5 albums, 5 songs. You'd get to bring both (so why would you bring a song on of the albums you've picked!)

ALBUMS
OK Computer (Deluxe Edition) - I am never sure if I like OK Computer
or Kid A more, but OK Computer I can listen to anytime, Kid
A requires a mood, thus OK Computer from my favorite band.

You're Living All Over Me - Amazing album, and even if I would only
really listen to "Tarpit" and "In a Jar" over and over a lot
of the time, it'd still be immensely worth having there.

Slanted and Enchanted (Sordid Sentinels Edition) - It's Pavement.
Crooked Rain is my favorite album in the original edition,
but Sordid Sentinels Edition has always beaten out LA's
Desert Origins Edition of Crooked Rain by a long shot for me
particularly for the Peel Sessions (Here Live), "Frontwards",
and "Shoot The Singer (One Sick Verse)"

The Name of This Band is Talking Heads (Deluxe Edition) - Best live
album of all time? Maybe. Best Talking Heads album to bring
with you to an island? Definitely. The deluxe edition
almost acts a best of for their first four (and best four)
albums, so I don't have to pick if I want "Once In A
Lifetime" or "Don't Worry About the Government"

Hissing Fauna, Are You The Destroyer - I need something to dance to!
I would need at least one album with parts I could groove to,
and an album with parts to groove to filled with passages on
loneliness and isolationism would be perfect on a deserted
island!

SONGS
Ms. Jackson - I will never stop singing along to this. Ever. Proof
of my love of this track is present on my Last.fm,
somewhere it shows that day I listened to it on repeat
30-some times in a row.

Echos Myron - Incredible song, as short as it is, I could not stop
loving it. I had a hard time choosing between Slanted
and Human Amusements for albums.

Crystal Cat - Not a classic, by any means, but it kicks fucking ass.

Smells Like Teen Spirit - No one has gotten closer to a perfect pop
song since, and not many people ever had before. Also,
it was released as a single two months after I was
born (to the day!)

God Only Knows - The closest anyone has gotten to a perfect pop song.