OK, so these aren't actually the 20 greatest singles of all time; they are more like "the 20 greatest singles that don't appear on albums I already own, or on albums that I plan to buy in the foreseeable future." But that's kind of wordy. The list almost reads like a sample of one-hit wonders, with some very obvious exceptions.
Some important caveats: potential songs had to be available through iTunes (believe it or not, four songs were forced off this list for that lone reason - it's 2008, people! Any song that was in rotation on MTV or radio should be on iTunes by now); the list is inevitably biased by my song-oriented listening patterns back in the 1980's and 90's, as opposed to the album-oriented listening of the past 10+ years; and rank is determined by the order in which songs were purchased (I bought roughly one per day) - kind of like a fantasy song draft.
And without further ado, here's the list.
1. It Takes Two - Rob Base & DJ E-Z Rock (1988)
2. Buffalo Stance - Cherry, Neneh (1989)
3. California Love (Single Remix) - 2Pac / Dr. Dre (1996)
4. Your Love - Outfield (1985)
5. Burning Down The House - Talking Heads (1983)
6. 867-5309 / Jenny - Tommy Tutone (1982)
7. So Alive - Love And Rockets (1989)
8. The Humpty Dance - Digital Underground (1990)
9. Natural Born Killaz - Dr. Dre / Ice Cube (1994)
10. Let's Go All The Way - Sly Fox (1986)
11. Talking In Your Sleep - Romantics (1983)
12. Wild Thing - Tone Loc (1989)
13. Don't You Want Me - Human League (1981)
14. Obsession - Animotion (1985)
15. Just Like Heaven - Cure (1987)
16. 6 Underground (Nellee Hooper Remix) - Sneaker Pimps (1996)
17. Push It - Salt-N-Pepa (1987)
18. Let The Music Play - Shannon (1983)
19. O.P.P. - Naughty By Nature (1991)
20. Supersonic - J.J. Fad (1988)