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SoftwareMedia Blog | May 24, 2016

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Top 19 Worst Software Programs of All Time

Top 19 Worst Software Programs of All Time
  • On November 8, 2010

There is some truly amazing software out there. Revolutionary products that have changed the way we live, interact and do business. However, there are also some real stinkers. Programs which are long past due, riddled with security issues and malware, software that holds innovation back, and, in short, are just plain bad.

Here is a subjective list of the twenty worst. Settle down Microsoft-haters, Bill Gates’ creations only appear 5 times on this list. Even the usually squeaky-clean Apple gets a few drubbings too.

So come along as we take a not-so-pleasant ride down memory lane to look at some of the most annoying software the IT world has turned out to date.


19. MS-DOS

Yes MS-DOS was a breakthrough operating system, and sure DOS holds a nostalgic view for many PC users. They remember the good old days of text-based games, Word Perfect, and fun commands like “cd\” and “dir *.*”. However, do you remember this one: Bad command or file name, bad command or file name. DOS made computing accessible to only select few and provided endless hours of frustration for the rest. DOS was a pain, and I for one am glad it is long gone and buried.


18. Apple iWeb

Lately it seems Apple can put a lower case i in front of anything and have a best seller on their hands. But not all Mac programs were amazing or revolutionary in their times. Bundled as part of their iLife project, Apple’s iWeb was an attempt to bring webpage creation to the masses. It failed miserably. iWeb was just a bit too simplistic; it didn’t create real web sites. For example, try highlighting some text on an iWeb created site. You can’t! That’s because iWeb didn’t add text or hyperlinks to sites, it simply created an image which you could upload to server, a sort of pseudo-site if you will.

17. Compuserve

Think way back to a time when the internet was brand new and the possibilities seemed limitless. Compuserve was an attempt to one-up AOL. It was an early version of Second Life in a way. Users would create a cartoon avatar that would then be able to explore an online Compuserve world with various houses to enter that represented areas of the web: news, sports, chat rooms, ect. The problem was it didn’t really work, was plagued by horrible connection issues, and once the novelty wore off, people soon realized surfing actual websites was far superior.

16. Realplayer

I will admit thatRealplayer does have it good points. Its Flash support for iPhones and Blackberries is great and it has been successfully integrated into Xbox, PS3 and Wii. However, as a stand-alone version Realplayer is basically a virus; it works its way into every nook and cranny of your computer. It always pops up asking you to install updates or download the latest version. And it’s clunky and slow. All-in-all, Realplayer is just a pain in the butt.

15. Pay-Service Napster

When Napster was first released it revolutionized the internet and the music industry. Free music, whenever, wherever. And you could just download single songs, no longer were you forced to shell out $20 for an album full of junk to hear that one hit single. Then reality smacked Napster users in the face. It turned out all those free music downloads were actually illegal and Napster had to become a pay service. Well, since then the program has basically become useless as others like iTunes have taken over. Napster is a prime example of a good program gone bad.

14. Comet Cursor

At number 15 is an evil little menace you might remember from the late-1990s. In the pre-2000 age of computing, words like spyware, adware, and malware, had not been added to the collective lexicon yet. We have the industrious Comet Cursor to thank for that. This little program, designed to help those who just could not live with the standard white arrow cursor, single-handedly initiated the malware plague that currently infects cyberspace. Many a beginning, younger, or less-knowledgeable internet surfer fell prey to this lurking predator. Before they knew it, their system was completely bogged down spyware and adware. If you remember your old computers for being slow….perhaps they just had Comet Cursor installed on them.

13. Microsoft Bob

Microsoft was always acutely aware that their software and operating systems could be intimidating for first time users. In order to solve this problem the software giant developed what was supposed to be a non-technical interface for beginning users. Know as Bob, he (it?) was integrated with several key applications for easy use, such as a word processer and financial software. Users would navigate these sections of Bob, graphically displayed as “houses” (sound familiar?). Bob also had several other cartoon helpers that dwelled in this digital neighborhood. The problem with Bob was it was just too silly. Adult users quickly grew tired of the hand-holding and by Windows 98, and Bob was abandoned.

