Entertainment Weekly.com has a great feature on its site right now: A list of 10 underrated Madonna tracks, which they describe as "unjustly ignored." Their list (in release order):
1. "Think of Me" from Madonna
2. "Over and Over" from Like a Virgin
3. "More" from I'm Breathless
4. "Waiting" from Erotica
5. "Bedtime Story" from Bedtime Stories
6. "Buenos Aires" from Evita
7. "Drowned World/Substitute For Love" from Ray of Light
8. "Shanti/Ashtangi" from Ray of Light
9. "I Deserve It" from Music
10. "Nobody Knows Me" from American Life
Here's my own take:
1. "Who's That Girl" from Who's That Girl (1987)
It was a #1 hit in 1987, but being left off of The Immaculate Collection means it remains undiscovered to new fans and virtually forgotten even by the old. This was the single that got me hooked on Madonna, and will always have a special place in my pop heart.
2. "Spotlight" from You Can Dance (1987)
Also released during my formative pop years, this great track failed to receive a proper single release. Too bad, it's great '80s dance, rivalling her best.
3. "Spanish Eyes" from Like a Prayer (1989)
This a dramatic, epic ballad, presumably about a woman watching her Spanish soldier/lover go off to war.
4. "What Can You Lose" from I'm Breathless (1990)
An arresting Madonna ballad and duet with Mandy Patinkin.
5. "Where Life Begins" from Erotica (1992)
It's very sexy, even dirty, but the seductive soundscape evokes "nighttime in the city" better than any Madonna track.
6. "You'll See" from Something to Remember (1995)
Since it wasn't on an album and got left off GHV2, this top 10 hit seems destined to be forgotten, which is a shame, since it is one of Madonna's all-time best ballads. Much better than "Take a Bow," which was her definining mid-'90s moment.
7. "Goodnight and Thank You" from Evita (1996)
A cheeky number chronicling Evita's bed-romping rise to the fame. Also features Antonio Banderas.
8. "To Have and Not to Hold" from Ray of Light (1998)
A moment of darkness from Madonna's late '90s electronic masterpiece. This is the perfect song for feeling brokenhearted vengeance.
9. "Time Stood Still" from The Next Best Thing (2000)
A great William Orbit ballad that got passed over for single release in favor of the tepid "American Pie" remake. A pity, this is a very beautiful song.
10. "Amazing" from Music (2000)
Sure it sounds like "Beautiful Stranger," but who cares? This was William Orbit's last good moment with Madonna before being discarded for Mirwais (who was subsequently discarded for Stuart Price--Oh Madonna, you really like Eva Peron in "Goodnight and Thank You.").