It was the late 90s and social media platforms like MySpace and Facebook didn’t yet exist. Texting was still in its infancy as very few people actually owned mobile phones at that point. E-mail was a popular method of communication among those with access to a computer, but it lacked the real-time feel that makes in-person conversation so appealing.

For that, you needed an instant messaging program, and when the mainstream Internet movement really started to take root, there were four major competitors jockeying for position: AOL Instant Messenger, ICQ, Yahoo! Messenger and Microsoft's MSN Messenger.

Microsoft’s entry launched on July 22, 1999, which was already late considering ICQ had been around for nearly three years and AOL had followed with AIM in the spring of 1997. Even Yahoo’s messaging client beat Microsoft’s to market by over a year, but as Microsoft proved, you don't have to be first to reach the top.

A key decision at the time was Microsoft's integration with Hotmail, leveraging the sheer popularity of the web email service owned by the company, to offer those millions of users the ability of instant communication.

Waging war with AOL

Version 1.0 of MSN Messenger Service shipped with a Spartan feature set including plain text messaging and a basic contact list. Right out of the gate, it caught the attention of rival AOL seeing as Microsoft had coded MSN Messenger Service to be able to chat with AIM account holders. Needless to say, AOL was not thrilled.

As former AOL engineer Eric Bosco recounts, any messenger service that connected to AIM’s network was required to provide a version type. Microsoft’s app identified as “MSN Messenger Version 1.0,” so Bosco and company tweaked AIM to cut the connection whenever this version tried to link up to its network.

Microsoft countered with an update that made MSN Messenger Service self-identify as AIM. AOL blocked it again, and this back-and-forth battle reportedly went on 21 more times before AOL threatened to inject malicious code into MSN’s network.

Microsoft backed off, and instead ended up partnering with another major player.

Onward and upward

Microsoft continued to build out its messaging client over the next several years, slowly but surely adding new UI elements and functionality like the ability to customize chat windows and facilitate file transfers between users. By early 2001, MSN Messenger Service had more than 29 million unique users worldwide, enough to make it the single most-used instant messaging service in the world according to Microsoft.

With the launch of Windows XP in 2001, Microsoft shortened the name of the program down to just MSN Messenger. A few years later, the Redmond-based tech giant reached an interoperability agreement with Yahoo! that would allow users of their respective IM services to chat with each other. Combined, it created the largest consumer IM community in the world with an estimated 275 million users.

From text-only conversations, to a whole world of interactivity, Messenger eventually gained features like smileys, webcam video conversations, sending short audio clips, playing games in real time with your contacts, and the infamous "nudge," which would send a buzzing sound and shake the chat window to get the attention of another user.

With the eighth major version launch of the program, Microsoft rebranded the app again, this time changing it to "Windows Live Messenger" to align with its broader Windows Live family of software and web services.

For a while, it seemed as though Microsoft could do no wrong with its instant messaging application. But as we all know, the best-laid plans of mice and men often go awry.

The beginning of the end

With the last several revisions of Windows Live Messenger, Microsoft stripped out a lot of core functionality, bugs in the platform were apparent, and even security was called into question over and over.

With version 9.0, for example, the company removed several default status options and eliminated the ability to adjust webcam settings during a video call. Windows Live Messenger 2009 RC saw Microsoft drop the custom sign-in sound feature.

Things went from bad to worse in 2012 when Microsoft forced Windows Vista and Windows 7 users to upgrade from an older version of the app to a newer release, and dropped support for Windows XP entirely shortly after. This was around the same time Microsoft acquired Skype.

The advent of social media and mobile devices couldn't be ignored either. These technologies were enabling new ways for people to stay in touch with friends and family that didn't involve a traditional computer.

Although Microsoft did release Windows Live mobile versions for several major platforms including iOS, BlackBerry, and Windows Phone (and even added integration with Facebook chat), there were a combination of factors that simply took Microsoft out of the IM game. Eventually, they found an exit strategy with Skype, but that didn't go so well either...

Along came Skype

In May 2011, Microsoft confirmed it would be buying telecommunications app Skype for $8.5 billion, and in November of the following year, we learned that Messenger would be rolled into Skype.

With the integration, Messenger users would still be able to contact their friends through Skype but it effectively set the wheels in motion to discontinue the standalone version of Windows Live Messenger. Furthermore, Skype was well liked and used on a global basis, but in Microsoft's hands, the development of the program did not flourish.

As sure as the wind blows, Microsoft started phasing out Windows Live Messenger in April 2013. China was the lone exception, but eventually, the app was pulled from this market as well on October 31, 2014.

If Microsoft could do things all over again, they'd probably not want to miss Windows becoming a major player in the mobile OS arena. In similar fashion, MSN Messenger could have been today's WhatsApp or Snapchat, but a lack of focus, the loss of trust from its immense user base, and a poorly managed transition to Skype landed Messenger in the technology graveyard.

MSN Messenger's influence persists in Skype and many of today's messaging platforms, but that’s another story for another time.

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The story of software apps and companies that at one point hit mainstream and were widely used, but are now gone. We cover the most prominent areas of their history, innovations, successes and controversies.