Counting

Zero - Smashing Pumpkins
One - Three Dog Night (or Aimee Mann's cover)
The Perfect Crime #2 - The Decemberists
Greek Number Three - They Might Be Giants
Four-Leaf Clover - Badly Drawn Boy
Take Five - Dave Brubeck
Streets of Sorrow / Birmingham Six - The Pogues
Seven Deadly Sins - Traveling Wilburys
Eight Days a Week - The Beatles
Grade 9 - Barenaked Ladies
Ten Dollar Solo - Stacy Shirk and Neil Patrick Harris
11:11 - Andrew Bird's Bowl of Fire
Rainy Day Women #12 & 35 - Bob Dylan
13th Floor/Growing old - Outkast
3.14 - Seatbelts
15 Petals - Elvis Costello
Sixteen Candles - The Crests
17 again - Eurythmics
18th Floor Balcony/It's Just Me - Blue October
19-2000 - Gorillaz
Feb 20, 2000 - Avett Brothers
One More Robot/Sympathy 3000-21 - The Flaming Lips
22 - Lily Allen
23 Hanachi - Soichiro Otsuka
24 - Jem
25 or 6 to 4 - Chicago

Damn, stuck.  I know I could keep going using google, but all of these came out of my library except for Sixteen Candles.  I had other options there too, but thought it was a good choice for the sake of variety.  25 seems a good place to stop anyways.