Top 5 Best and Worst Microsoft Products
March 29 Carl Nelson
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According to our web stats, if you are a reader of this site, there is a 96% chance you’re using a Microsoft OS. So you know as well as I do that love ‘em or hate ‘em, Microsoft is still the best choice for most people to have on their desktop PC’s right now.
Microsoft does more than just operating systems of course, and this is where they have to work even harder to win customers over. Some Microsoft products have been famously bad, while others have been very good. Some of Microsoft’s initiatives are simply taken for granted, which is why I decided to do a writeup on what I think are some of the best and worst product in the infamous company’s history.
#5 Best: Microsoft Streets & Trips
This is one that most people take for granted, now that we have Google Maps to do quick address searches online. But before Google Maps, our online choices were AOL’s MapQuest and Yahoo! Maps. A few years ago, those sites offered decent functionality and served well for basically looking up addresses and sometimes get directions. But Microsoft’s Streets & Trips was much more robust, giving multiple destination routes, multiple route choices (set based on speed or distance - sometimes the most direct route isn’t the quickest). The routes were also highly customizable; simply drag the route line to wherever you like, and it will make the adjustments for you. You could set your car’s fuel economy stats, and the program will tell you when you should stop for gas on long trips.
On top of all that, it was compatible with Pocket PC devices, so you could take it with you on the road, back when portable internet connection was somewhat rare.
Many of these features are still unavailable on the internet based maps programs, so Streets & Trips is still worth looking at. It was probably one of the MS products I used most besides Windows.
#5 Worst: Internet Explorer 6
IE6 almost lead to the downfall of Microsoft, but that’s not why it’s one of their worst products ever. IE6 is quite possibly the least secure product that is so widely used; almost every week there are new security holes being fixed. Because of this, Internet Explorer saw its overall market share drop from about 82% down to 49% in the past year alone. We should mention however, that the browser is a huge target for hackers to begin with. Microsoft has to accept some blame though, for making it so easy for hackers to pick their browser apart so easily. IE6 is easily one of the top 5 worst Microsoft products ever, and that’s not even taking into account the issues with compatibility with web standards.
#4 Best: Verdana Font
You’re looking at it right now. Verdana was created in 1996, but really didn’t come into its own until people started using higher resolution. Verdana is a very easy to read font at smaller sizes, making it perfect for websites that are mostly content driven. I like this font so much, I have taken to using it in my emails, online chats, and printed documents. Despite how suitable Verdana is for smaller font sizes, it stands out even more at larger sizes. Verdana is a very robust font, and one of Microsoft’s most overlooked products.
#4 Worst: Live Search
Microsoft’s competitor to Google left beta in September of last year, but you wouldn’t know it if you ever tried to use it. Although the search results aren’t nearly as bad as they were during beta, there is just no compelling reason to switch to Live from Google.
One annoying thing I just came across now (as I wanted to test out Live Search a bit while doing research for this article) is that a search result’s URL is not given as a direct link. Instead, you get a link that forwards from Live.com to the site itself… Just one of the many annoyances that make me wonder if Live Search really is out of beta.
#3 Best: Windows TweakUI
This was a small download hidden within the depths of Microsoft’s website, and sometimes showed up on Windows install discs. It is basically a small user interface application that allows you to tweak various Windows settings without having to dig through the registry. Whenever I install a copy of Windows (and going back to Windows 95, this was a LOT), the first task is always to go through TweakUI and change the settings to how Windows SHOULD be.
Some of the best tweaks are setting the Start Menu to load instantly on mouse hover (called Menu Speed), as opposed to waiting 0.5 seconds (or clicking) to browse. I also always made sure to disable “detect accidental double-clicks” which is what causes that annoying delay when you click text forms in IE (back when it was the only really compatible choice). Other little tweaks are there to allow you to make Windows look the way you want it to; disable the “Shortcut to:” text that is added when you make a shortcut, or set an automatic login if you need to. At one time, all the AutoPlay settings (when you insert media) were only found within TweakUI as well, so some of the settings have found their way into Window’s normal Control Panel.
