Regis Philbin has made a career out of talking, but at heart, he’s always been a crooner. Sitting on a patio at Beverly Hills’ Peninsula Hotel, he laughs at the fact his new Hollywood Records album, When You’re Smiling, comes out just 36 years and eight months after his Mercury Records debut, It’s Time for Regis! After a successful career as one of TV’s most popular personalities, host of one of the most renowned game shows in history and a best-selling author, he’s back to singing his favorites. Produced by singer in his own right Steve Tyrell, Regis covers songs made famous by Dean Martin, Fred Astaire, Louis Armstrong, Billie Holiday and Tony Bennett, and written by the likes of Irving Berlin and George and Ira Gershwin.

This album is in the tradition of smooth crooners like Bing Crosby, Fred Astaire, Dean Martin and Perry Como, who sang in their natural voices.
That’s what I was brought up on. And Bing Crosby was the first. He inspired all of those guys. Bing was the first time I had heard that kind of singing and it stayed with me my whole life.

What’s interesting about this album is, some of these songs go back to the ’20s and ’30s. You used a small ensemble in terms of the arrangements, though.
Steve Tyrell, who produced it, felt that was the way to do it for today’s audience. They arranged the rhythm section, then they laid in the soloists. That’s how it was brought to me, and I sang along to that. They added the strings after that.

This has to be the longest gap in history between a first and second album.
[Laughs]. 37 years!! It staggers the imagination. Frankly, I didn’t seek this. I don’t sing that much on the show. I do my little nightclub routine in Vegas and Atlantic City. Then, all of a sudden, out of the blue, here comes Hollywood Records’ Bob Cavallo with an offer.

Your first album, It’s Time for Regis!, was originally on Mercury.
PolyGram reissued it several years ago when they acquired Mercury. They changed my face on the cover so I look like Johnny Yune, the Korean comic. I don’t know how that happened. I don’t care, though, as long as they’re still playing it.

That first album came about after you sang "Pennies From Heaven" to Bing on The Joey Bishop Show, Oct. 25, 1967. He then returned the favor by singing "Too Ra Loo Ra Loo Ral" to you.
The very next day, Mercury offered me a recording contract.

"Pennies From Heaven" has a special meaning for you. You first sang it for your parents as a way of telling them you wanted to be a singer after they drove through a thunderstorm to visit you when you were graduating from Notre Dame.
My poor parents. They were sweating it out as to what I was going to do with my life. My father was Irish, she was Italian, it was New York City after the depression, and they worried. I rehearsed "Pennies From Heaven" in the music hall with a friend of mine for weeks. I sat them down, began to sing, and revealed that’s what I wanted to do for the rest of my life. Well, my poor mother started crying and my father was so angry, I thought he was going to take a swing at me. He was an old boxer, an ex-Marine. So I promised them I’d do something else. Which is how I became a television talker…

And your first job in show business was as a page for NBC at 30 Rock.
Worked with them all. I was a page boy for Steve Allen’s Tonight Show on the second balcony of the Hudson Theater on 44^th St., looking down on Steve Allen, Bill Dana, Steve and Eydie, Andy Williams, Louis Nye, Tom Poston… And I wondered, "What am I doing in this business? Look at all that talent." It was pretty scary. I didn’t know what I was talented enough to do. After seeing Jack Paar one night, I decided that’s what I wanted to be. A talk-show host. He wasn’t a stand-up comedian. He sat at his desk and told you a story about what he saw that day or that night. Tell you a little vignette about something that happened at home… And it was wonderful. I said to myself, "I could do that." And then this singing thing just happened.

