I could think about this all day and come up with a definitive list, but unfortunately I also have to work, so here's a quick list:
1950s: I've Got You Under My Skin: Frank Sinatra
I Walk The Line: Johnny Cash
1960s: Dear Prudence: The Beatles
Like A Rollin' Stone: Bob Dylan
1970s: Baker Street: Gerry Rafferty
Rock Ya Baby: George MacRae
1980s: Talk About the Passion: REM
And a Bang on the Ear: The Waterboys
http://www.youtube.com/watch?v=9SPsECHwsEw
1990s: Live Forever: Oasis
Across the Great Divide: Semisonic
2000s: Don't yet know