Like the internet phenoms they trumpeted, Internet company names of the last decade have been, by turns, wildly inventive, deeply troubled, breathtakingly silly, serviceable (if dull)—and, occasionally, brilliant.

Having christened our share of Internet phenoms, we at Catchword decided to looked back to identify the 10 biggest dot-com naming trends—and their best and worst examples.

(Although, frankly, it was hard to choose just one “worst” in some cases. There were so many Web 2.0 disasters! It was as though the rules of language had ceased to apply.)

Here are the trends and names that rose to the top (and sank to the bottom).

1. The Hookup

But if two words don’t have a discernible relationship with each other—or the brand—it’s a Random Hookup. And we all know how short-lived those are—in this or any realm.

Win: YouTube

Intuitive, catchy, grassroots-y. The retro slang “tube” for TV evokes simpler times and ease of use: clever for a new app that could have been seen as intimidatingly high-tech.

Fail: TalkShoe

Say what? The name is a play on the use of Ed Sullivan’s pronunciation of the word “show” on his long-ago TV show. Like anyone is going to make the connection…

2. The Conjurer

Evocative words can make memorable brand names when they relate to the core of a brand’s story (like Yelp). But the line can be fine between edgy and baffling.

Win: Twitter

Whimsically conjures up users’ sharing short little bursts of information (like birds twittering in a tree)—as well as excitement (”all atwitter”). It’s extendable, too. A whole vocabulary quickly takes flight—from tweet and twitfriend to twipic.

Fail: MOO

Great for cows, milk, cheese, ice cream. Not so great for a site offering printing services.

3. The Letter-Dropper

The problem with this type of coinage is it’s so distinctive you’re almost bound to look like a copycat if you’re not the first out of the gate. And if you drop more than one letter, you’re asking for trouble. (Was Motorola’s SLVR cell phone meant to be Silver or Sliver? And what’s with Scribd?)

Win: Flickr

The image of a camera’s flicker is relevant for photo sharing and reassuringly familiar, while the dropped letter—a new naming convention—suggested cutting-edge technology.

Fail: iStalkr

Creepy.

4. The Assembly Line

Names assembled from word parts with meaningful associations can be rich and unexpected (witness Gizmodo, the gadget blog). But tone and messaging need to be just right.

Win: Wikipedia

The unusualness of the name establishes it as a fresh player, while the evocation of both encyclopedias and speed (”wiki” is Hawaiian for “quick”) is spot on.

Fail: Nupedia

The flatfooted claim of newness sounds dated from day one. Plus it’s risky to stake an identity on newness in internet-land. Before long, this premise is far from “nu.”

5. The Misspeller

This kind of brand name often spells disaster: hard to remember (Ideeli, Scrybe), confusing to pronounce and spell (Myngle, Wotnext, Gravee), and reeking of URL-search desperation (Itzbig, Profilactic, Fairtilizer).

Win: Boku

French word “beaucoup” is on the money for an online payment service—and for many Americans, the misspelling is actually more intuitive and inviting.

Fail: Cuil

Meant to be pronounced “cool,” but who’s gonna get that? Rule No. 1: Your name shouldn’t need to come with a pronunciation guide.

6. The Wordster

Another convention that ages fast. And there’s nothing more pathetic in naming than a transparent attempt to appear cool (cases in point: Dogster, Agester, Talkster).

Win: Friendster

Not exciting, we’ll grant you, but the intuitiveness of the name helped usher in the era of social networking.

Fail: Napster

In light of its ensuing legal woes, to highlight the “kidnapping” of music is probably not the best idea (to put it kindly).

7. The Double or Nothing

Doubling a letter in a real word only works when the word remains recognizable, and the addition of the second letter serves some purpose, other than to complicate spelling (as in Gawwk).

Win: Digg

Intuitive and evocative, the double “g” underscores the digging nature of research and is graphically interesting.

Fail: Diigo

A social bookmarking site, the double “i” destroys the semantic connection and confuses pronunciation. (Is it Dee-go or Dih-go?) Plus, coming on the heels of Digg, it seems hopelessly derivative.

8. The eThing, the iThing, the meThing, the myThing

“e/i” shorthand quickly becomes redundant in the internet space, although it spawns many workhorse names: serviceable, if dull. The me/my thing (as in mySpace) tends to be similarly predictable and unremarkable. (Now, myBad—that would be interesting…)

Win: iContact

For a provider of email marketing, the “i” works on three levels: “I contact,” “eye contact,” and, of course, “Internet contact.”

Fail: eSnailer, eBaum’s World, eXpresso…

9. The Empty Vessel

A word without recognizable semantic roots can be a useful umbrella name for a company that may want to branch out in different directions. But it needs to be pronounceable and have relevant sound symbolism. Otherwise, it’s not an Empty Vessel—it’s Alphabet Soup. Like Disaboom, Xoopit, Yebol, and Goozex. Cover your ears.

Win: Kazaa

Recalls huzzah or hurrah, conveying excitement. (Sample exclamation: “Kazaa! I just downloaded Season One of Six Feet Under, FOR FREE!!!”)

Fail: Eefoof

Vintage Web 2.0: hard to spell, silly—and utterly meaningless.

10. The Foreigner

Words in little-known languages can also make good empty-vessel names, especially if their meaning provides a springboard into their brand story. The trick is to find words that are easy to pronounce and pleasing to the American ear (like Kijiji, a communal website with a Swahili name meaning “village”).

Win: Hulu

Good empty vessel name for an entertainment company that wants to keep its options open. (Interestingly, the word means “empty gourd” in Mandarin.) The rhyming word is playful, and by evoking hula hoops, it suggests fun.

Fail: Jwaala

Talk about a tongue-twister.

The Coming Decade

As for Internet company naming trends of the coming decade: Companies will demand more meaningful brand names, as far from Web 2.0 flights of fancy as possible; they’ll be willing to pay a premium for real-word or lightly coined domain names; and they will be creative in the messages they explore—as long as they’re relevant to the brand.

Like Internet companies themselves, it appears, Internet naming will be coming back down to earth.

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