Numbered playlist

She's the One - Caribou
Two Points For Honesty - Guster
Halfway To A Threeway - Jim O'Rourke
4th Time Around - Bob Dylan
Five Ten Fiftyfold - Cocteau Twins
From A Motel 6 - Yo La Tengo
Schottkey 7th Path - Aphex Twin
8 Ball - Underworld
#9 Dream (from Walls and Bridges) - John Lennon
Number Ten - Casiotone For The Painfully Alone
Eleven Twelve - Braces Tower
Rainy Day Woman #12 & 35 - Bob Dylan
Thirteen - Elliott Smith
14 Cheerleader Coldfront - Guided By Voices
15 Step - Radiohead
Sixteen Maybe Less - Iron & Wine
Anthems for a Seventeen Year-Old Girl - Broken Social Scene
18 Sekúndur Fyrir Sólarupprás - Sigur Rós
The Density of the 19th Century - Vijay Iyer & Mike Ladd
kiwi maddog 20/20 - Elliott Smith

Meme via pyrop, except I ignored the original restriction stating that the number had to occur at the beginning of the title. (otherwise I wouldn't have been able to get past 9!)