No, I don't have an iPod, but my birthday is in July (hint, hint).
Prefab Sprout: Jordan: The Comeback. Referencing Gershwin or Elvis in a song is dangerous, but Paddy McAloon pulls it off because he's that good. "Jordan" is nothing if not ambitious, about an hour long and made up of four themed sections. The second part is about Elvis (he faked his own death and is waiting for the right comeback song; he gets it, then promptly dies and goes to the moon to escape Col. Parker). The third is about girls (he's in favor of them, if a bit leery). And the fourth is about God, forgiveness, and reconciliation. See, I told you it was ambitious. Oh, and I have no idea what the first part of the album is about, though it seems to involve both girls and God.
Jane Siberry: When I Was a Boy. She's an odd one. Started out as a folkie. Went electronic for a while. Then came "The Walking," which fits no label, really. "When I Was a Boy" had the benefit of Brian Eno's production on a few cuts, and it has some of her best songs.
Matthew Sweet: Girlfriend. A power-pop masterpiece. Nothing he's done since then has come close.
Nilsson: Pandemonium Shadow Show/Aerial Ballet. If I could write songs, I'd write songs like Nilsson. (Or Paddy McAloon.)
The Beatles: 1. Yeah, you could make an argument for a number of Beatles albums, but, hey, all the hits are here.
Swan Dive: Circle. Terrific American pop duo from Nashville, for some mysterious reason more popular in Asia (they love 'em in Japan and Korea) than here. (For more info, see Swan Dive site on my list of links.)
Fountains of Wayne: Utopia Parkway. No one is putting out catchier pop songs these days. Who else could cover "...Baby One More Time" (on the "Out-of-State Plates" collection) and make it sound cool?
XTC: Apple Venus Vol. 1. Their oddest, and prettiest, collection of songs. Love the arrangements.
Nick Drake: Pink Moon. Yeah, depressing as hell, but beautiful.
Various artists: Pop Till You Drop Vol. 1
That last one is a show I put together for Theme Scheme Radio (see links at left). PTYD is the third wave of mixes I've done for myself or friends over the years. First came Radio From Hell. Not sure how many there were of these. They tended to feature very odd juxtapositions of songs. The second wave was Mood Music For Manic Depressives. Like Radio From Hell, MMFMD volumes were on cassettes, but they tended to have an upbeat side and a more melancholy side. Unfortunately, I had no tape-to-tape deck, so if I made them for friends, I don't have a copy.
Damn, I wish I had kept better records of what went on those things...
Oh, and that list is in no particular order and would probably feature at least 5 different entries if I did another list in a month.
Do share your own desert island disks in comments.