How To Checkmate Yourself

The parlor games hosted by Yahoo! once represented some of the internet’s best efforts at interactivity. But that didn’t last. Here’s how Yahoo! Games lost.

By Ernie Smith

Today in Tedium: This week, the world (for a brief moment) lost its collective mind after learning that Microsoft was planning to retire its legendary Paint software, which has a lineage that dates all the way back to Windows 1.0 in 1985. People calmed down some after learning that the company was creating an upgraded version of the app called Paint 3D, but make no mistake: As I hinted recently, big tech companies kill things people like all the time. Yahoo!, for example, last year killed something with a long legacy within the company, all in the name of “streamlining.” It was reliably square, but awesome. Tonight’s Tedium talks about the lost legacy of Yahoo! Games, and the technology that drove it. — Ernie @ Tedium

Lull Mattress

Advanced Sleep Tech: What makes a Lull mattress perfect for a good night’s sleep? Easy. A whole lot of innovation and some premium memory foam.

Lull is giving us a push today. Learn how to do the same.

Java Mascot

Duke, the mascot for Java. Oracle acquired Sun Microsystems in 2010. (Oracle PR/Flickr)

The technology that made it possible to build something like Yahoo! Games

In recent years, the word “Java” has become something of an annoyance for web users because of its constant security issues. But going back to around 1995 or so, it was genuinely exciting technology that blew a lot of minds.

Starting in 1991, Sun Microsystems began experimenting with a new kind of programming language designed specifically for interactive televisions, though when interactive TVs inevitably failed to generate heat, Sun and the language’s primary developer, James Gosling, moved the idea to the broader Web, which was just starting to grow.


A screenshot from HotJava. The graphics team at Sun was apparently a HotMess.

Sun’s goal with Java was to create a language that was able to run on a variety of platforms, not just Windows PCs, and in that spirit, Java’s developers experimented with putting Java code directly into the browser. The company created its own browser called HotJava, which was very limited except for the fact that it allowed for interactive “applets,” pieces of Java that could run in any web browser that supported them. It was a cross-platform compiler at a time when most stuff was siloed off. Java started a trend, one that other tools like Adobe’s Flash would soon follow.

One key element of that trend: Sun made it free, in hopes that it could change the dynamic of the internet and break apart Microsoft’s monopoly.

“Anything that contributes to the health of the Internet contributes to Sun’s health as well,” Gosling told The New York Times in 1995.

It was exciting technology, of course, but it was often confusing for users to keep up with it. As ComputerWorld’s Frank Hayes noted in 1996, Sun Microsystems was trying to sell the web on Java applets at the same time it tried to sell a different form of software to businesses as a way to offer cross-platform applications. That meant it was a lot for non-technical people to wrap their heads around. It didn’t help, either, that other companies tried to borrow Sun’s nomenclature, most famously with Netscape’s creation of JavaScript six months after the initial release of Java applets, something Netscape also supported.

One information consultant, Eli Lily’s John Swartzendruber, noted this created confusing situations at the office.

“People say, ‘We’re going to do this in Java,’” Swartzendruber told Hayes. “But sometimes they mean JavaScript, sometimes Java, sometimes applets. Oftentimes I don’t think they know what they mean.”

Java applets were novel and interesting—at least until they inevitably became bogged down by security issues, which doomed applets once and for all a few years ago. By that point, Flash, then JavaScript, had completely replaced it.

But back in the ’90s it took a couple of years for a killer app to emerge. And that killer app was one that brought board games and card games back to life.

“Checkmate / Dennis Bell of Torquay / Too late / With your N at e3 / Good game sir / Do you want another bout? / Well Dennis ain’t replying / Cause he just signed out”

— A few lyrics from Half Man Half Biscuit’s “Bad Losers On Yahoo! Chess,” which is officially the best song written about Yahoo! Chess. It is one of the more popular songs drummed up by the satirical masterminds, who have written similar tunes for more than three decades. In a love letter of sorts to the song, Irish Times columnist Donald Clark had this to say: “What makes it so funny? I think, more than anything else, it’s the hint that the Great Nigel Blackwell is not entirely joking. He has certainly pushed the pieces about on Yahoo and I fear Dennis Bell might be a real opponent.”

Deck of cards


How Yahoo! Games went from a small-time offering into a web conglomerate’s addiction play

Joel Comm is the kind of internet marketer that other internet marketers strive to be like.

His personal SEO is to die for. He writes books about internet marketing for a living. He’s been at this game longer than you’ve been using the internet, and it shows. (To give you an idea of how good he is at this: In 2008, his company built the most prominent fart app. Really.)

And perhaps, of the many big wins he’s had over the years, the biggest was what he did with a site called

Around 1995, Comm ran a site called WorldVillage, an internet portal which attempted a “virtual city” kind of experience, along the lines of Apple’s eWorld. (It’s still online today.) Around this time, he caught wind of a University of Southern California student was building—an online platform for parlor games, like checkers, chess, and poker. Comm reached out, cut a deal, and helped to market the site.

