I do better with albums or acts, songs just feels so arbitrary since there are so many of them. I'll keep it to one per artist and stick to rock/pop songs (no jazz) to make it simpler.
Bohemian Rhapsody- Queen
No Surprises- Radiohead
Strawberry Fields Forever- The Beatles
The Rain Song- Led Zeppelin
How Soon is Now- The Smiths
Gimme Shelter- The Rolling Stones
Beetlebum- Blur
Shangri-La- The Kinks
Teenage Dream- T-Rex
All the Young Dudes- Mott the Hoople
What would your jazz list be?
And cool to see T-Rex (& Mott the Hoople) on your list. I love glam/art rock 70's and Marc Bolan was such a great live presence.
I definitely like the Smiths as well. Morrissey & Marr were legends together - William It Was Really Nothing, Headmaster Ritual, Reel Around the Fountain, Bigmouth Strikes Again, the list goes on. Sometimes it is better a band does not get back together in some ways... right?
In addition to it being hard to compare it to rock/pop, Jazz is even more album centric, the songs are often so long, and are often covers of standards, so I don't even think of jazz artists in terms of songs at all, just albums. So for top ten Jazz albums I'd say-
1. My Favorite Things- John Coltrane
2. A Love Supreme- John Coltrane
3. Giant Steps- John Coltrane
4. Bitches Brew- Miles Davis
5. Kind of Blue- Miles Davis
6. Free Jazz- Ornette Coleman
7. Porgy & Bess- Miles Davis
8. Out to Lunch!- Eric Dolphy
9. The Shape of Jazz to Come- Ornette Coleman
10. Headhunters- Herbie Hancock
I'm a huge fan of the dramatic glam rock ballads, and those are my two favorites (even more than anything Bowie did like Life on Mars or Space Oddity) and I had to have a couple of them on there.
Agree on The Smiths. They definitely went out on top.