The top 10 is always a fun exercise. I pretty much slowed down listening to new music in the mid 90s, and quit almost altogether in the early 2000s (when I had kids).
After many, many years thinking through this, I decided a while ago there are only six records I am willing to put on anytime, anywhere -- records I've never once gotten tired of and still look forward to playing:
Gang of Four -- Entertainment!
Nirvana -- Nevermind
New Order -- Power, Corruption and Lies
Husker Du -- New Day Rising
Liz Phair -- Exile in Guyville
The Who -- Quadrophenia
There's another 30 or 40 records that might cycle through the bottom four depending on my mood. Right now I'm on an early 90s Chapel Hill, North Carolina kick (Superchunk, Archers of Loaf). Next month it might be Public Enemy or Brian Eno or LCD Soundsystem or Sonic Youth.