Let's just think what this means: a grown man went on live radio in front of millions of listeners and uber-seriously attempted and failed terribly to sing a song which 30 years ago was already cheesy lounge act fodder which was the punchline to lounge-lizard jokes. It was so wretched, and the attempt was so important to him (imagine him practicing and practicing with his home karaoke machine in his empty, sterile, lifeless apartment), that I was actually embarrassed and saddened by it. It was soooo bad, and yet George inexplicably obviously thought he was soooo good at it, that he used it to try to impress the C2C audience with his swingin', sexy pipes. Yeah, baby.
What it means is that George is horrendously out of touch with ordinary human emotions and understanding. Simple George doesn't get how ordinary people operate, how they feel, what they think. He lives encased in a plastic cocoon, shut away from real human emotion but self-deceived into believing he makes real human connections with his radio listeners. It's just sad.