I just posted a Rory/Jess fanmix to sundry fan-mix sites. Since the mix is from Jess's POV, and he tends to be a bit laconic in my head, I'm putting my reasons for choosing the songs here. Also the songs themselves, in case any of y'all aren't actually a member of one of the fan-mix communities.
1. The Postal Service--Brand New Colony: It fits with the kind of misguided idealism that characterizes Jess. As a bonus, it features a line that always reminds me of Ayn Rand's Anthem and why it always annoys me. I think Jess might have a bone to pick with Rory over that book, but that's not a subject for a fanmix.
2. Air--You Make It Easy: Jess's slightly revisionist history of their relationship. He's done some rather underhanded things (I'm thinking the picnic basket, here) to get Rory's attention, after all.
3. Bright Eyes--Puella Quam Amo Est Pulchra: Because there's some deep-down insecurity hidden beneath the James Dean bravado.
4. Bruce Springsteen--Born to Run: More on the James Dean thing. This is the quintessential bad-boy song, and I don't think any of us can successfully argue that Jess is not that quintessential bad boy.
5. R.E.M.--At My Most Beautiful: Because he can be sweet, too. I think he really is someone who'd "save your messages, just to hear your voice."
6. The Offspring--I Want You Bad: Sometimes Rory's innocence gets on his nerves a little--specifically at that party, just before he and Dean have their...um...argument.
7. Gin Blossoms--Hey, Jealousy: Jess's brief return, which he spends constantly running away from Rory, all the while thinking about how he's screwed everything up.
8. Eve 6--Open Road Song: Immediately after the previous song, Jess finally confronts her, tells her he loves her, and then leaves. Cathartic as it might have been for some of us, I don't imagine Jess was terribly proud of himself, and the sneering bitterness of this song is what inspired this soundtrack from the start.
9. Jimmy Eat World--Work: The requisite "run away with me" song. Damn, but I would like to know what precipitated that frenzied little descent into irrationality.
10. Vertical Horizon--Best I Ever Had (Grey Sky Morning): I think most of this song could apply to Jess, but for him it all distills into one line: You don't need me back.
11. Tool--H.: Because we know Jess likes Tool (I can provide evidence if requested), and we know Rory's had a lasting effect on him. Now we know he couldn't have written the book without her.
12. Joni Mitchell--Both Sides Now: This was going to be on the soundtrack before Logan's snide comment about folk singers, but I just had to change the reasoning to reflect it. The original reasoning was something about how Rory makes him feel, knowing it's all cliche and not caring. It wound up much more succinct.
13. The Postal Service--Nothing Better: The closure song, because I highly doubt he's actually coming back to the show. Jess finally understands that he can't keep doing this over and over, not to himself and not to Rory.
And if you're interested:
Zip File! ...Now I have to go study for my French exam. Because I have an 89.7% in that class. *facepalm*