MSN was originally conceived as an online service provider in the vein of America Online, supplying local and proprietary content through an interface integrated into Windows 95's Windows Explorer.

The MSN group began life in the Advanced Technology Group, headed by Nathan Myhrvold and group was called AT-OLS (Advanced Technologies Online Systems group.

Following the rapid adoption of the Internet, partly fueled by the built-in IP protocol capabilities of Windows 95, the service was then rebranded as "MSN Classic" and a new incarnation was created, known as "MSN 2.0," which combined access to the Internet with web-based proprietary content in the new "MSN Program Viewer." The MSN Program Viewer was essentially an animated, stylized and streamlined interface on top of an Internet Explorer engine. When users logged in, they'd be presented with a several different "Channels" which were essentially categories for the various types of content available on MSN.

The Program Viewer was accompanied by MSN Quick Launch, which say in the Windows Notification Area. Both had menus that could be dynamically updated to guide users to content.

The new content made extensive use of multimedia and interactive features, including VBScript and early implementations of Macromedia Flash for animations. Interactive multimedia content was presented in a TV-like format, dubbed "MSN Shows." The many "shows" and content sites included an interactive online week nightly game show called "Netwits," a snarky site addressing women's issues called "UnderWire," and a regular celebrity interview and Web-surfing session called "One Click Away." These new destinations supplemented reinvented, Web-based, highly interactive of original MSN content such as CarPoint and Expedia.

While the "MSN Shows" approach was unique and innovative, the content wasn't easily accessible by users with low-end computers and slower dial-up connections (broadband Internet access hadn't yet hit the mainstream). The aggressive adoption of multimedia content during the late nineties proved to be ahead of its time, as the service was not as successful as hoped. After abandoning the "Shows" format, the service was again rebranded--this time as a more traditional Internet service in the MSN 2.5 release, with some exclusive content. The MSN Program Viewer was essentially abandoned in favor of defaulting users to the regular, more-featured Internet Explorer interface.

In 1999, the largely underutilized MSN.com domain was reinvented as both a Web portal and as a brand for a family of sites produced inside Microsoft's Interactive Media Group (IMG) and put MSN in direct competition with sites such as Yahoo!. Because the new format opened up MSN's content to the world, for free, the subscription service was rebranded MSN Internet Access.

The new MSN.com had a whole family of sites, including originals, content channels that were carried over from shows (although no shows remained), and new features were rapidly added. MSN.com also became a successor to the default Internet Explorer start page which, previous to MSN.com's reinvention, went to Microsoft Internet Home (a.k.a. home.microsoft.com, or, internally, "hmc").