TweakUI is now a part of PowerToys for Windows XP. I don’t think they have a version for Vista yet, although Vista is highly tweakable to begin with. Still, I really would like to disable the Start Menu delay…
#3 Worst: MSN Smart Watch
A few years ago, they were giving these away at CES to anyone who would take them… Back then it seemed like more of a tech demo of SPOT technology than an actual product. But sure enough, several watch manufacturers signed up, and to this day you can actually buy a watch that will tell you the weather (as if looking out the window is that hard) or tell you the score of the hockey game while you’re at that tedious wedding dinner (in case you are somehow unable to sign up to an SMS service with your phone). The technology (which is based on FM, not WiFi or GPRS) is pretty cool, but the products are definitely not. If they opened the technology a bit, I think some creative people could do great things with it.
#2 Best: Windows Media Player 11
As much as I hated WMP9, I became a big fan of WMP10. But then I installed Vista and got to try out Windows Media Player 11. Wow.
The new graphics-based listing is absolutely perfect, and allows you to sort through even the largest music collections with ease. CD covers are ’stacked’ to represent a pile of CD’s sorted any way you wish; via artist, genre, or year of release. The wheel-based search makes it even better, as results are shown as you type in a search phrase.
Media Sharing is another nice feature, and allows videos, music, and pictures to be easily shared across a network to PCs and even the XBOX 360 without the need to jump through hoops to allow access to the other devices.
#2 Worst: Microsoft Bob
This is almost too easy… Even if you don’t recall ever using Bob, you would probably recognize the name and the stupid smiley face logo anywhere. I’m not sure whose idea it was, but possibly because the product manager was Bill Gates’ girlfriend, nobody wanted to say that it was a stupid idea to turn the Windows interface into a cartoon. That’s right, Bob was intended to be the new interface for Program Manager. Instead of boring old windows and icons, you would be able to explore cartoon Bob’s cartoon living room, with help from his dog, Rover. If you’re unfamiliar, it truly was as stupid as it sounds.
#1 Best: XBOX 360
Despite the venom I spat in the direction of the Elite Edition yesterday, the XBOX 360 is a pretty damn good gaming system. Ask any game developer, and they will tell you that the 360 is the better platform to develop on, so any multiplatform game will be native on the 360 and ported to the rest. Graphics will be better, and it has by far the best game library of the 3 newest consoles today.
I won’t turn this into another XBOX 360 vs. PS3 debate, but the fact remains that the XBOX 360 is a very good gaming system, a pretty decent multimedia system, and easily Microsoft’s best product to date.
#1 Worst: Windows Millennium Edition
Do I even need to explain? Easily the most maligned version of Windows since the first few versions, there was really no need for anyone to ever use Windows ME. It didn’t offer much over Windows 98SE, except the (admittedly pretty useful) System Restore function. Aside from that, WinME was packed with bugs, incompatibilities, and a general feeling of overall shittyness.
Honorable Mentions:
- Sidewinder Freestyle Pro - Before the Wii Remote and the Sony SixAxis, there was the Freestlye Pro, the first motion-sensing controller from a major manufacturer. Unfortunately, it wasn’t very precise at all, and most games were unplayable with it. Still, it gets points for being innovative
- MSN Messenger (now Live Messenger)- Sure it’s a bloated ad-infested piece of crap, but how many of you have switched from using ICQ to MSN Messenger? It took me a while, but eventually it became my exclusive IM program.
- Pocket PC Smartphone - There’s no question that the PDA market is dying, but thanks to the robust Windows Mobile OS for Smartphones, it’s at least on life support for a while. You wouldn’t believe how many times it has come in handy to have what is basically a PC that truly fits in your pocket. Add a camera and GPRS connection and you will be as much like Jack Bauer as possible without having to kill 3 men with your bare hands while handcuffed to a chair.
