jobs said it offered “true high-fidelity sound quality” from a single enclosure. At $349, Apple was not treating it like another little iPod dock. This was supposed to replace a stereo.

It was also, in several ways, a very good product.

Inside the 17-inch-wide enclosure were two 80mm wide-range drivers and a 130mm woofer. There was an integrated 30-pin iPod dock, an Apple Remote, touch-sensitive volume controls, and an auxiliary input that accepted both analog and optical digital audio. It charged your iPod, and you could even load the Hi-Fi with six D-cell batteries and carry the whole thing somewhere like a sexy, sleek boombox.

The design was pure mid-2000s Apple. It was made of white plastic with a black removable grille, almost no visible controls, and very little setup. There wasn’t even a power brick hanging behind it because Apple built the power supply into the enclosure.

And contrary to the reputation it later acquired, the iPod Hi-Fi actually sounded pretty good.

Ars Technica tested it against the Altec Lansing inMotion iM7 and Klipsch iFi, two serious competitors of the period. The reviewer came away surprised by the Apple system, writing that it produced a full sound, managed respectable stereo separation for a single-box system, and measured with the flattest frequency response of the three systems tested. There were complaints about somewhat muddy vocals and uneven bass in certain situations, but the basic verdict was clear: this thing could play music.

The one thing that happened during this time was the hemming and hawing by reviewers. People who got the Hi-Fi to test loved it. They could easily ignore the $350 price tag and the device looked decidedly futuristic. Just look at ti compared to the wonky, Wired-circa-1998 aesthetic of the Xbox.

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Steve Jobs was pissed.

He stalked the stage like a tiger. He was angry. You could tell he hated this “One more thing” moment.

This wasn’t the product he wanted to be showing, let alone holding in his hand.

“There’s one more thing about iTunes that we’re announcing today. You’ve probably heard about this,” he said. He was angry at his team. Product news had leaked like a sieve, and anticipation for the phone was high. The tech press was in a tizzy, imagining a phone that was either better than an iPod or, as we read in this 2005 Forbes article, a dud:

For more than a year, Apple and Motorola’s plans to release an iTunes-enabled phone have tantalized the music and mobile phone businesses. Now, with the two companies set to unveil the long-rumored handset Sept. 7, they might be underdelivering.

A person who has seen a version of the phone says it was designed to accommodate just 25 songs, which would be “sideloaded” from a user’s computer using iTunes. The phone was equipped with a 128-megabyte Sandisk TransFlash memory card—just one-quarter the capacity of Apple’s smallest iPod, the 512-megabyte shuffle, which holds about 120 songs.

The product, even in rumorville, sounded like garbage. Hilariously, the tech press thought this mock-up by an LSD-addled design undergrad was going to be the real deal.

Meanwhile, Apple was ruling the world. Their products were flying off the shelves, iPods were status symbols, and Macs were popular again. Jobs didn’t need to do this, and he clearly didn’t want to.

So there he was, faced with releasing a phone with a partner that he would consider inferior at best and shitty at worst. But he kept slogging through.

“Today, we are introducing the iTunes phone. This is a phone that we have worked on with Motorola that has an iTunes client in it where you can play iTunes music that you’ve gotten from your CD library or bought from the online store right on your phone,” he said. Listen to his language. “We worked on it with Motorola,” he said. He didn’t build it. Apple didn’t have a hand in the hardware. They put an iTunes client on it. Back in those heady days of Apple, everything was a premium walled garden. You could have an amazing interface, great design, and solid tech, or you could have, well, a Motorola. And he underscored that multiple times.

“The phone is made by Motorola. We have designed the iTunes client and work with them to integrate it into the phone. It’s called a Motorola ROKR. And it’s a pretty cool phone,” he said using language we’d normally reserve for a toddler we don’t know showing us a particularly colorful booger. “It’s a quad-band GSM phone. It’s got a built-in camera, built-in stereo speakers that are quite good actually. Stereo headphones with a headset on them as well.”

I’d go on, but it’s not worth it.

Long before the iPhone put a computer, camera, music player, and phone into one little slab, there was the Motorola ROKR E1. And it was the biggest hunk of crap ever announced at an Apple keynote.

But if it hadn’t been for the ROKR, we’d never have the iPhone.

ROK down to E1 avenue

The Motorola ROKR E1 was the first mobile phone to feature official iTunes support, combining Motorola’s E398-based candybar design with Apple’s music software. It was clad in a pearly off-white and orange. It had none of Apple’s design language except for a nod to iTunes in the interface.

