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Hot To Trot: The new Hotmail gives Gmail a run for its money.

Hotmail is old. Really old. When Hotmail launched in the summer of 1996 as the first free e-mail system available to everyone, Bill Clinton was running for re-election, the economy was booming, and Lady Gaga, known to her classmates as Stefani Germanotta, had just turned 10. Much of the world wasn't online; indeed, the idea of being "online," or of the Internet as a place where we'd soon do much of our shopping and socializing, seemed fantastical. The very prospect of getting mail on your computer struck people as revolutionary. You mean anyone, anywhere, could send you a message? For free? And it would get there instantly? Crazy!

Hotmail was an instant hit—within a year and a half, it had attracted nearly 9 million users. That was a substantial portion of the Internet's population—AOL, the largest ISP, also had 9 million subscribers at the time. Hotmail's success inspired a wave of copycats. AOL, Yahoo, and various now-defunct sites launched their own free e-mail systems.

In late 1997, Microsoft bought Hotmail and folded it into MSN. And that seems to be where history stops for Hotmail. The service continued to pick up millions of users—it's now the world's largest free e-mail system with more than 360 million users around the world. (Yahoo has more than 300 million and Gmail a little less than 200 million, according to comScore.) But even though it's grown substantially since its early days, Hotmail hasn't done much to distinguish itself. It's long been seen as an e-mail service for people who still use the Web as if it's 1996—those who don't get a lot of e-mail, who don't care much about speed or storage space, and who aren't itching to use smartphones or iPads. Hotmail, in other words, is an old service for old people, and if you're still sending messages from a Hotmail account, you might as well be e-mailing from the past.

Microsoft wants to change that perception. Sometime this summer, it will roll out a fantastic new upgrade of Hotmail. I've been using a pre-release version of the service for a couple of weeks now, and I'm a huge fan. The new Hotmail is fast, well-designed, and adds a host of features that bring it up to par with other e-mail services, including Gmail. Indeed, it has several features that I wish Gmail included. I'm not switching over yet—I've got six years' of archived mail in Gmail, and I still consider it the best e-mail system on the planet. But that may be just a matter of taste and familiarity. I consider the new Hotmail a very close second, but the more I use it, the more I like it—and I bet loads of people will believe the new version surpasses every other e-mail system around.

Gmail won my heart because it seemed to be designed for power e-mailers—people who get hundreds of messages a day, who use a range of devices to check their messages, and who need (or want) to keep all their e-mail forever. To win that audience, Gmail broke with the past. Not only did it look radically different from other Web e-mail clients; it instituted a range of features—conversation view, "labels" instead of folders, the idea of "archiving" mail instead of deleting it—that diverged widely from the older style of e-mail. The beauty of the new Hotmail is that it's an old-timey, friendly e-mail system with power features. I think advanced users will like it just fine, but its chief audience will probably be the hundreds of millions of people who want more from their e-mail without having to learn an entirely new e-mail philosophy.

The new Hotmail thus looks pretty similar to every other e-mail system you've ever used: Your mail folders are listed on the left side of the screen, and the contents of each folder are displayed in a large well in the center. By default, messages are shown singly—that is, each distinct e-mail occupies its own line in your inbox. But Hotmail has an option to impose a Gmail-like conversation view, which will collect a thread of e-mails with the same subject line into a single box. Hotmail also has an optional preview pane, which lets you see each message below your inbox—not a novel feature in e-mail, of course, but one that isn't available in Gmail. I suggest turning on both of those options.