12. Bearshare

In the days after the demise of good old free-to-use Napster many new contenders to the throne of “free download” king emerged. Bearshare was a highly popular one. For a while, at least before it too was brought down by a lawsuit, Bearshare allowed users access to a Napster-esque amount of free music downloads. Unfortunately, Bearshare also gave you access to a host of spyware, adware, viruses, malware, and encrypted packets which Napster did not. It was one of the original wolf-in-sheep’s-clothing freeware programs that so pollute cyberspace these days. Top it off with disorganized search results and an overly segmented and congested network, and you have one terrible Peer-2-Peer program.

11. Apple Time Machine

Not all Apple products are a flawless blend of technology and innovation, and Apple’s system backup program Time Machine is a perfect example. Again, the problem seems to be one common to most flawed Apple products: it is too simplistic. Apple TM allows users to restore their files to the exact condition before a HD crash occurred. Sounds fair, the only problem is that is about all it does well. There is simply no customization. Users cannot select which files to backup, only which to exclude. They can’t pick when the backup times occurs, TM just automatically backs up files on a drive at certain intervals. Not all Mac users are computer-illiterate, but sometimes it seems Apple likes to pretend they are.

10. Nero Burning ROM

Not so affectionately nicknamed “Nero Burning Rome” by frustrated users, Nero was once the king of optical disc authoring software. Now Nero more resembles the tyrannical Roman Emperor whose namesake the software bares: overly extravagant and controlling. At a price tag of between $100 and $200 dollars, Nero is highly over-priced considering the wealth of free ROM-authoring software available. Additionally, Nero has Microsoft level control issues. The hundreds of dollars spent buys you 1 license, so if you have two computers you will have to buy two copies of Nero…sound familiar? Don’t even bother with this dinosaur.

9. WinFixer

Also known as Driver Cleaner, WinFixer claims it “is a useful utility to scan and fix any system, registry and hard drive errors. It ensures system stability and performance, frees wasted hard-drive space and recovers damaged Word, Excel, music and video files”. What WinFixer actually does is implant your system with more malware, spyware and adware than you can ever hope to get rid of it. WinFixer has been the subject of numerous class-action lawsuits by duped clients who said the program irrevocably damaged their hardware. The people who created this monster should be ashamed of themselves.

8. Windows Vista

After 6 years in development, Microsoft trumpeted Vista as a Win95-like revolution in operating systems. Soon even Microsoft itself has to admit Vista was fatally-flawed, and as an olive-branch, they extended service for XP longer than originally planned. Vista had massive hardware requirements and was ridiculously expensive – $399 at release! However, what stands out in user’s memories is that almost comical amount of user prompts associated with the product. “Program X wants to access your system: Cancel or Allow”. This phrase quickly went viral and was even spoofed by Apple during their famous Mac guy versus PC guy add campaign. Vista also has a host of technical problems that are beyond the scope of this review. Needless to say, Vista caused many a new PC purchaser to break out and reinstall their old copy of XP or Windows 2000. Luckily Windows 7 has been a complete turnaround for the Redmond-based company.

7. Apple Quicktime for the PC

Quicktime remains an essential program on the Mac; however, their PC port is one of the worst video playback platforms available. The PC version of Quicktime was slow, had terrible buffering rates, embedded itself deep in your system, and for the most part exhibited low-quality playback. While Windows Media Player would give you full- screen clarity at decent speeds, Quicktime would open these tiny little windows in your internet browser that took forever to load. How PC Quicktime ever became so popular is beyond me.

6. Internet Explorer 6

To be honest, I’d like to just put the whole Internet Explore family on here. However, for the purposes of clarity I will limit it to the black sheep of an already questionable family. IE 6 was so riddled with security issues at many points it seemed like Microsoft must have been in league with the spammers and scambots. With virtually no protection against unwanted cookies, adware or spyware, IE 6 opened the floodgates for the rise in malware over the recent years. Lack of standards for web development… I could go on about the problems still abound with IE6. In January 2010, Google announced it would discontinue support for IE6. Often derided as one of the worst programs ever, IE 6 comes in at number 7 on this list because of its one saving grace….it precipitated the ascendancy of Mozilla Firefox.

5. Lotus Symphony and Jazz

Released as the successor to the highly successful Lotus 1-2-3, Symphony was an integrated office suite released for both PC and Apple (called Jazz on Apple) in 1985. Perhaps they were trying to capitalize of the name recognition generated by Lotus 1-2-3, but Symphony and Jazz held a whopping $600 dollar price tag. (This is 1985 mind you!) Additionally, the UI was crummy and ugly, and the program was very basic and slow. The demise of Lotus allowed Microsoft to swoop in and corner the market with their Office suite, a domination that still exists to this day.

