[Susan Roesgen, Cnn Anchor:] An historic space mission is on hold. Storms in Florida forced NASA to scrub this afternoon's scheduled launch of shuttle Discovery. They'll try again tomorrow. That is the news for now. I'm Susan Roesgen. "LARRY KING LIVE" is next.
[King:] Tonight, Michael Bolton. After selling more than 50 million records worldwide, "Desperate Housewives" Nicolette Sheridan's fiancee is stepping into Frank Sinatra's shoes. Also, an outrageous take on Brad Pitt, Angelina Jolie and Britney Spears from the one and only Cindy Adams, covering the rich, the famous and the infamous for more than 20 years. And then the world's most collected living artist Thomas Kinkaid. How the Painter of Light hooked up with the Points of Light Foundation. Plus, a multi-millionaire, after losing nine jobs in eight years, Steve Scott shares life changing lessons he learned from the richest man who ever lived. And singer Eric Bonet surviving a high profile marriage to Halle Berry and their even more public break-up. All that next on "
[Larry King Live". King:] It's a great pleasure to welcome to "LARRY KING LIVE," always great seeing him, Michael Bolton, the singer, songwriter, two- time Grammy winner. He has sold, by the way, over 52 million albums and singles. He has been accorded fame all over the world. And his newest album is "Bolton Swings Sinatra." There you see its cover. We have it here. "The Second Time Around" is the subtitle, one of, of course, the famous songs written by Sammy Cahn, which his fiancee Nicolette Sheridan sings with him. How did that come about to do a duet?
[Michael Bolton, Singer, Songwriter:] It's a great story. But it's just one of those kinds of miracle stories. Nicolette and I were together 14 years ago for about six years. And we'd just started seeing each other again. And I was putting together the songs for this "Bolton Swings Sinatra" record. And one of the song's I kept hearing was actually from a live recording from Frank in Sidney, Australia, the Sammy Cahn song "The Second Time Around." And, of course, the lyrics were about that second time and where you are in your life.
[King:] [Inaudible]
[Bolton:] [Inaudible] That's right. Well, you know this song. So I put it on. I was playing everything for Nicolette and saying what do you think? What do you think about this one? I love this one. And I'm not sure about this one. And I just dropped that on there. It was personal. And then, you know, Nicolette's always had a beautiful voice but been terrified to step up to the microphone. And she is basically a fearless person but singing is one of her deep fears.
[King:] Fears.
[Bolton:] So got her into the studio. She had to walk by we were in the Capitol Records Studio, the historic picture of Sinatra and Crosby on the wall and Judy Garland. And she had to pass these pictures of these icons and walk up to the microphone, terrified. Did a great job.
[King:] Why Sinatra? By Michael Bolton?
[Bolton:] It actually started as a swing record. It started as a big band swing record. That's what I really wanted to make. And I started listening to hundreds of songs and different versions, six, seven different versions of some of the greats. And of course, they've all been recorded by, you know, from Billy Holliday to Nat King Cole all the way through, you know, Tony Bennett, of course. And I just kept finding one important reoccurring theme and that was Sinatra's stamp on these songs. The ones that I wanted to record, Frank had delivered these incredible performances. And that is the reason why those specific performances are played on radio and TV everywhere around the world. If you're in Italy, Japan, wherever we travel, in the background all of a sudden Sinatra's voice will come on. And you'll actually you'll feel more at home. There is something familiar. There is something that makes you actually feel good about it. That's what endures. And so I decided this is what it is. It's "Bolton Swings Sinatra" record.
[King:] And of course, we have "You Go to my Head" and "Fly me to the Moon" and "For Once in my Life" and Summer Wind" and "Funny Valentine," "Got You Under my Skin," "That's Life." You do that up tempo?
[Bolton:] Yes. "That's Life" is...
[King:] "Second Time Around" with Nicolette, "The Girl from Ipanema," "Night and Day," "They Can't Take that Away from Me" and "New York, New York." What, Michael and you're a great singer.
[Bolton:] Thank you.
[King:] With enormous range and you can do incredible things with your voice? You do Opera.
[Bolton:] Yes. I love it all.
[King:] What did Sinatra have?
[Bolton:] [Laughing] Sinatra, besides amazing phrasing, he's a story teller. Sinatra would tell the Sinatra understood that composition's are the single most important thing for an artist. The way a great actor knows a great script is necessary, no matter how good you are as an actor. Sinatra would lead the lyrics and understand the intention of the composer. And then tell that story. And I think one of the elements that made Sinatra a great actor was what made him a great interpreter and great story teller. He also had beautiful tone. If you listen to his ballads, listen to "My Funny Valentine" and "The Wee Small Hours," you see this guy who everybody I know you spent time with him. You had this great interview with him. You probably did more than one. But one of the best was with the two of you. That he had this tough persona, this tough image. But what I heard while studying and listening to him was the most vulnerable human being at the microphone. That's when he was that's when he had the liberty, the permission to be that kid he was, the child he was, a single child.
[King:] So many facets to him.
[Bolton:] A multilayered guy.
[King:] Was it tough, therefore, to find, for you, singing his songs?
[Bolton:] You know, it was a challenge. I wouldn't call it intimidating but, you know, I've sung with Pavarotti, I've sung with Ray Charles, my great hero, mentor, you know, and you're nervous at first when you do that. But it's what you love to do. And they've picked this body of work, this material that spoke to them. And brought it to life. Here, you're walking into these enormous shoes, especially with songs like "New York, New York" and "That's Life." And you just have to bring something that you feel strongly to the microphone. Your job is to step up and hit it out of the park.
[King:] And you recorded in the same studio, at Capitol, where Frank recorded.
[Bolton:] Yes. We recorded where Frank did a lot of his records.
[King:] Was his shadow there?
[Bolton:] His shadow is everywhere. We were doing a couple of interviews there and we were talking about how large the Sinatra shadow looms basically everywhere. And the power went out during the interview.
[King:] [Laughing] Frank's there.
[Bolton:] You see what I'm saying? Those are big, giant shoes. His family's been great. His family's been I've sent them all records and I've spoken to Frank Jr. And I hope to work with him. He's a great arranger as well.
[King:] Michael Bolton is our guest, the great Michael Bolton. Over 52 million albums worldwide and the new one is "The Second Time Around, Bolton Swings Sinatra". Don't go away.