Let's get this party started...

Jesse Fuller - San Francisco Bay Blues
The Weavers - There's More Pretty Girls Than One
Ray Ellington - Long Black Nylons
Bobby Darin - Dream Lover
Townes Van Zandt - Why She's Acting This Way
NewGrange - Handsome Molly
Steve Young - Shopping For Dresses
War - The World Is A Ghetto
David Grisman, John Hartford & Mike Seeger - Maybelline
Jim Reeves - He'll Have To Go

And a non-random number for the folks in New York...

The Dixie Cups - Going To The Chapel