Hmm, I think the list catalogs combinations of success/notoriety vs. poor technology/bad business practices. In other words "stuff that should never have been a success". Maybe the name of the list is just wrong.
I mean yes we can all agree there have been worse "tech products" - any genuine spyware qualifies admirably. But I think I get what they're aiming for here and given that I don't think the list is that bad. Sure it's a bit knee-jerk and based on "one side of the story", but I think there's a reason AOL and RealPlayer have the reputations that they do. They earned them. And the article goes into specific reasons why, which I think are pretty much all valid.
They do also give a bit of "credit where it's due": "To be fair, RealNetworks deserves credit for offering a free media player and for hanging in there against Microsoft's relentless onslaught. We appreciate the fact that there's an alternative to Windows Media Player; we just wish it were a better one." or "To its credit, Me introduced features later made popular by Windows XP, such as system restore. Unfortunately, it could also restore files you never wanted to see again, like viruses that you'd just deleted." Even though it's a bit of a booby prize.
They even acknowledge exactly what Jazper pointed out - IE's vulnerabilities are so well-known in part because of its popularity.
I do think the article is a bit heavy on the mindless MS bashing and that probably exposes the true mindset and perspective of the authors. But hyperbole notwithstanding their list is again not that far off IMO, given the right criteria at least. What I mean by that is for example AOL being above Bob - well, AOL had more success and a wider reach, so if it is to be considered a "worst tech product" it is worse by the fact that it succeeded more. That seems to be the general approach they're taking and I don't really disagree with it. Perhaps the list could have been named "The 25 tech products that were most succesful in spite of themselves" or something.
It does seem like they're scraping the barrel for good ones after the top 10 though - maybe some of those could have been replaced with more notables like Gator. Then again it seems like they're trying at the same time to back up their "25 years covering the PC industry" claim by putting some of the older stuff on there.
Btw re: RealPlayer and its "accomplishments" - remember that they're targetting RealPlayer, not the format and not the company.
Yes Real pioneered some good streaming video/audio tech. But the player was always awful and the fact that it was proprietary was part of its big problem. So even though the tech may have been great, it was tied to something that wasn't great, just like so many other company's products. Ultimately a mixed bag at best. Fortunately you don't need RealPlayer to play Real content these days.