The phone featured a 262,000-color display, a dedicated iTunes button, and a joystick for browsing music by song, artist, album, genre, or playlist. It supported MP3, WAV, and AAC files, including DRM-protected tracks purchased through the iTunes Music Store, as well as album artwork, playlists, shuffle playback, podcast bookmarks, and song ratings. Music had to be transferred from a Mac or PC rather than downloaded directly to the phone, with transfers handled over the relatively slow USB 1.1 connection. The ROKR also included side-mounted lights that could flash and vibrate in time with music. And it had “quite good” speakers.

Apple, Motorola, and Cingular pitched it as a way to take your iTunes library out of your computer and put it directly onto your phone. Steve Jobs called it, in effect, an iPod shuffle built into a phone.

It was also kind of terrible.

The ROKR came from a very different period in mobile technology. Phones were becoming cameras, music players, email devices, and tiny web browsers, but nobody had quite figured out how all of those things were supposed to fit together. The ROKR represents one of the strangest attempts.

Consider the interface. The phone had a full set of regular features — a calendar, an address book, and a bit of email and web. It also had that iTunes icon and the iTunes button. Both look like they were slapped on by committee, some lazy exec saying “Make it easy to see but don’t remove the garish Cingular and Motorola logos.”

In other words, iTunes was an afterthought in an era when it “Rip. Mix. Burn.” was the battle cry for turn-of-the-century music lovers. At a time when people were carrying hundreds of songs on their iPods, the ROKR was simply silly.

Physically, it wasn’t particularly new. Motorola essentially took the existing E398 candy-bar phone, gave it a white-and-silver finish, and added Apple’s music software. It had a 176 x 220 color screen, a VGA camera, Bluetooth, stereo speakers, and a 512MB TransFlash memory card. It cost $249.99 with a two-year Cingular contract.

Further, the ROKR was one of the first devices to support iTunes loading. Plug the ROKR into your Mac or PC and it showed up in iTunes. You could move purchased music, ripped CDs, podcasts, and audiobooks onto the phone. Album artwork appeared on the tiny screen. When somebody called, your music paused so you could answer.

There was just one ridiculous problem.

You could only carry 100 songs.

Not 100 albums. Not as many songs as would fit on the memory card. Exactly 100 songs.

Even if you installed a larger memory card, the iTunes software wouldn’t play song number 101. The restriction was especially odd because Motorola’s separate music player could play additional MP3 files stored on the card.

Then there was the transfer speed.

The ROKR used a painfully slow USB connection for loading music. Engadget reported that transferring 100 songs took about 42 minutes. There was no iTunes music transfer over Bluetooth and no way to buy songs directly from the phone. You bought or ripped music on your computer, plugged in the ROKR, and waited.

This was particularly strange because Apple introduced the iPod nano at the same event.

The nano was thinner, prettier, and could hold as many as 1,000 songs. So Apple effectively introduced its first iTunes phone and then immediately showed everyone a much better way to carry music.

Reviewers noticed. TechRadar complained about the 100-song limit, slow transfers, and inability to download music over the air. Engadget found the interface sluggish. Stuff later described the ROKR as feeling like an experimental side project rather than a serious Apple product.

But that’s what makes the ROKR interesting today. The ROKR arrived near the end of an era when phones were still sold largely on hardware design rather than a unified software experience. The constellation of devices produced by Samsung, LG, and Nokia at that time were differentiated not by features but by design. The Nokia 8210 was interesting because it was tiny. The Nokia 8110 had a slide out key cover. The Motorola 120t looked like a bar of soap. There weren’t any special features and each model was approximately the same. Adding iTunes to the ROKR made Motorola stand out, even though they didn’t know how to market the product.

There was also this:

But the ROKRy showed Jobs that people didn’t want to carry a phone and a separate music player forever. Their music library would eventually live on the same device they used for calls, messages, photos, email, and the web. The ROKR tried to make that happen while the old mobile-phone business was still focused on the phone versus the software.

The ROKR was widely regarded as a flop. Apple wanted out.

TechEBlog writes:

Behind the scenes, the ROKR E1 was a learning curve for Apple. Teaming up with Motorola and Cingular was a bumpy ride, exposing the headaches of split design duties. Apple poured its energy into the iTunes software, while Motorola’s hardware gave the phone a clunky, un-Apple vibe. Clashes over song limits, branding, and looks—some called the prototype “ugly”—dogged the project, with Steve Jobs himself labeling it an “experiment,” per Jon Rubinstein, then iPod division chief. This stumble convinced Apple to seize total control, birthing the iPhone, and by September 2006, the ROKR was dropped as Apple chased its own vision.

