Numbers 6 to 10
6. Disney The Lion King CD-ROM (1994)
Few products get accused of killing Christmas for thousands of kids, but that fate befell Disney's first CD-ROM for Windows. The problem: The game relied on Microsoft's new WinG graphics engine, and video card drivers had to be hand-tuned to work with it, says Alex St. John. He's currently CEO of game publisher WildTangent, but in the early 1990s he was Microsoft's first "game evangelist."
In late 1994, Compaq released a Presario whose video drivers hadn't been tested with WinG. When parents loaded the Lion King disc into their new Presarios on Christmas morning, many children got their first glimpse of the Blue Screen of Death. But this sad story has a happy ending. The WinG debacle led Microsoft to develop a more stable and powerful graphics engine called DirectX. And the team behind DirectX went on to build the Xbox--restoring holiday joy for a new generation of kids.
7. Microsoft Bob (1995)
No list of the worst of the worst would be complete without Windows' idiot cousin, Bob. Designed as a "social" interface for Windows 3.1, Bob featured a living room filled with clickable objects, and a series of cartoon "helpers" like Chaos the Cat and Scuzz the Rat that walked you through a small suite of applications. Fortunately, Bob was soon buried in the avalanche of hype surrounding Windows 95, though some of the cartoons lived on to annoy users of Microsoft Office and Windows XP (Clippy the animated paper clip, anyone?).
Mostly, Bob raised more questions than it answered. Like, had anyone at Microsoft actually used Bob? Did they think anyone else would? And did they deliberately make Bob's smiley face logo look like Bill Gates, or was that just an accident?
8. Microsoft Internet Explorer 6 (2001)
Full of features, easy to use, and a virtual engraved invitation to hackers and other digital delinquents, Internet Explorer 6.x might be the least secure software on the planet. How insecure? In June 2004, the U.S. Computer Emergency Readiness Team (CERT) took the unusual step of urging PC users to use a browser--any browser--other than IE. Their reason: IE users who visited the wrong Web site could end up infected with the Scob or Download.Ject keylogger, which could be used to steal their passwords and other personal information. Microsoft patched that hole, and the next one, and the one after that, and so on, ad infinitum.
To be fair, its ubiquity paints a big red target on it--less popular apps don't draw nearly as much fire from hackers and the like. But here's hoping that Internet Explorer 7 springs fewer leaks than its predecessor.
9. Pressplay and MusicNet 2002
Digital music is such a great idea that even record companies finally, begrudgingly accepted it after years of implacable opposition. In 2002, two online services backed by music industry giants proposed giving consumers a legitimate alternative to illegal file sharing. But the services' stunningly brain-dead features showed that the record companies still didn't get it.
PressPlay charged $15 per month for the right to listen to 500 low-quality audio streams, download 50 audio tracks, and burn 10 tracks to CD. It didn't sound like an awful deal, until you found out that not every song could be downloaded, and that you couldn't burn more than two tracks from the same artist. MusicNet cost $10 per month for 100 streamed songs and 100 downloads, but each downloaded audio file expired after only 30 days, and every time you renewed the song it counted against your allotment.
Neither service's paltry music selections could compete against the virtual feast available through illicit means. Several billion illegal downloads later, an outside company--Apple, with its iTunes Music Service--showed the record companies the right way to market digital music.
10. Ashton-Tate dBASE IV (1988)
In the early days of the PC, dBASE was synonymous with database. By the late 1980s, Ashton-Tate's flagship product owned nearly 70 percent of the PC database market. But dBASE IV changed all that. Impossibly slow and filled with more bugs than a rain forest, the $795 program was an unmitigated disaster.
Within a year of its release, Ashton-Tate's market share had plummeted to the low 40s. A patched-up version, dBASE IV 1.1, appeared two years later, but by then it was too late. In July 1991 the company merged with Borland, which eventually discontinued dBASE in favor of its own database products and sold the rights in 1999 to a new company, dataBased Intelligence, Inc.