no three albums are that good to not eventually bore you after the gazillionth time.
that's always going to me my problem with questions like these. It's impossible to answer and rather pointless as well, because you would never be put in such a situation. It make a nice discussion topic I suppose.
Yeah, this sort of thread is always fascinating to work out your own answer and to see those of others. There are so many different strategies, and in different eras of my life I'd probably have chosen different ones. One is the runtime maximization strategy, where you pick box-sets, double and triple albums and such. Another is the hits strategy, where you choose best ofs and/or live albums. Another is the compilation or variety strategy, where you either pick various artist compilations or artists that are larger ensembles or highly multifaceted individuals who've covered a broad swathe of styles on a single album. There's the favorite album strategy, where you just figure out what your favorite three albums are and select those.
This time I just choose the "pick three niches you love strategy", historical and present, and the best representative of each. Ideally I'd have something more electronic, and at least something happier for a change, but with only three albums there's not much wiggle room, and I like melancholic music too much. Maybe I could have swapped out Chelsea for something like Bjork's greatest hits and touched on both more, but eh, I've been on a Wolfe high again that I've been riding a lot for the last few months. Somewhere maybe a decade ago there was a desert island disc thread, where you had 80 minutes to maximize the only music you'd have indefinitely, and that was fun to design as a compilation.