Slackware back when it was the only game in town, then RedHat, then Debian, then GenToo, then Ubuntu (Xubuntu).
I tend to stick to one distro until the irritation level is high enough that it's worth the pain of trying out a new distro. If you say "What irritation level?" I will shake my head. All distros have a certain amount of niggle and not-quite-perfect-ness. One chooses to put up with the little irritations because the plusses are worth it. Until they aren't.
I moved from Slackware to RedHat because it had an actual packaging system. I moved from RedHat to Debian because of quality control issues, and because Debian you could actually upgrade instead of having to re-install every time a new version came out, and because of the huge number of packages; no more rpm dependency hell. I moved from Debian to GenToo because I was sick of being five versions behind everything, because with GenToo it was trivial to build a custom kernel (which I needed at that point to support certain hardware) and because I could get rid of all the cruft like KDE and Gnome support. And because it not only had just as many packages as Debian, but if you wanted to install something that wasn't in the distro, it could be added to the packaging system, rather than be a second-class citizen. I ended up learning a heck of a lot using it, so that was a plus, too. I moved from GenToo to Xubuntu because I was sick of recompiling everything. The amount of work needed to maintain the system was notably higher, and I wanted to relax for a while and have something that Just Worked. And being Debian-based, it also had a lot of packages.
A friend at work is trying to persuade me to move to Arch, but I haven't tried it yet.
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I tend to stick to one distro until the irritation level is high enough that it's worth the pain of trying out a new distro. If you say "What irritation level?" I will shake my head. All distros have a certain amount of niggle and not-quite-perfect-ness. One chooses to put up with the little irritations because the plusses are worth it. Until they aren't.
I moved from Slackware to RedHat because it had an actual packaging system.
I moved from RedHat to Debian because of quality control issues, and because Debian you could actually upgrade instead of having to re-install every time a new version came out, and because of the huge number of packages; no more rpm dependency hell.
I moved from Debian to GenToo because I was sick of being five versions behind everything, because with GenToo it was trivial to build a custom kernel (which I needed at that point to support certain hardware) and because I could get rid of all the cruft like KDE and Gnome support. And because it not only had just as many packages as Debian, but if you wanted to install something that wasn't in the distro, it could be added to the packaging system, rather than be a second-class citizen. I ended up learning a heck of a lot using it, so that was a plus, too.
I moved from GenToo to Xubuntu because I was sick of recompiling everything. The amount of work needed to maintain the system was notably higher, and I wanted to relax for a while and have something that Just Worked. And being Debian-based, it also had a lot of packages.
A friend at work is trying to persuade me to move to Arch, but I haven't tried it yet.