The Sidekick iD, a smaller and more affordable version of the 3, dropped in April 2007. To keep the price at a low $99, Sharp (the Sidekick’s manufacturer) removed a memory slot, Bluetooth features, and a 1.3-megapixel camera. The Sidekick LX was released the following October, the first Sidekick to be launched after the iPhone’s introduction in June of that year. While the keyboard and colorful display was praised, the phone’s large size and slow web-browsing speeds kept it from keeping up with the iPhone and BlackBerry Curve.

Microsoft bought Danger Inc. in Sept. 2008 for $500 million and had to steer the Sidekick brand through its second scandal.

In Oct. 2009, Microsoft was hit with a legendary outage that kept users from accessing their pictures, contacts, and other data. It wasn’t just a measly hour of downtime or anything like that: The outage lasted for almost a week, and some data didn’t return to users until late November. Celebrities who backed the phone soon turned against it. Users hit Microsoft with lawsuits for not having a backup plan for the outage—some cases weren’t settled until 2011. ​

The following year, with consumers throwing their cash toward the iPhone and Samsung Galaxy smartphones, Microsoft attempted to tap into the youth market the same way the Sidekick had a decade earlier. It released the Kin, a miniature Sidekick-inspired smartphone with a sliding keyboard that was tailored for teens who liked Facebook and Twitter. Two months after its release, it was discontinued. Smartphones like the iPhone were the new status symbols, and keyboards weren’t cool. Just ask Blackberry.

Devices that sold themselves on large keyboards soon gave way to phones with touchscreens and as many buttons as you have fingers on one hand. As the physical keyboard became less useful, the Sidekick brand went through its biggest change in 2010: T-Mobile announced that it was dropping Danger’s data service. So, Danger turned off its servers, and older Sidekicks that relied on their data centers were rendered useless. Then, Microsoft hit the reset button: All future Sidekicks were to run on Google’s Android OS, the same software that Sidekick co-founder Andy Rubin had developed. Things seemed to have come full circle, but not in a good way—this was the end of the line. Samsung’s Android-powered Sidekick 4G—released in April 2011—was the final Sidekick to leave factories before its discontinuation.

The Sidekick succeeded because it showed consumers how cool technology could be, that they could personalize a chunk of plastic and chips to make it their own, and ushered in an era of mobile computing for the masses. Say what you will about how fast its rising star burnt out, but the Sidekick is an important element in the link between cell phone and smartphone, technology and style.

What Danger and T-Mobile were able to do (whether it was intentional or not) was tap into something that Dr. Dre and Jimmy Iovine later did with their Beats headphones (and what Apple is attempting to do with the Apple Watch today) by making a device that's essential to one's personality and status, something stylish for the coming generation of consumers. The Sidekick wasn’t ever going to be able to compete with the likes of the iPhone and Samsung Galaxy, unless it morphed it something else entirely, but its features foreshadowed what was on the horizon. So many of us wanted an iPhone before we knew we wanted one because we saw the future of connectivity in the Sidekick.

In an era where new pieces of technology become obsolete by their first birthday, the Sidekick is, well, very much obsolete, but it has kept a lasting coolness about it that devices today lack. In the evolution of the mobile phone, the Sidekick has an important place (both in marketing and technology) in helping jumpstart the modern smartphone craze that would go into full effect at the end of the 2000s.

The device can still evoke nostalgia for those who owned one not only for its Internet capabilities, but for it being a pocket-sized canvas of expression during that slice of our lives when we were still coming into our own, whether it was decorating it with our high school colors, sticking our favorite team’s logo on it when they won the championship, or downloading the newest Jay Z track and making it our ringtone. While we grew, the technology grew with us. The Sidekick is very much a representation of the time and place in which it was popular. While whatever surviving Sidekicks left may be packed away somewhere in the garage, whenever one is rediscovered, we may look at it in the same fondness as once-embarrassing prom photos and high school love letters, if even for a moment.

It was a toy for those who thought they had given them up long ago.