- Windows Media Center Edition - The idea is simple; create an interface for Windows to be used on screens being viewed from 10 feet away, while still offering all the functions one would need from that perspective. In other words, MCE is a great all-in-one solution for a basic Home Theatre PC. 3rd party options are sometimes better, but now that MCE is integrated into Vista, it deserves recognition as a good product from Microsoft.
Dishonorable Mentions:
- Office Assistant - Much like Bob, this was intended to make computers more accessible to n00bs. Unfortunately, it treated you more like a complete moron. Everything “Clippy” could possibly tell you could be easily found just by hitting F1 and doing a search. Instead, you will have to deal with a lame animation and cheesy dialog. Even turning it off was annoying, as you had to wait for the final animation to finish once you disabled it.
- Ms. Dewey - Although not really an official commercial product, Ms. Dewey was introduced as a viral marketing campaign to promote the Live search engine (our #4 worst Microsoft product ever). Despite the fact that the actress playing Ms. Dewey is absolutely gorgeous, the site is nothing more than an extreme example of Flashturbation remnant of the pre-dot-com bubble burst. To top it all off, the character’s reactions suck, rarely matching what you typed in.
- Tablet PC - I didn’t put this on the main list, because for some people these are EXTREMELY useful. But for the remaining 99% of us, they are prohibitively expensive and buggy. There is still a small but strong contingent of people who rely on these daily however, so they’re not going anywhere, especially as wireless internet access becomes more readily available throughout the world.
- Mira Smart Displays - Imagine being able to pick up your LCD monitor this very moment, and being able to walk to another room while still being able to control small portions of your Windows XP system. Imagine the possibilities! I mean you could… umm… well… never mind. Just consider it one of the many ’solutions with no problems’ from 2002.
Filed under: PC Hardware, PC Software

nice articles. should add #worst microsoft frontpage template engine.
The Office Assistant was based on the same technology as Bob. I’d argue it was worse, since at least Bob was an experiment to change the overall paradigm for human/computer interaction, while Clippy was an idiotic grafting of this failed paradigm onto a business application.
And Excel rocks. And Visual Studio is pretty good, too.
I personally think WMP11 is bloated and horribly inefficient for what it does. Songbird and Amarok are definitely faster to use for finding songs etc.. And songbird is still in beta.
I must be one of the only people who liked the office assistant, while learning office 97 i thought it was helpful enough suggesting things that i wouldn’t have thought to ask (oh and i changed my assistant to Rocky the dog :) ) - Pocket PC’s with windows mobile - LOVE THEM, sidewinder - hated it sooooo much, Windows ME worked fantastically for me - but i dual booted Win2k as i had a dual CPU machine at the time and i was a gamer so ME for the Games and 2k for productivity - Media Center Edition has changed the way i use my tv forever had it for over 2 years now and couldn’t live without it - i alos fell in love with MP10 the same way i loathed 9.
Actually I hated WMP 11 so much in the first few minutes I rushed to remove it from my system, praying that I could rid this crapplication from my system without damage. Listing everything with a CD cover just made everything so much more difficult to do. Really who cares about the cover of the CD when all you want to do is listen to the music? I think reading the title is so much more use than looking at the cover. I’d put this as one of the worst, not the best.
WMP 11 is trying to do too much with features that just aren’t necessary. 10 is still the better player IMO.
your URL for power toys is incorrect ;)
besides that very good read, I agree on all points
John.
A good read, and I tend to agree with most of your commentary although I can’t post any experiences with Vista or MP 11 as I have much bigger personal issues with Microsoft than the ones you have had. I stopped using Windows and supporting MS with XP as I just got fed up with verifying, activating and reactivating via some guy in India who, at times, I could not understand. This all forced me to call back and hope to get somebody I could understand. Now, couple all of that with the 42 digit procedure and I had reached my limits. I cannot understand nor agree to any software license, it’s terms or conditions which force me to prove to MS that I’m using a legal copy of their software. My point is, if I buy the rights to use their software, I shouldn’t have to prove it’s theirs. This is not right, nor should MS force people to do it on their time and at their expense.