For me, it often becomes an argument that looks something like this:
Me: "I can't do it. I can't pick 5."
Excitable Person (henceforth EP): "You HAVE to! Or you'll DIE."
Me: "Pretty sure I won't die in an imaginary situation. And if I was really on a deserted island, then I likely would die due to starvation, dehydration... the albums have nothing to do with it."
EP: "Just pick 5 albums, damn you."
Me: "Ok, um... Zeppelin II, and maybe IV... Deftones' Adrenaline. Wait, wait, Deftones' Diamond Eyes. Wait, no. White Pony? Ugh. Fleetwood Mac's Rumours. A Perfect Circle's Thirteenth Step. Radiohead's... aw crap, can I have ten? I need ten. I haven't even gotten started. No, I need twenty. Twenty albums."
EP: "YOU'RE A TERRIBLE PERSON WHO CAN'T PLAY GAMES PROPERLY!"
Yep, it's true. I can't play that game. I refuse. My cop-out answer is that I would make 5 mixed cd's (yes, compact discs) in preparation for impending desertion on an imaginary island. And really, if I had the foresight to pack specific albums because I knew I was going to crash, I would just not board that plane. I watched all 6 seasons of Lost. I know how it works.
When it comes to choosing favourite albums, songs, or artists, it's like choosing a favourite child. Except that while you're choosing said child, you suddenly remember all the other favourite children you've had over the years and have to add them to the list (man, you've been busy). It can't be done. I am of the opinion that any true music obsessor can't whittle down their favourites to a mere few. Sure, I have some select go-to picks that will always be my favourite, but what about the album I can't stop listening to right now? Or the one I loved most when I was 12, but re-visit every year and play over and over for nostalgia's sake? I would need them all.
But maybe I'm alone in this. Judging by other peoples' reactions when I refuse to play this "what if" game, it's entirely possible that I'm just a stubborn jerk and everyone else is fully capable of answering. So I ask you:
If you were about to be stranded on a deserted island (and somehow knew about it in advance, yet still allowed it to happen because you make bad life decisions. I won't judge.), what 5 albums would you bring?