You can only take 5 albums to a deserted Island...

Gotta have some variation for my 5:

1)  Pink Floyd - Dark Side of the Moon
2)  Norah Jones - Wish You Were Here
3)  Miles David - Kind of Blue
4)  Bach's Cello Suites - Janos Starker 
5)  AC/DC - Back in Black

Ginger and Mary Ann would improve this whole hypothetical scenario thing, as well!

If I was forced to grab 5 it wouldn't be something I know. I have those feelings and memories implanted. I think it would be some classical music I've only dip my toe into  and hope I chose wisely and I don't hate it. But just in case Id try and snatch a diamond of a Jerry Garcia Band show, and pray it wasn't a snoozy noodle fest.  He always played great covers of all kinds of essential stuff snd covered the gamut from ballads, jams from heaven, reggae, bluegrass, timeless Hunter-Garcia collaborations. Honestly though a desert island would be music enough, sweet sounds. If I was given a choice between music or a surfboard though that would be tough, but with push come to shove, no contest. I'd leave the classical and grab my 7'2 Pendoflex. 

Can the 5 be double albums?

Aerosmith - Get Your Wings
Black Sabbath - Master Of Reality
Lou Reed - Transformer
Neil Young - On The Beach
Pink Floyd - Animals

Kenny G: Forever You
John Tesh: At the Top
Gang Thugs 4-Ever: In It 2 Die (uuughh..yeah)
Celine Dion: Singing Higher Than You
Justin Bieber: Straight to Your Heart, Girl