Quote Originally Posted by dfs View Post
That's tough enough right there. 40 of all time is beyond me.
I'll go for 25 song/performer combinations and let you decide what to cut.
I reserve the right to change all of these on reflection.
In rough chronology

The Band Played On - Tony Pastor
You're a grand old Flag - George Cohan
April Showers - Al Jolson
Brother can you Spare a Dime - Rudy Vallee
Happy Days are here again - Leo Reisman
In the Mood - Glen Miller
Don't Sit under the Apple Tree - The Andrew sisters
I'll be seeing you - Bing Crosby
Somewhere Over the Rainbow - Judy Garland
Hound Dog - Elvis Presley
Mr. Sandman - The Chordettes
Hello Dolly - Louis Armstrong
Night and Day - Ella Fitzgerald
Fly Me To the Moon - Frank Sinatra
The Good Life - Tony Bennett
A Hard Day's Night - Beatles
Feeling Groovy - Simon and Garfunkle
All along the watchtower - Hendrix
I can't get no Satisfaction - The Rolling Stones
Good Vibrations - The Beach Boys
Get Dancin - Disco Tex and the Sex-O-Lettes
We Will Rock You/We are the Champions Queen
You might Think I'm Crazy - The Cars
Walk This Way - Aerosmith and Run-DMC
Mysterious Ways - U2
Meant to say this too -- this is a pretty damn good list. A Hard Day's Night is probably the Beatles song I'd choose too. It's not my favorite, it's not their most creative, but it sounds SO DIFFERENT from anything else of its time. And the singing is perfect, perfect.