Top 5 Songs

1. Alex Chilton - The Replacements
2. Paranoid Android - Radiohead
3. Comfortably Numb - Pink Floyd
4. These Days - REM
5. Cream of Gold - Pavement
 
This is way harder than the Trolley Problem or picking your favorite child.

These might not even by my favorite songs by these artists on a given day, but it is an earnest attempt:

Long Tall Sally - Little Richard
Stand by Me - Ben E. King
Where Did Our Love Go? - the Supremes
God Only Knows - the Beach Boys
Sweet Jane - the Velvet Underground

Also, I’m picking recordings/performances and not strictly songs.

And this list is sorely lacking in Sam Cooke, Stax Records, and Punk Rock.