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The song was originally a hit for the Drifters in 1962. There are numerous other versions so I will just point you here to do some digging: http://en.wikipedia.org/wiki/Up_on_the_Roof_%28song%29#Other_recordings
Eddie Holland sang "Jamie" in 1962
A song by 'Traffic' in 1967
Shelley Fabares-it reached number 0ne in 1962.
Ann-Margret sang at the Academy Awards presentation in 1962, singing the Oscar-nominated song "Bachelor in Paradise".