4. Microsoft Works

Next up is another integrated office suite, the poor man’s version of Microsoft Office, collectively known as Works. Microsoft Works is an enigma of sorts, a dog without a home. It has no point really; it is obviously far inferior to Office. Its output, .wps files, are not compatible with Office, nor can you open Office files easily in Works. It seems to be a frustration purely created to entice users to buck up and spend the $100 dollars on Office. Heck, even the logo is crummy!

3. MyWay Searchbar

This was a search tool that would automatically query search engines like Google, Yahoo, Alta Vista, and then combine the results into one list. Sounds like an OK idea. However, like many other programs on this list it was riddled with malware. MyWay would overload your computer with popup ads and install all sorts of nasty and annoying cookies into your system and browser. This program was also designed to integrate with such wonderful internet options like SmileyCentral, Cursor Mania, Popular Screensavers and Zwinky…oh joy. The worst part of all was that Dell Computers used to ship this program already installed on Internet Explorer 6!! Could anything be worse? Actually, 3 things could….read on to find out.

2. Windows ME

Forget Vista, worry not Works, even poor old IE 6 can’t hold a candle to the sheer garbage that was Windows ME. Universally regarded as the worst operating system of all time, ME, or Millennium Edition, is evidently where the actual Y2K bugs ended up. ME was shockingly unstable, it would crash for no reason, freeze when it felt like it. It was like some evil little elf out to frustrate users into switching to Apple. A PC World report stated that “users reported problems installing it, getting it to run, getting it to work with other hardware or software, and getting it to stop running.” ME, dubbed Mistake Edition, would actually resurrect cleaned spyware and adware during the system restore option!

1. America Online (AOL)

The largest “walled-garden” online community is the number 1 worst software program of all time for a litany of reasons. Alone, any one of these would be enough to put AOL in the top 10, together, they push it to the top. Firstly, how may AOL discs did we get in our collective mail, hundreds, thousands, millions? Somewhere there must be a landfill the size of Delaware full of free AOL CD-ROMs and 3.5” inch floppies. But I guess these were the days before we knew to be environmentally conscious….. right?

Second, AOL fed users into this weirdly controlled online pre-school where bad content was kept out and only websites with “AOL keywords” could be accessed, while at the same time the “teen” chat rooms precipitated the mass-wave of internet predators and pedophiles. AOL didn’t have email…it had “goodmail” where by users wouldn’t get spam, they would only get emails from “trusted” companies. OK so no spam, just emails from whoever paid AOL enough money to become “trusted”.

Anyone remember the AOL search data scandal of 2006? That was when AOL made public the search history of 650,000 AOL users. Ever try to cancel your account? It was a challenge, that’s because AOL had an elaborate employee reward scheme set up to give bonuses to employees who could retain users attempting to cancel their accounts.

Most damningly, and the main reason AOL is number 1 is their efforts to delay the mainstream acceptable of broadband. DSL and cable-based internet access would cut into AOL’s bottom line, they preferred you to remain on 56k and pay $19.95/month for it. Although AOL now offers DSL access to its clients, their foot-dragging on broadband remains a dark-chapter in internet history. For all of these reasons, AOL is the worst software program of all time.

And there you have it folks! The top 20. Or shall we say, bottom 20? Know of a horrible program that didn’t make the cut? Add it to the comments below and we will consider it for a followup post.


SND would like to thank our guest writer Alex for this interesting take on software history.


  1. Dan

    Where is Flash Player? It is the spawn of Satan.

  2. I am having trouble with Stellar Data Recovery for QuickBooks. The software doesn’t work for its stated purpose, tech support is not helpful and sales support requires you to fill out forms to attest to the fact that the software that does not work has been destroyed – as if someone would want to use software that doesn’t work.

  3. John Smit

    Come on, MS Works was rubbish but I would pay money to use it rather then that train wreak called iTunes for the PC, the worst PC program ever!!

  4. You’re an idiot. The only reason iWeb makes your text into graphics (so you can’t highlight some) is because you used a non-web font. If you use web-friendly fonts you can highlight and copy text from an iWeb site just fine.

    iWeb is the finest website creation tool ever invented for Mac. I don’t care that Apple doesn’t get this. iWeb is a Rembrandt. Feel like painting “improvements” over a Rembrandt? There it is! You’re an idiot.

    I would rather stop the OS parade than lose iWeb. Truly, you have a lot to learn.

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