Here's a few more that I really like (there are some oldies and some "newer" songs).
Smashing Pumpkins - Thirty Three (really pretty song)http://www.youtube.com/watch?v=Xc9ZbS4KMdg
Gonna jump around through the timeline here. My taste in music has a lot of old school stuff - influenced by my parents. A lot of the oldies I like are things they listened to when they were young. Call it parental influence or w/e, but I like old school things.
Marvin Gaye - What's Going Onhttp://www.youtube.com/watch?v=rD78i6eoGkM
Someone put together that video based on things that were going on around the time Marvin Gaye released that song. I thought it was a nice video.
Moon River (composed by Henry Mancini) - Theme from Breakfast at Tiffany'shttp://www.youtube.com/watch?v=TvBGF7W4ALQ
The Doors - Break On Throughhttp://www.youtube.com/watch?v=tah0OnS3nBU
Nat King Cole - Unforgettablehttp://www.youtube.com/watch?v=q8tRTZIx298
Heart - Barracudahttp://www.youtube.com/watch?v=hpkitLUbeEg
And something more "current" I guess. I can really relate to this song at times, but it's probably not "legendary" to everyone and that's fine.
Sia - Breathe Mehttp://www.youtube.com/watch?v=U6PGrub3jUc