Comm’s family-friendly WorldVillage was something of a mainstream play, and he thought was getting involved in something niche with ClassicGames, a site originally called Springer-Span. But it turns out that people love playing games online. In a passage from his book Click Here to Order: Stories of the World’s Most Successful Internet Marketing Entrepreneurs he highlighted how he discovered this fact:

It was the Internet’s largest selection of Java-driven multiplayer games. In the beginning, given the total number of users online, I considered that a fairly narrow focus. But the Internet grew, and the site grew so fast we had to keep subdividing the users (three separate game areas became four, which became six) to keep from frying the servers—between November 17 and December 5 of 1997, the number of registered users jumped from 50,000 to 60,000. Finally it got so big that—oh, darn!—it caught the attention of a bigger company, who bought us out. The site is now Yahoo! Games.”

It helped that, beyond being fun, was a very effective model for interacting with other people online, with its chat-based interface and turn-based play. It asked less of its players, which meant it was perfect for casual gameplay.

“The funny thing is that these low-tech games work a lot better than the fast-trigger games when played on the Net,” writer Mark Glaser wrote of the multiplayer board game concept in the Los Angeles Times in 1997. “You don’t have to worry about your connection speed, buying an expensive CD-ROM game or being embarrassed by an overzealous competitor. Instead, you can play games often for free, sometimes without downloads, and you might meet someone interesting or win a prize to boot.”

(He did note that the Java applets were slow to load, however.)

The growth of, which only gained that name in July of 1997, was hard to ignore, even without a centralized portal to help it scale.

Yahoo Chess

And there was an obvious portal on a purchasing tear at the time: Yahoo!, which bought the site in 1998.

Around the same time Yahoo! bought, it purchased a company called Four11, which made an email service called RocketMail. That became Yahoo! Mail. And not too long after that, it bought Geocities and, two major acquisitions that eventually died on the vine. eventually would, too. But early on, it played an important role for Yahoo!, which was attempting to build, effectively, a web-native version of AOL—with content and activities so sticky that people would stay inside of its walled garden. Say what you will about checkers and chess, but they’re sticky games.

Unfortunately for Yahoo!, Facebook was simply better at building walled gardens.


The amount Yahoo! sold the domain for in 2010, according to Fusible. Yahoo! retired the domain by 2006 and had been trying to sell it for a few years by that point. Currently, the domain is a placeholder spam site. A pretty depressing state of affairs.

Yahoo! Games Spades

Yahoo Spades. The bearded male icon is based on Joel Comm’s appearance at the time. (via Joel Comm’s website)

How Yahoo! let a well-remembered platform die out in the face of corporate hubris

The concept that drove Yahoo! Games along with its predecessor—the idea that old-school parlor games are fun over the internet—was one that should have stood the test of time.

For one thing, it likely was a direct influence on the online poker boom of the early 2000s, as it was one of the first platforms to offer it. PlanetPoker, which claims to have been the first to offer real-money bids, did not start until 1998, while was active in 1997 with a poker server. (No betting, though.)

But Yahoo!, with its desire to be everything to everyone like an Everclear song, eventually diversified the site to an insane degree, moving far from the site’s roots as a simple arcade platform.

Here’s what it looked like in 2005, and here’s what it looked like in 2010.

To give you an idea of how far they moved away from the original idea: In 2010, the band REO Speedwagon launched a casual game on Yahoo! Games and other online portals, in an attempt to promote its music to casual gamers.

“There is a need for us to explore all kinds of different avenues to get our music out there,” lead singer Kevin Cronin told The New York Times. “If you just think about how it used to be, you’ll be left in the dust.”

The problem with Yahoo! Games is the same problem REO Speedwagon had: All people really wanted were the hits, but they kept delivering more product anyway.

And when mobile hit, Yahoo! couldn’t keep up, so they killed the site—first the classic games in 2014, then the platform altogether in 2016.

Joel Comm was not happy about the loss, writing in a blog post:

I was saddened to discover that Yahoo! recently retired the entire ClassicGames library from their site, leaving fans of the games completely in the lurch. In fact, there are many who are very upset about this, not understanding why Yahoo! would just pull the games completely.”

I can’t say I understand it either. But I know that the once mighty Yahoo! that had a chance to rule the web is alienating more of their user base with this move.

Was Yahoo! within their right? Sure. Was it fair to users? No.

Those servers weren’t hurting anyone.

Unlike the websites or platforms I usually mention here, Yahoo! Games cannot be recreated. The Internet Archive does not save experiences—no matter how important or fundamental those experiences are for internet culture.

And while the Java applet and Flash plug-in made the web more interactive, but it also made it easier to kill. At some point, we’re going to have to demand some corporate responsibility on the part of our tech giants.

Yahoo!, now owned by Verizon, should donate its parlor games platform—the old one, the one everyone remembers fondly—to someone willing to care for it.

Ernie Smith

Your time was just wasted by Ernie Smith

Ernie Smith is the editor of Tedium, and an active internet snarker. Between his many internet side projects, he finds time to hang out with his wife Cat, who's funnier than he is.

Find me on: Website Twitter