The "Alright seriously, i know you love radiohead but..." set

The albums:

OK Computer by Radiohead
OK Computer by Radiohead
OK Computer by Radiohead

The reason:

I know that plenty of my friends might actually think of doing this. But seriously guys, it's not the only album in existence. I know its good... but it's not that good. Get over it.

The "Understand the joke" set

The Albums:

Bad by Michael Jackson
Even Worse by Weird Al Yankovic
A Day Without Rain by Enya

The Reason:

If you're going to be stuck on a desert island you're going to want to laugh. So of course you have to bring Weird Al Yankovic's priceless work "Even Worse." But just to make sure you remember why the joke is funny you better bring Michael Jackson's Bad so you can fully understand the parody.

Enya is thrown in because you have to have some serious music so you can find the funny music even funnier.

The "Nuances of Grunge" set

The Albums:

Nevermind by Nirvana
Ten by Pearl Jam
Superunknown by Soundgarden

The reason:

If you're going to be stuck on a desert island for the rest of your life you might as well solve a very deep argument about grunge rock. With all the time in the world on your hands you will be able to listen to these albums over and over again and be finally able to answer the question "Who is better... Nirvana or Pearl Jam?" And since there are three albums I threw in Soundgarden too just in case you decided that for some reason they're better or if you'd like to keep reminding yourself why Pearl Jam and Nirvana are so much better.

The "Reminding You of Your Situation" set

The albums:

This Desert Life by the Counting Crows
Help! by The Beatles
Island in the Sun by Harry Belafonte

The reason:

If you're going to be spending the rest of your life on a desert island you might as well embrace it. And what better way to embrace that fact than by listening to music that reminds you everyday what you're going through. Put on This Desert Life when you want your desert island existence to feel like a sitcom, Help! when you genuinely think that people might save you at some point in the future, and Harry Belafonte when you want emerse yourself in your own personal island in the sun. These feel good albums make the lonely lonely existence somewhat laughable and livable.