Rocky. The Chicago Cubs. Charlie Brown. Avis, back when its whole schtick centered on being America’s #2 rental car company. America loves its underdogs–and the technology business has always been home to a disproportionate number of exceptionally lovable underdogs. They may never achieve market leadership, but without them, the tech in our lives would be less interesting, innovative, and inspiring.

So what is an underdog? Merriam-Webster says it’s a “loser or predicted loser in a struggle or contest” or a “a victim of injustice or persecution.” For this list, I’m using a somewhat different, tighter definition.An underdog, first of all, must be good–maybe better, in fact, than its more successful rivals. It should have a cult of intensely loyal fans. (Many of the products we’re about to discuss have fan bases that can be a little scary–you know who you are.) And it helps if it’s successful enough that it hangs around for awhile. (Some of the contenders we’re about to ponder have been underdogs for decades.)

Many tech underdogs end up triumphing, such as every behemoth of a corporation that  was founded in a garage or a dorm room—-Dell, Google, HP, Microsoft, and many others. You lose any claim on underdogship the moment you come to dominate your market. But I did include some items that started out dominant, and then were toppled by underdogs, thereby becoming underdogs themselves.

I considered dozens of contenders to come up with the twenty that made the cut for this article. I’ve ranked ’em in terms of overall significance. Take a gander–then tell me about the products, companies, and technologies that I should have mentioned but didn’t.

20. Quarterdeck DESQview

What it was: A DOS enhancement, released in 1985, that let you run multiple applications at once in movable, resizable onscreen windows.

Underdog to: Microsoft Windows, which debuted later the same year.

Notable virtues: It let typical PCs of the era multitask existing DOS apps quickly and reliably at a time when multitasking was a sexy new idea and Windows was still profoundly crude.

What made it an underdog: For one thing, it’s no great shock that Microsoft had an built-in advantage when it came to building multitasking interfaces on top of its own DOS. And compared to the fancy (for the 1980s) graphics sported by Windows, DESQview had a no-frills, text-oriented feel; that’s one of the things that its fans loved about it, but it also gave it less sizzle.

Random factoid: DESQview started as a clone of IBM’s TopView, an unsuccessful, even less flashy DOS multitasker.

19. Trackballs

What they are: A pointing device with a ball you spin with your fingertip–sort of the same idea as the original mechanical mouse, only upside-down.

Underdog to: Mice (with desktop PCs) and touchpads (with laptops).

Notable virtues: Trackballs make efficient use of desk space and are unbeatable for Missile Command. But as with all input devices, it’s mostly a matter of personal preference.

What makes them an underdog: Their brief moment of glory came in the early 1990s, when they were the dominant form of pointing device for notebooks–but they were soon nudged back into underdog status by touchpads. Other than that, they’ve a classic tech underdog: something that’s been passionately adopted by a really small group of people. (Including me: They’re my choice of pointing device for desktop PCs, and if Apple sold a MacBook with a trackball, I’d probably buy it.)

Random factoid: The first trackball was invented in 1952 by the Royal Canadian Navy, and used a…bowling ball.

18. ReplayTV

What it was: One of the first digital video recorders (DVRs) to bring truly simple, powerful recording of TV programs to consumers.

Underdog to: TiVo, which debuted more or less simultaneously in 1999.

Notable virtues: Excellent user interface; made it a cinch to skip commercials (one version even did it automatically); first version carried no monthly service charge.

What made it an underdog: That  original pricing model–you paid one flat fee for a box and lifetime service–made it a far costlier gizmo than TiVo, which subsidized the cost of the box but made you pay a monthly fee. Lack of an adorable mascot probably didn’t help, either.

Random factoid: Replay founder Anthony Wood later formed Roku, maker of a nifty video streaming device.

17. Digital Research GEM

What it was: A graphical environment, debuting in 1985, that provided a Mac-like windowing interface for DOS and the Atari ST.

Underdog to: Microsoft’s similar Windows, of course, and to some degree the Mac itself.

Notable virtues: Early in its existence, it was arguably a better way to turn a PC into a pseudo-Mac than Windows; it provided Atari computers with a decent interface into the 1990s.

What made it an underdog: All Digital Research products were underdogs to all vaguely comparable Microsoft products, for one thing. Also, Apple sued Digital Research over the PC version of GEM’s more-than-passing resemblance to the Mac, forcing a new version of GEM that was less Maclike and probably less appealing.

Random factoid: Like all defunct operating systems and environments, GEM isn’t completely defunct. It eventually ended up as an open-source application dubbed FreeGEM, available in distributions such as OpenGEM. Windows 7 it’s not, but it’s still capable of running on ridiculously underpowered old computers. As far as I can tell, though, things have been pretty quiet in GEMland over the last few years.

16. Microsoft Zune

What it is: Microsoft’s line of portable media players, starting with a hard-disk MP3 player in 2006 and currently focused on the new Zune HD.

Underdog to: The audio players made by a Cupertino, California company named after a piece of fruit.

Notable virtues: The new Zune HD has plenty of them–a slick user interface, a solid subscription-music service, HD radio support, and more. It’s not a pocket computer or an app platform, but on its own terms, it’s neat.

What makes it an underdog: The fact that Zune was from Microsoft made comparisons to the iPod inevitable, and inevitably made the Zune look bad; Zune sales (at least until the HD came out) have been pretty pitiful; a bizarre and embarrassing bug prevented all the 30GB Zunes from working on December 31st of last year. Zunes have always seemed like responses to iPod trends that Apple has already largely moved on from–hard-disk players, then simple flash-based ones, then touch-screen ones that don’t run third-party apps. Also, I think the name doesn’t help–it reminds me of the easy-to-make-fun-of malt beverage Zima and sounds nerdy rather than cool–the gadget equivalent of being a kid named Poindexter.

Random factoid: The first Zune had the pre-release code name of Argo, which might not have been a bad final moniker.

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