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

Richard Thompson - Two Letter Words
Fleetwood Mac - Say You Will
Los Lobos - How Will The Wolf Survive
Rosanne Cash - The List
Rockpile - Seconds of Pleasure

Id be pissed at myself pretty quickly, but that would be true of any five I chose.

Well, Thom, if we’re taking five guitars and/or amps instead of albums, I’ll play:

James Goodall Dreadnaught
Schroeder Chopper (LP style)
Tom Bills "Falling Leaf" archtop
Hughes & Kettner Grandmeister 36 amp
Fractal Axe effects processor

I’m borrowing your strings and plugging into your AC.

Note bene:

1) The H&K may not be the best sounding amp ever, but it is very good sounding and crazy versatile - pretty important for this particular gig, I’d say.

2) I don’t own the Fractal Axe system due to its complexity. However, I gotta figure that there’s gonna be sufficient time on the island to figure it out.

Thom,

Funny thing about Teles (and the variants thereon)...

I own several really outstanding boutique variations, but I end up playing my good old, modestly priced Fender American Standard (tho it's been modded with Barden pups) more than any of em.  If anyone can top the original tho, Jason might be the guy.  

Jason's take on the LP is IMO downright fantastic and his quirkier designs - including a variation of the Turner Model 1 - are pretty tempting.  He's an outstanding luthier for sure.

The other "go-to" in my electric collection is a Henman-Bevilacqua that combines a bolt-on neck and long scale with humbuckers to make a cool Gibson/Fender hybrid (definitely more Gibson flavored, tho).

if we get another couple of axes on our Island, the Fender and the H-B are coming along, for sure.

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.

PacMan,

Your selections bark up a very different tree than mine, but Tony, Toni, Tone is a great dark horse choice.  I'd probably choose "Sons of Soul", but "House" is an excellent album, too.  Raphael Saadiq is a generally overlooked talent, IMO.

Obligny,

That scenario represents a wonderful opportunity to learn to play the Ukulele!