Happy birthday, Windows 2000, and try not to get too hung over

On this date ten years ago, Windows 2000 launched in San Francisco.

One of my colleagues was working as a staff member at the Windows 2000 Conference and Expo in San Francisco, an event which accompanied the Windows 2000 launch event. Also working at the event was his boss's boss, and the two shared a hotel room.

Their flight back to Redmond wasn't until late in the afternoon, so they decided to spend their last day in San Francisco being tourists in their host city. Hopping on a cable car, walking down the crooked street, seeing the sights in Chinatown and Fisherman's Wharf, all the standard tourist stuff. My flight was also not until late in the afternoon, so I decided to join them.

The morning of our planned day as tourists, my colleague lay in his bed hung over from a night out drinking with local friends at a place called The Thirsty Bear.

We gently woke him up. "Hey, Bob, it's N o'clock." (Where N = the time they agreed to get up.)

grmgmergmrgmrgmmrgmrmgrmgm. Why don't you go down and have some breakfast.

We went downstairs and had a leisurely breakfast in the hotel restaurant.

"Hey, Bob, I'm back. Are you ready?"

frgfrgfrgfggfrgrfrgr. Okay, I'll be down in the lobby in 30 minutes.

He pulled himself out of bed and managed to make himself presentable enough for the day.

When my colleague returned home and told the story to his wife, she was absolutely horrified. "You went on a business trip with your boss's boss, and then you went out drinking with your friends, and then the next morning, you were too hung over to wake up on time and made your boss's boss wait in the hotel lobby for you!?!?"

Well, yeah.

What she didn't know was that Bob and his boss's boss were actually good friends, so this wasn't actually a career-limiting move.

Though I personally wouldn't recommend it.

Bonus chatter: When asked where to get off for Chinatown, the cable car operator said, "You want to get off at the next stop, and then walk in that direction until you can't understand the signs any more."

Comments (24)
  1. Ah, Windows 2000 I remember you well.  I think 2000 was probably my favorite Windows version.

  2. Marquess says:

    Win 2000. Lean and clean, but also somewhat limited. But I did hold onto it until Windows XP x64.

    <remark type="snarky">And it was also the last Windows without that silly activation thing.</remark>

  3. John says:

    Yeah, Windows 2000 was fantastic.  I still think I like XP just a tad bit more, but it’s very close.  The shell changes in Vista were a bit too dramatic for my tastes, but I suppose I’ll get used to it eventually.

  4. ERock says:

    I would still be using Windows 2000 if it didn’t have a weird habit of refusing to redetect a USB device inserted after it was ejected. So, if I had a 14 day up-time, that USB flash drive I inserted on day 2 and ejected I would reinsert on day 14 and have to go through "Add/Remove Hardware" to get it to initialize. Don’t know if it was a Windows thing of a USB driver thing, but upgrading to XP took care of it.

  5. Marcus says:

    Nah.  I used Windows Server 2003 as my desktop OS for many years and it was a much better desktop OS than Windows 2000 (well, except for the stiff price). It’s just as clean and trim as Windows 2000 but had everything that XP had when you wanted it.  

    Though it’s 2010 and I suppose it’s time to move on, I really haven’t much liked any MS OS since WS2003.

  6. Gabe says:

    One would hope that you wouldn’t share a hotel room with your boss’s boss unless you were pretty good friends with him already. It’s not like Microsoft is the kind of company where you would have to share a cheap hotel room with whomever you’re stuck with.

  7. tsrlbke says:


    They could also be thrifty, I know of some places that return a percentage of unspent Hotel/Food expenses to the employees as incentives to be thrifty (Dunno if MS is one of them though.)

  8. Warll says:

    "You want to get off at the next stop, and then walk in that direction until you can’t understand the signs any more."

    Raymond of course never stopped walking and drowned in the bay.

  9. Carmen says:

    I remember that launch really well.  I was fortunate enough to get selected to represent Product Support at the launch event.  (There were only 2 of us.)  I remember walking up to Raymond and informing him that he had a cult following in the Product Support ranks because his stories, which prior to blogging, were kept on his private web server on the Microsoft corporate network.

    I became something of a hero in the support group when he actually mentioned it in one of his posts.  Microsoft is nothing if not a weird place.  Of course, now Raymond has siezed the opportunity to expand his cult dramatically…

  10. An Anonymous Government (non-American) Employee says:

    Ah, Windows 2000!  Still in use at my workplace today.  This post was sent to you care of a Windows 2000 Professional workstation.

    Don’t worry – the "Upgrade to XP" project is to to complete by Easter….

    (I wish I was joking!)

  11. Cory Foy says:

    @Gabe Actually, it’s pretty standard to share hotel rooms for large events. I worked in the Field Engineering group, and when we got together we often would share hotel rooms. Or something like the large internal conferences where you have thousands of people flying in to Seattle – pairing up cuts those costs nearly in half.

    And, if you didn’t stay on the ball and pick a pair, you better darn believe you’d be paired up with whomever also didn’t have a pair.

