to do then now would be retro, to do then then was very nowtro
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Operating Systems

Operating Systems bitprophet has used:

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1986
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System 6
Mac OS ("Classic")
MS-DOS
Windows 3.1
System 7
Windows 95
Windows 98
Microsoft Windows
Linux
Red Hat Linux
Slackware
Windows 2000
Windows Me
Debian
Windows XP
Mac OS X v10.2 (Jaguar)
Arch Linux
BeOS
NetBSD
FreeBSD
Berkeley Software Distribution
Mac OS X v10.3 (Panther)
OpenBSD
Mac OS X
Mac OS X v10.4 (Tiger)
Red Hat Enterprise Linux
Ubuntu
Mac OS X v10.5 (Leopard)
Mac OS X v10.6 (Snow Leopard)
Windows 7
Mac OS X v10.7 (Lion)
System 6
1986–2001
Came on the Mac SE which was my family's first real computer. Saw significantly less use once we got a Performa in the mid 90s, but was still used reasonably often till I got my own PC for college. Though in the later few years it was mostly for nostalgia...
Mac OS ("Classic")
1986–1999
MS-DOS
1990–
Never owned my own MS-DOS-only PC, but used friends' systems a lot as a child. These days it's limited to a ~quarterly foray into some WinXP system's command prompt...
Windows 3.1
1993–2001
Used sparingly on other peoples' computers until I was given a badass early 90s era Dell laptop by a neighbor going through his tech trash in 2001. Used Win 3.1 on that for about a half hour, then promptly overwrote it with a really old Slackware build.
System 7
1995–1999
Used on family Performa, which was the first and last color Mac we owned until I brought the family back into the Mac fold in the mid 2000s.
Windows 95
1997–1999
Was the first OS on my parents' first PC, a Dell of some kind in the late 90s that was eventually upgraded to Win98.
Windows 98
1999–2001
Made Win95 look terrible, and made it pretty easy to resist upgrading during WinME and WinXP's early days. Easily the best non-NT-based Windows. (This is like saying someone is "the nicest asshole ever!" -- but still.)
Microsoft Windows
1999–
Can't escape using this jerk as a gaming platform until all game companies are as dual-platform-friendly as Blizzard is. Or until Apple puts out more-customizable towers. (Or until the XBox supports mice, keyboards and user mods...)
Linux
2000–
Red Hat Linux
2001
Brief dalliance personally: first OS installed on my Linux test box. Was rooted literally overnight while plugged into UMass campus network. Wiped, replaced with Debian. This is an apt analogy for my attitude towards the two distro families since. Also used professionally for a short while -- was used as the file server for sharing a VB5/6 binary with a Windows network. No, it didn't make sense to me either, even at the time.
Slackware
2001
Largely limited to experimentation when getting used to Linux overall, and some unrelated experimentation when trying to find Linux variants that would run on a 386/SX with 4MB RAM and no CD-ROM drive...and that turned out to be Slackware 3.x!
Windows 2000
2001–2005
Never really used it myself per se, but recommended it for family/friends on older hardware that couldn't handle XP.
Windows Me
2001
Came preinstalled on my first personally-owned PC; wasn't savvy enough to use Linux desktop at the time; XP wasn't easily available to me yet. Such is the depths of my shame.
Debian
2001–
The king of Linux distributions! Have used it or derivatives thereof on and off since the start of my Unix career. These days I favor its child Ubuntu, but still use it on occasion when a client requests it specifically.
Windows XP
2001–2011
Main OS in the years between ME and my move to Linux full-time; ran my dedicated gaming PCs after I moved to OS X. Kept using it through Vista and into the early Win7 days because, well, why upgrade? Also useful on VMs in environments where one needs Windows software like IE, Exchange or WinOffice.
Mac OS X v10.2 (Jaguar)
2002–2003
First OS X I ever used. Can't believe how crappy it looks now. Was a breath of fresh air from desktop Linux in its era, however, given that it was the first to hint at the coming greatness OS X was to enjoy afterwards.
Arch Linux
2002–2009
Ran it on the desktop on and off during my Linux desktop days, and on the server when I still ran servers in-house (again, intermittently mixed with other server distros.) Lovely mix of spartan base install & near-upstream package layouts, compiled for modern hardware by default (back when this even mattered) but with a very easy custom-build system, and a decent package manager & rolling release system. I often describe it as the love child of Slackware, Debian and Gentoo.
BeOS
2002–2003
Once I moved on to desktop Linux on my main PC, my spare PC got to explore even more esoteric lands, such as QNX and BeOS. BeOS was really neat! I'm sad it (BeOS, not the PC) died.
NetBSD
2002
Limited use on an old laptop which eventually ended up using Slackware 3.x. It did work at least partially on the system (a 386/SX with 4 MB RAM), mostly proving the old adage about it running damn near anywhere.
FreeBSD
2002–2005
Have tinkered with FBSD for very limited periods throughout the mid 2000s. Definitely the most desktop friendly of the BSD family.
Berkeley Software Distribution
2003–2006
Have played with FreeBSD on and off; used OpenBSD seriously for firewall and server use, but got sick of its Spartan feel and lack of packages/support/etc found in the Linux world. Felt the security/purity wasn't worth the convenience tradeoff. Still have serious respect for the family, however.
Mac OS X v10.3 (Panther)
2003–2005
Ran this sucker on a Frankenstein of a beige G3 (made out of parts from 2 other beige G3s!) as well as a B&W tower, and then one of the gray-themed towers. It got me from my oldest/poorest used Macs up to the time that I bought a brand new Mac in the early 10.4 days. Expose was amazing!
OpenBSD
2003–2006
Firewall usage as well as a year or two of Web server usage. Secure as all get out, but with the expected usage trade-off in terms of easily available packages, community documentation, etc. Still, it had a very well engineered feel that Linux continues to lack to some degree.
Mac OS X
2003–
First introduced when working UMass OIT tech support, where each workstation had a Mac and a PC. Stole me away from desktop Linux when I realized I could have a Unix base and a no-bullshit-needed user layer.
Mac OS X v10.4 (Tiger)
2006–2008
Probably the OS X release I've used the longest overall thus far, seeing as it came out around when I bought my first non-used Mac, and I resisted the Leopard upgrade for as long as I could.
Red Hat Enterprise Linux
2007–
The bane of my existence, insofar as any Linux can be so. Stuck with supporting it part or full time depending on current job & whether they use managed hardware (whose hosts almost always prefer RHEL/CentOS) or cloud computing (where there's usually more flexibility).
Ubuntu
2007–
Moved to Ubuntu Server after my Gentoo server days (mostly effected by a job switch), but in a way it was a relaunch of my love affair with Debian proper that had begun in 2001. I still find it the "best" server OS, marrying the best things about Debian with a set of newer packages and some other conveniences.
Mac OS X v10.5 (Leopard)
2008–2010
Takes OS X 10.4 and adds even more awesome. Not much more to say. Was the first OS X where I felt serious pain (re: features and third party app availability) by being stuck on the previous version, especially at my job.
Mac OS X v10.6 (Snow Leopard)
2010–2011
Bog standard OS X upgrade, more polished than Leopard and nigh required once certain daily-use apps stopped working as well on 10.5
Windows 7
2011–
Finally upgraded to this sucker on my gaming PC and actually pretty happy I did so, it doesn't suck nearly as bad as Vista, doesn't look quite as ugly as XP, and of course supports modern and forward looking tech/hardware/etc.
Mac OS X v10.7 (Lion)
2011–
It's OS X, nuff said. Still on this guy, not upgrading to Mountain Lion until (as usual) most of my daily-use apps stop supporting Lion.