Stand By Me--the "Playing for Change" musicians. This was an extremely good documentary with musicians all around the world playing and singing and the songs and video spliced together.
Leonard Cohen: Everybody Knows. This one features clips from the old Man from Uncle TV series and even has a small walk-on by a pre-Spock Leonard Nimoy.
David Bromberg's version of Bojangles Live, includes funny story about Jerry Jeff Walker.
I also love Bromberg's rather raunchy version of Kansas City, which is apparently no longer available on Youtube (except for a pretty crappy version someone uploaded).
Stop in the Name of Love by Jonell Mosser (I thought the Hope Floats movie was a little slow, but like the soundtrack).
The Blasters: I'm Shakin' (Rockabilly)
Lucinda Williams "I Envy The Wind" on the Essence CD is haunting and heart-breaking, but there are no good Youtube versions that I've found--poor sound quality on the live performances.
Kate Rusby: You Belong To Me (I think Patsy Cline would like this version too.)
Of course just about anything by the late, great Sam Cooke. Favorite is Live at the Harlem Square Club. I do not advise listening to the Live at the Copa CD, unless you want to see the contrast between the Black and White audiences in pre-Civil Rights Era America. For such a short career he has an impressive body of work--taken from this world far too soon.
Sam Cooke: Bring it on Home (I love when the guy in the audience shouts out "Hello!" & Sam almost loses it!)
Sam Cooke: Little Red Rooster (a little more "pop" than Howlin' Wolf's version, but features Billy Preston on Organ and Ray Charles on Piano)
Best palindrome ever: "Dammit I'm mad"