  12. Joe Bleau says:

    I still run win2k at home and at work.  (Looks like I’ll have to downgrade to XP to play with the visual studio express, which isn’t making me too happy.)  It’s been a really solid OS for me, without all visual distractions of XP and the laters versions.  Lean and mean indeed!

    [In retrospect, perhaps I shouldn’t have mentioned that it’s Windows 2000’s tenth birthday and just left it as a hidden tribute. -Raymond]
  13. scorpion007 says:

    @Joe Bleau, you can turn off the visual distractions, you know.

  14. Yuhong Bao says:

    Interestingly, 10 years after release is the point of the end of Extended Support in the Support Lifecycle (as defined back in 2004), and indeed after the July Patch Tuesday (which was modified from the end of June around the beginning of 2006, I think, to allow last security patches) of this year, Extended Support for Windows 2000 ends.

  15. Todd S. says:

    I have heard of the Microsoft practice of two people to a hotel room, and this seems to be a global rule; I first heard of it mentioned 10 years ago by employees of Microsoft Turkey.

  16. 10 years… they seemed less, I still used it on few older machines till last year. Great OS, rock solid, the only thing in which I really preferred XP over it was the shorter boot/resume time.

    The funny thing is that 2000, one of the best OSes Microsoft ever made, came out almost at the same time of that bunch of crap that was Windows ME. I still don’t understand why they decided to release yet another OS of the 9x family, after all 2000 didn’t miss any major feature of 9x (at least at API level, i.e. it wasn’t like NT 4 that didn’t had PnP/DirectX/…), and it was lightweight enough for the new machines of that period.

    I still have on my PC the customized Win2K ISO I made with SP4, IE6, DirectX 9, WMP 9, .NET 1.1 and a whole bunch of hotfixes (updated to September 2008, if I remember well); and nonetheless, it weighted just 386 MB.

    [ Raymond of course never stopped walking and drowned in the bay. ]

    In my opinion this deserves the magic "Raymond star". :)

  17. Ray Trent says:

    Am I the only one that initially read that as "Windows 2000 lurched into San Francisco"?

    (I’m guessing I caught the "grmgmergm…" out of the corner of my eye and it put me in the mind of Frankenstein’s monster).

  18. tsrblke says:

    @Raymond Comment:

    Someone would have figured it out eventually anyway.  We are geeks after all ;)

  19. Stephen Jones says:

    I used Windows 2000 for six years and only changed because I changed hardware. I’m still on XP and unlikely to change any time soon.

    Both Office 2000 and Windows 2000 were a great change on their predecessors (if you used other scripts than the Roman Script you would have realized the importance of Unicode in Office 2000). Since then all we’ve had are incremental improvements.

    Both of them more or less put to sleep the idea that Linux and the Mac OS were so much more stable. When Win 98 came out with the bug that it crashed if used continuously for 49 days various people offered a prize to those that could run it for 49 days without crashing beforehand (there were no takers).

    Win ME was a disaster. It came after in Win 98SP2 MS had actually produced a reasonably stable version of Windows, and everybody knew it was just a stopgap until MS sorted out the odd hardware incompatibility with W2000.

  20. Marc K says:

    When Windows 2000 came out, there was still plenty of software compatibility issues and horribly immature third party drivers.  ME was put out so that MS could continue its revenue stream without the compatibility headaches.  

  21. 2x millennium says:


  22. Stephen Jones says:

    —"ME was put out so that MS could continue its revenue stream without the compatibility headaches."—–

    But did MS get an extra revenue stream from ME. I know of nobody who upgraded to it. It could just have continued with 98SP2, which was a fairly stable release.  

  23. The Repair Man says:

    @Stephen Jones:

    By that time, MS had already locked OEMs in? I remember seeing quite a few new PCs coming with ME, although that might not be statistically significant sample.

  24. Brian K says:

    First off, Windows 2000 has been and still is a great workhorse for me. I have it on a development tower with some MPEG and encoder cards. It only seems obsolete for me for two reasons: 1) Can’t backup to Windows Home Server and 2) IE6. Oh one more thing. When driver issues occur, vendors don’t have a W2K system to try them on.

    Second, I once spent a night in Chinatown. I flew to San Franciso on an emergency trip to get a system running at a trade show at the Moscone Center. I dropped off my kids at a coworker’s, raced to the airport, flew to SF, cabbed over to the show floor, and got the system going. By this time it was getting late. I asked some "partners" about finding a place and they basically laughed and said "Ha – good luck this time of night". I called Holiday Inn and somehow found out the one in Chinatown had a room but it was the "small room by the elevator". I walked a few blocks and caught a cab over there. As I checked in the desk clerk said "Ah yes, we need to mention that its the small room by the elevator". I asked "Whats so special about this room, that I keep getting warned"? She said it was just that sometimes you can hear rumbling. "Fine", I said, and was glad to have it". The  room came with a free bottle of wine, so there’s where the other tie in to Raymond’s story comes in. Only the next morning did I fully grasp where I was. I didn’t fell so hot, but I did make it back to the show floor fairly early to make sure everything was OK. Back to the airport and back home I went. Crazy.

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