I spent a night last week with my headphones on and listening to about 100 songs (skipping many), and here's what I came up with.
50. Fashionably Uninvited - Mellowdrone
Their are certain songs on this list that I remind me of the great tunes listened to at the Compound over the past decade, and this is one of them. Mellowdrone isn't the biggest thing since sliced bread or anything, but they have a few incredible songs. For now, I'm saying this is the best of the bunch.
49. Jesus, etc. - Wilco
Hearing the line "tall buildings shake, voices escape singing sad, sad songs" in the wake of 9/11 was probably one of the best lines about the tragedy in a song I've ever heard. However, seeing Wilco wrote this song before that awful event, it's not really about that, and that's what probably makes it so good. Shame on the cowboys who wrote their country songs exploiting that tragedy (it's Sunday morning as I'm typing this so judgment is fair game).
48. The Neighborhood #3 - The Arcade Fire
My favorite song from this over-dramatic outfit. It still always bothers me that it's the 3rd neighborhood but the 4th track on the album. This leads me to playing the improper song on the juke box often, leading to a bar full of hipsters having to listen to a very morose track #3. You don't want to see hipsters crying into their PBRs. That makes it even worse.
47. Kissing the Lipless - The Shins
WHOO! Something that always factors into how much I love a song, is if I've ever learned how to play it on guitar. I still play this one to this day, going on about 5 years now, so that's gotta count for something. Great lyrics too.
46. Off the Record - My Morning Jacket
I'm not giving extra points to songs that kicked ass live. When Jacket played this at the House of Blues I felt like I was at a Phish show in the 90s. That may sound uncertain to some, but seriously, comparing any live performance to Phish in the 90s is about the highest compliment you can give. Sadly, Phish will not be part of the countdown.