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

To Thom’s notion of hearing somethin new with repeated listening -
my picks both go there aggressively and don’t.

I was definitely thinking along those lines for my choices. The four guitarists I chose to bring along (Richard Thompson, Lindsey Buckingham, David Hidalgo, and Dave Edmunds) represent four very different aesthetics in their approach to the instrument. Because they all "look back" in different directions and also "point forward" in different directions, this group allows for great variety in contemplating why they’re doing what they’re doing - my version of Thom’s point.

OTOH, I’ve listened to these guys for so long that I’m sure I’ve covered a lot of what’s in there. (Not all, but a lot of it.) To really do what Thom suggests, you’d almost need to bring along great music that you haven’t spent a ton of time with. Great idea, but a Tricky task to actually pull off, IMO.

BTW, my last choice was great songs sung beautifully. For those rare moments when guitars aren’t the point.

One of many samples that comes to mind:

Box of The Haydn Piano Trios played by Beaux Arts Trio
Brahms: Symphony No. 3, cond. by Rudolf Kempe/Berlin Philharmonic
Brahms: Double Concerto. Heifetz/Piatigorsky/Wallenstein
Rachmaninoff: Symphony No. 2 cond. by Ormandy/Philadelphia Orch 
                                                     1975 complete version RCA
Dvorak: Symphony No. 8 cond. by Kertesz/London Symphony

1.  Rush - Power Windows
2.  Tears For Fears - Songs From The Big Chair
3.  Fleetwood Mac - Rumours
4.  The Beatles - Revolver
5.  The Beach Boys - Pet Sounds

No particular order:
pink floyd the wall
toto. Past to present 77-90
Queen a night at the opera
genesis a trick of the tail
Eagles hell frezzes over
bonus? Pulp different class

DID:

Pink Floyd - dark side
roxy music - Avalon
king crimpson - in the court of the 
miles davis - get up with it
steley dan - gold

here is your kicker:
steve miler - the joker

That's a good start