Nightline Playlist: Harry Connick Jr.

'Only the Lonely'

Connick considers the music legend Frank Sinatra "the best of all of the male singers."

"'Only the Lonely' is one of the great musical performances," he said. "The songwriting, the orchestrations, everything was perfect. As somebody who does that for a living, I can tell you it is extremely hard to do what he did, especially when you consider what came before him.

"I mean, I have a lot of information from which to draw," Connick said. "You know, he didn't -- and it's a great masterpiece."

'The Door'

"I had listened to George Jones, but I had never really ... gotten into him," said Connick. "And after I did, I was mesmerized. ... There's a song that he does called 'The Door' and it's incredible. I mean, I've listened to that song 1,000 times and I'm always hearing new things that he does.

"I mean, not to undermine his process, but it seems like there's almost no thought that goes into it," Connick said. "Yet clearly, there is."