Before I get a bunch of argumentative, hateful internet comments i'll preface this with these words. These are not my absolute favorite songs, do I like them...sure, but the purpose of listening to these is my familiarity with how they sound on different systems and what each song highlights as far as audio reproduction is concerned.
In no particular order
1. David Gilmour-Wish you were here-Live in Gdansk. If you happen to be a pink floyd fan, I highly recommend picking up this blu ray, its very well recorded and has a lot of David Gilmour singing songs from his Pink Floyd days. This song in particular really highlights quite a bit of the spectrum, I typically listen specifically to hear the highs at 0:56 when the guitar comes in.
2. Dave Brubeck-Take Five. A classic, well-recorded song for the audiophile. I can't say i'd change anything about the way this song was recorded, and have listened to it enough times that I know how it should sound. Horns showoff mids, symbols throughout add some highs, and the subtlety of the drums, particularly during the solo, make this a test song anytime I design a new piece of audio equipment or change something in my setup. Bass heavy systems that aren't overly accurate really don't do the drums here justice.
3. CC Coletti-You Shook me. I got this song on an audiophile sampler from HDTRACKS.COM. Its really well recorded and neutral throughout. On a good system soundstage is what I listen for here. Really sounds like you're sitting in a studio with a bunch of musicians here rather than listening to a stereo or headphones.
4. Stevie Ray Vaughan-Tin Pan Alley. This song off of the Cold Shot album is probably the first I go to anytime I change something on my analog system. A great slow blues song driven mostly by guitar, Tin Pan Alley also features well recorded lyrics and crisp drum backing.
5. Flight Facilities and Christine Hoberg-Claire De Lune. This song has some great subtle bass that extends a little lower than most of the songs on this list. Vocals, strings, synthesizers, guitars, thumping bass...this song has a lot going on, An audio sampler platter if you will. Keep in mind...they do lead in and out with record player tracking sounds...its the song not your stereo.
Honorable Mention
Daft Punk-Something About Us. One of my favorite Daft Punk Tracks...and I have it on vinyl so its always been one I'll put on after making changes to the analog setup.