Some more good contenders...

Saddest: "Most Of The Time" (Dylan)

Most Optimistic: "Piney Wood Hills" "Indian Cowboy In The Rodeo" "Native North American Child" "Sweet Little Vera" "He's A Pretty Good Man If You Ask Me" "97 Men/Don't Call Me Honey" (all by Buffy Sainte-Marie)

And "Oh Boy" by Buddy Holly.

How about that Buffy, eh?

- LH