Less than two years later, Apple introduced the iPhone. The ROKR showed Apple what it didn’t want, and it energized Jobs. Even as smartphones entered the market, he ridiculed them for having styluses and cheap screens. He didn’t like plastic because of the ROKR, so the first iPhone was made of metal. He hated phone interfaces, so he forced his engineers to build skeuomorphic representations of reality that allowed the screens to “rubber band” when you pulled down on lists and date pickers to feel like physical dials. To zoom you pinched with two fingers instead of tapping on an ugly joystick.

Further there was no 100-song limit, no Motorola interface surrounding Apple’s software, and no need to bolt iTunes onto somebody else’s handset.

The ROKR became a technological dead end almost immediately.

But sometimes dead ends are the most interesting gadgets to collect. The ROKR captures a brief moment when Apple knew the phone was going to swallow the iPod, Motorola knew music was going to matter, and neither company quite knew what the resulting device should look like.

The answer wasn’t the ROKR. But for a few months in 2005, this funny little Motorola was the closest thing we had to the future.

In the mid-2000s, MIT professor Nicholas Negroponte had a wild idea: what if every child in the developing world had a computer? And this wasn’t some smoky gaming cafe or a school computer. It was a machine that the child owned and could use every day. I twas connected to the nascent internet, had a simple operating system, and was rugged enough to survive any conditions.

The result was the One Laptop per Child project and one of the strangest, most ambitious computers ever put into mass production: the OLPC XO-1.

Most people knew it by another name: the $100 laptop.

Launched in 2007, it never really became a $100 laptop. It didn’t transform global education in quite the way its creators expected, either. But the XO still mattered. More than 2.4 million had shipped by 2011, according to the Computer History Museum, and some estimates eventually put total distribution around 3 million machines. More importantly, the project forced the computer industry to reconsider some basic assumptions about what a laptop needed to be.

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In January 2003, a little-known Florida company called Infinium Labs announced that it was going to take on Sony, Microsoft, and Nintendo.

The idea was ludicrous: to inject a new console into the gaming world without a single major partner, a nebulous marketing plan, and shady founders. After all, the Xbox and PlayStation franchises were running on all cylinders while Nintendo had just launched the Game Boy Advance SP to much acclaim. But there was a strange itch in the gaming world, however, one focused on bringing PC games to consoles, something that only a few companies had tried before.

This new machine was called the Phantom and it would prove to be one of the most beguiling and, more importantly, ridiculous stories in modern gaming.

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Bloop! Bloop!

You remember the sound. It was a cross between a bubble popping and a robot burping, a noise that meant you were about to watch The Daily Show, even if it had aired the night before. It wasn’t live, but it didn’t matter. You had a TiVo.

Today, that seems almost ordinary. Every streaming service remembers where you stopped watching. Every phone can record video. Every television comes with apps. But in 1999, TiVo felt like science fiction.

Before TiVo, television followed a schedule. If your favourite show aired at 9 p.m., you were in front of the television at 9 p.m. If you missed it, you hoped for a rerun. Some people programmed VCRs, but most people remember that experience as a collection of blinking clocks, confusing menus, and tapes that somehow always ended before the final scene. You knew that time mattered, and if there were commercials, you had to sit through them or go grab a sandwich.

I still remember the terrible days before TiVo. We would watch prestige TV — Grey’s Anatomy or The Sopranos — and have to sit still. Nobody was on their phone. Nobody was half watching, half browsing TikTok. Hell, TikTok didn’t exist. Instead, you were glued to the set at a set time and didn’t get to leave until the show was over. It was torture.

TiVo changed that relationship completely. Television stopped being something broadcasters controlled and became something you controlled.

The box, devoid of buttons, sat quietly beneath your television, recording hours of programming onto a hard drive. You could pause live television, rewind a scene you had just missed, or skip commercials with a few taps of the remote. Those features sound ordinary now because they became the standard. At the time, they felt almost magical. You had a collection of shows you could keep forever. There was that one episode of Friends you liked. Or that documentary that you were going to pop back into. It was right there, waiting on a spinning hard drive.

TiVo also did something even more interesting. It learned what you liked. If you watched enough documentaries or late-night comedy, it would quietly record similar programmes it thought you might enjoy. Long before Spotify playlists and Netflix recommendations, TiVo was already trying to answer a simple question: “What should I watch next?”

The TiVo knew. But how?

