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The Modern Smartphone Started as a Sidekick

This pre-smartphone device had its moment in the limelight and became a fun gadget and a fashion statement. But it wasn’t able to compete with other smartphones, and by the time Paris Hilton left the headlines, the Sidekick was old news too.

But the Sidekick was more than just a status symbol — it was actually a trailblazing piece of technology. It proved phones could do more than just make calls while being sexy and fun. Despite this, it’s become a relic of the past and failed to have the longevity of its rivals.

What was the Sidekick?

To understand the intentions of this device, it may be easier to look at its original name: the Hiptop. Danger, the device’s designer, wanted to offer the experience of a laptop, but make it portable enough that it could be carried on a belt clip (because that was a popular way to carry bulky phones in 2002).

And to Danger’s credit, it was a successful endeavor. The original Hiptop could take calls, send e-mails and texts, and connect to instant messaging services — but none of that was as impressive as its ability to connect to the internet. Even in 2002, the phone could get online, though it was a slow service on a black-and-white screen. But it actually worked, and in the US, it was sold by T-Mobile and branded as the Sidekick.

Unlike the iPhone, the Sidekick bragged about its full keyboard and analog buttons. It was supposed to be easy to use and people understood these features. But the real head turner was the screen that swiveled into place and revealed a QWERTY keyboard. Not only was it functional, but in the words of Paris Hilton, that’s hot.

The Sidekick Gets Famous :

The Sidekick wasn’t really meant for businesspeople. It was meant for people who were always connected, so it had to play the roll by looking cool. But it also came with a price tag: $40 for unlimited data in the US. This gave it a higher barrier to entry than other phones of the early 00s, but not so high that no one could buy it.

In 2003, T-Mobile gave the Sidekick a color screen, but the phone really entered the pop culture zeitgeist during its second iteration: the Sidekick II. This device was slightly slimmer and had a built-in camera, but T-Mobile wasn’t just trying to push technology forward; the company was trying to make it cool.

Just look at the advertisements. The original Sidekick had an informative, cartoony commercial. The Sidekick II swapped the sketches for stars and lined ads with celebrities like Snoop Dogg, Paris Hilton, and Tony Hawk. And it’s hard to deny this plan worked. If you know the Sidekick, it’s probably because you saw it in the hands of Paris Hilton, Lindsay Lohan, or Kim Kardashian.

Of course, these people lived in the headlines and drove culture during the decade, but they also weren’t known for their intelligence. This is what the Sidekick got right — and the reason it broke boundaries that held the Blackberry back. It was easy to use, and you didn’t need to be a tech guru to understand the features.

People were so quick to adapt to the phone that the Sidekick II transcended the tech bubble and became fashionable. Users could customize their phone with bumpers along the edge, and by 2005 — in a move that could only be taken seriously in the mid-00s — T-Mobile partnered with Juicy Couture and Mister Cartoon to release custom devices.

That level of popularity got a lot of eyes on the Sidekick II, but this could have been the beginning of the end.

The End of the Sidekick

As the Sidekick was becoming the it accessory, celebrities were given reason to swivel their screens shut. Paris Hilton’s Sidekick was hacked in 2005, leaking her conversations, address book, and some R-rated photos. And apparently, getting information from T-Mobile wasn’t that hard. Security had been an issue for T-Mobile (and it continues to be), and this caused a few eyebrows to raise.

But the only person with Paris Hilton’s status is Paris herself — so most people weren’t afraid of T-Mobile’s security, they were afraid of T-Mobile. In 2022, T-Mobile makes a big deal about having the largest 5G Network, and there’s a reason the company’s obsessed with discussing its coverage. In its earlier days, it was known for having budget coverage for a budget price, especially outside of urban areas. But the Sidekick came with an additional service plan, mitigating the appeal of the lower price tag.

T-Mobile wanted to keep the momentum going, so the Sidekick 3 was introduced in 2006. This included MP3 support — because people had separate MP3 players back then — and it was clear the Sidekick understood an all-in-one portable device needed to include the tune. Of course, other brands knew this too, and the first iPhone was released at the beginning of 2007.

The iPhone certainly changed the smartphone industry, but it wasn’t going to kill the Sidekick right away. At first, the iPhone was only available on Cingular (it wasn’t on T-Mobile until 2013), and Danger released a budget-friendly Sidekick in 2007. When people were ready to get their first smartphones, T-Mobile would be ready, but someone else had their eye on the Sidekick.

In 2008, Microsoft bought Danger and therefore the Sidekick. In a world where people were Macs or PCs, Microsoft brought the smartphone the uncool side. Plus, the Sidekick lost its swivel with the Sidekick Slide, and it was blending into the pack of generic cell phones. Then, in 2009, Microsoft’s server crashed and lost a lot of user data. This was a bad look for the struggling smartphone, and by 2011 Sidekick’s servers shut down.

While a Sidekick 4G was released in 2011, it ran on Android software and was essentially a reboot of the device. According to some people, the Sidekick was the first smartphone to die.

How the Sidekick Changed Technology

If the Sidekick never existed, would smartphones still be the necessity they are today? Yes. Would the iPhone look any different? No. So it’s easy to overlook its impact, but there’s a reason people associate the Sidekick with the early 2000s.

It represented the direction culture was moving — always connected and replacing individual devices with an all-in-one. Starting with the Sidekick II, the device had the power to serve as a digital camera and replace functionalities once reserved for the computer. It demonstrated that, if given the option, people would rather avoid talking on the phone. All of the texting, emailing, and instant messaging made those data plans worth their cost.

But most importantly, it looked cool. If you made a phone that looked like the Sidekick today, people would still turn heads. Before the iPhone told us what a smartphone should look like, PDAs and personal media devices all looked very different. The Sidekick understood that this was a new market, and many people were unfamiliar with these pre-smartphone devices. So Danger loosely modeled it after the laptops of the time, making it easy enough to understand, but not so clunky that it could look out of place while being used at the club.

Sidekicks were cool and trendy, but they weren’t must-have technology. In many ways, it was ahead of its time. It loaded full websites —because the mobile versions of the era weren’t usable — and the keyboard was easy to understand, but it was limited. The existence of the Sidekick started to highlight the areas where smartphones would need to improve before the general public really started to adopt the technology.

In the end, the Sidekick couldn’t compete with the budding smartphone markets, and it got choked out by brands like Apple and Droid. But anyone that had a Sidekick knows how innovative it was. It made users feel like technology was changing, yet its usability felt familiar. Perhaps this is why T-Mobile tried to bring it back with the Android-based “Sidekick 4G.” Of course, this didn’t work. This phone was meant to trailblaze and swivel, and a device that conforms to current smartphone standards doesn’t understand the importance of the Sidekick.

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The Modern Smartphone Started as a Sidekick

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