Every Generation Needs a Crooner...

Harry Nilsson was a crooner for a generation that turned their backs on the musical styling that their parents generation had grown up on. Nilsson took cues from some of the great voices before him, and with the revolution of singer/songwriters that were beginning to flood the airwaves, he managed to create his own style that was more indicative of the pop charts of the day.
An amazing singer/songwriter that had a vocal range that was uncommon in artists of that time. He was a studio musician through and through, but created some of the most profound recordings that showcased both his voice and his knack for arranging a song. This is headphone music at it's best.
There is often debate over who the "5th" Beatle was. I would say it is Harry Nilsson. His song writing and styling owes much to the ground that was broken by Rubber Soul, Revolver, and Sgt. Peppers. The Beatles decision to focus on albums rather than tour changed the face of what a singer/songwriters place was in pop music. This worked nicely for Nilsson, since he neither performed live, nor toured (nor id he want to). If you doubt the merits of the 5th Beatle argument than check out the Nilsson/Beatles medley "You Can't Do That." This is a great example of how good technology and talent can compliment each other.
Below is a nice clip, with bad syncing, of Nilsson performing live at a piano on The Smother's Brothers show.