Don't make it too long - and it'd be cool if it could reflect a particular feeling, mood, or setting. I'll start out with one - not too sure of the flow or the diversity of the tracks, but it's a start.
Drink and be Wistful
1. Augustus - Parlour (www.augustusmusic.com - free downloads)
2. Led Zeppelin - Since I've Been Loving You
3. Radiohead - Talkshow Host
4. Third Eye Blind - In The Background
5. Pearl Jam - Light Years
6. Rob Dougan - Nothing at All
7. My Two Friends - Oceans (www.mytwofriends.com - download this song!)
8. Nancy Sinatra - Bang Bang (My Baby Shot Me Down)
9. Evanescence - My Immortal
10. Radiohead - Exit Music (For a Film)
11. Third Eye Blind - God of Wine
12. Robert Randolph and the Family Band - Smile (www.robertrandolph.net)
13. Coldplay - Everything's Not Lost
Where do I put this?
Billy Joel - Pianoman
Notes:
1. The reason I choose #1 is the lyrics - makes you just sit down, pour yourself a glass of scotch or bourbon, and just reflect on whatever's been going on recently.
2. #2 is just a great "I'm damn tired, it's late at night, and I need a drink" type of song.
3. I don't know if #3 should be in there, really.
4. #4/#5 need to go together, I feel - The Background gets kinda intense towards the end, and Light Years, although a strong song, kinda diffuses that intensity - perfect for the Rob Dougan song coming up.
5. At least one of #8-#10 could stand going, or at least be replaced. I can't think of anything for it so far.
6. Perhaps God of Wine should be moved higher up in the louder, more assertive songs.
7. I wanted to end on a bit of "good" wistfulness - you don't want to be drunk AND depressed. Both #12 and #13 are excellent choices for getting the job done, though I'm sure more are familiar with the Coldplay song. The Robert Randolph one is also stunning, though, so I put them both in.