The TiVo story

There are only a few examples today of what TiVo meant to the culture at large. Google took over search, and billions of people knew the verb. OpenAI has far fewer users and is barely a blip in the zeitgeist. But to TiVo… to perform the act of TiVoing? That was something special and rarified and global.

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Long before the Amazon Echo Show, Google Nest Hub, or even the iPad, there was the Chumby.

Released in 2008, the $200 Chumby was a strange little Linux computer wrapped in soft leather with a 3.5-inch, 320×240-pixel touchscreen, stereo speakers, Wi-Fi, and an accelerometer. It sat on your bedside table or kitchen counter and displayed clocks, weather, RSS feeds, news headlines, Flickr photos, podcasts, Internet radio, stock prices, and thousands of other widgets. It was always on, always connected, and always updating.

In 2008, a device like the Chumby felt like the future. Devices like One Laptop Per Child were turning towards a softer, kinder design language that was echoed by the early iMac. Gone were hard lines and blue LEDs, replaced by pleather and cute little squids.

I remember seeing Chumby for the first time, probably at CES, and thinking that I wanted one. The idea of an always-on device that just sat there was quite tantalizing, and there weren’t enough DIY tools available to make something like the e-ink weather display that sat on my desk for years until the Raspberry Pi that powered it burned out.

The Chumby’s original creator, Andrew “bunnie” Huang, launched the product at Foo Camp in 2006. The original product reached developers who were tasked with building apps for the device. The company launched in San Diego and, amazingly, raised $5 million from OATV, Avalon Ventures, and Masthead Venture Partners in December 2006. Steve Tomlin worked with Huang to bring Chumby Industries to life.

Although the Chumby looked like a plush toy, it was anything but. The Chumby ran Linux, its hardware designs were open to developers, and owners were encouraged to modify both the software and the electronics. It became a favourite among hackers because it was easy to customise. It was a definite predecessor to smart displays from Google and Amazon, but there was one important difference: the Chumby was open and ostensibly offered an opportunity for developers to create apps for the little device — something the then-nascent iPhone decidedly didn’t let you do.

Plus, it was cute. Julie Strietelmeier (whose photos I stole because all the posts I wrote about the Chumby on TechCrunch are gone) of the Gadgeteer wrote: “As an internet device, the Chumby is a lot of fun. Sure, you can access all the same information on your regular computer, but you would need to manually go to each site to get the info. With this device, the info comes to you.”

Another interesting aspect of the Chumby launch was their Chumblog, a very detailed WordPress blog about the Chumby and announcing all the various changes to the platform over the years. This was probably one of the most visible and interesting examples of “building in public” I’ve ever seen.

The idea behind the device was simple. Instead of sitting down at a computer to check the weather or read the news, the Internet should quietly exist around you. The Chumby was designed to surface useful information at a glance, making it one of the earliest examples of what we would now call ambient computing.

Chumby came at an interesting time in the tech ecosystem. The iPhone was the ultimate closed device, and app stores were just taking off on other platforms. The idea of an always-connected smart home device was difficult to imagine, but manufacturers like Samsung and Sony were promising instant handoff from your phone to your TV to your fridge, with devices sensing where you were and turning on as needed.

The Chumby was supposed to be the window into that smart home brain, a way to interact with all the devices on your brand-new Wi-Fi network. It’s hard to imagine now, but we were not as inundated with screens back in 2008, and adding another one, even a chintzy 320×240-pixel one, seemed like the future.

What happened to Chumby?

The company launched the $100 Chumby One in 2009, a plastic version of the Chumby hardware that was easier to mass-produce. They went on to launch a few more models and kept the servers running until about 2012. The blog was updated as late as December 2014.

Chumby’s problem was timing. Smartphones quickly became the place where people checked news, social media, and weather. For many owners, the devices stopped working when the company’s servers disappeared, although an enthusiastic community later kept the platform alive with open-source firmware and subscription services. The Chumby was simply too underpowered to withstand the onslaught of DIY gear that was coming out, including the aforementioned Raspberry Pi and Arduino devices that could do everything Chumby could do.

Chumby was an odd evolutionary turn-off from the jungle of always-on devices that now rule our lives. It was soft, cute, and silly, something gadgets rarely are.

Looking back today, the Chumby feels less like a failed gadget and more like a glimpse of the future. It predicted smart displays, connected homes, open hardware, and the idea that useful information should simply appear when you need it. It arrived years before the world was ready and showed the world the softer side of the Web, something that is absolutely missing for us all right now.