Here's my go to list. A mish mash of songs I like, songs with great production quality, and songs that have various elements which cover my typical musical tastes.
Dusty Springfield- Son of a preacher man
Bob Dylan- Tangled Up in Blue
Hall and Oates- She's gone
Dire Straits- So far away
Talking Heads- Naive Medley (This must be the place)
Genesis- Abacab
Rush- Tom Sawyer
Steely Dan- Hey Nineteen
Yello- Kiss in Blue
New Order- Blue Monday
Tool- Chocolate Chip Trip
Breakout- Swing Out Sister
Vail Johnson- Bass solo
Miles Davis- So What (from Kind of Blue)
Pharoah Sanders- Harvest Time
I usually judge my speakers based on a few key elements: 1) how "in control" the bass is- ie not boomy. 2.) Whether or not there is the right amount of bass. 3) Presence, sound stage and clarity of the highs (if I can close my eyes and see the actual cymbal being struck and know where it is in the room). 4) Presence of details (can I hear the sound of fingers on guitar strings, or hear a breath before a horn is played). 5) Smoothness of the vocals and horns (ie. the upper mids aren't annoying at higher volumes)