You were the second banana to Joey Bishop on his ABC talk show.
Before that, I did my own Saturday night talk show live in San Diego on KGTV, a local NBC affiliate. That was around 1962. I booked the show and did the news during the week. And it was so successful, the suits from the Westinghouse network came down to see what it was all about. Zsa Zsa Gabor happened to my guest that night, and we had a rollicking interview. She went backstage and told the guys from Westinghouse, "He’s vunderful." And so, they tapped me in 1964 to replace Steve Allen, who had been doing a nationally syndicated late-night show for them in Hollywood, to go up against Johnny Carson. I was on for about six months, and then they replaced me. I started doing a talk show for local L.A. TV, with Joe Pyne as my guest. Joey Bishop happens to see the interview, and calls me to come see him the next day. I go to see him at the William Morris office, and he says to me, "You have a lot of talent." I said, "Really? What is my talent?" And he stood up, "I’ll tell you what your talent is…." And he paused: "You are a great listener." And we had three great years there…

Was music really your first choice? Would you have wanted to be a singer?
The way it turned out, I think I did the right thing by becoming a talker. I don’t think I have a great voice. I’m flattered that I made a couple of albums. It was a lot of fun and the reaction has been good. That’s all I really need.

What role does music have in your life?
It’s very important. I have a little boom box right in my office. Every morning before I get there, my assistant plays one of my huge selection of Dean Martin discs. It just gets me up, makes me feel good and gets me ready to do the show just like that. People ask how I can be so happy at 9 in the morning. When I hear those songs and those words, it just elevates me.

And obviously, you sing in your nightclub act.
Played the Playboy Club for a couple of months, several venues around town. I’ve opened for Steve & Eydie, Tony Bennett, Don Rickles… A little patter, a little song. Kathie Lee joined me and we became headliners. And after she left, I just continued. I’m doing Fox Woods in October, Atlantic City in November and Reno after that. And now, with this album, it should keep me going another 37 years.

Does Kelly Ripa sing?
She won’t do it. I said, it would be so great if you came with me. She’s funny, but she insists she can’t sing. She’s a little afraid of it. And it is scary.

All these songs have some meaning for you. Did you go back and listen to the originals before recording them?
Some of them, I did. I’ve been doing "You Make Me Feel So Young" in my own act. It’s a little like Sinatra’s version. But Bob Mann’s arrangement subdued it a bit, and I like that a lot. I love the way Dean did "I Can’t Give You Anything But Love." Louis Armstrong has done it. It’s a great old song. "It Had to Be You" is such a classic song. The lyrics are so beautiful and so meaningful. And people have been singing it since it came out in the ’20s. Bob Cavallo suggested I do "What’ll I Do." I was not that familiar with the song. I thought it came out pretty well. "You’re Nobody ‘Til Somebody Loves You" is another Dean Martin song. "They Can’t Take That Away From Me" I did as a duet with [my wife] Joy and she sounds real good on it. Originally, we recorded it as a demo to attract a famous female singer to do a duet, but she sounded so good that they decided to release it as is. She had never sung on record before. Like me, she had only sung for herself. But I knew she loved to sing.

What was it like working with Steve Tyrell?
I had seen him perform a few times at Feinstein’s at the Regency in New York. He would give you the background to each of the songs, and these were the ones he would sing. He has a great manner and fantastic voice. He’s a great entertainer. When it came time to decide on a producer, his name came up and I said, "I’m all for that, if you can get him…" And they did. He was a joy to work with, always optimistic, always up, but always wanting to get it "better!!" We did a lot of takes. I’m not used to singing that much. I would get a little hoarse, but he didn’t care.

Did you hear Fred Astaire songs like "Cheek to Cheek" in the movies first?
Of course. He was the best at delineating a song.

How about "The Very Thought of You"?
That was a Steve Tyrell choice. That’s a true love song, a great ballad. I didn’t think it was for me, but he made me do it, and I like the way it turned out. I had heard a great many different versions of the song.

What’s next for you?
I’m 36 years and eight months away from my next record. I really don’t know. Maybe it’s retirement… Did you ever think of that?

What drives Regis Philbin at an age most people are taking it easy?
After I finish the talk show at 10, I’m kind of free for the rest of the day. I get bored in the afternoons. This record was a lot more work then I thought it was going to be. There was a lot of pressure. You look through that glass and see that engineer who’s heard them all, and if there was something he heard that he liked, he would smile and encourage me. I’ve reached the top of my mountain a long time ago. A national talk show that people and see around the country.

What were the differences between recording 37 years ago and today?
The first album we did at United Recording Studios on Sunset Blvd. in L.A. I was scared to death. And there was a 22-piece band right in the studio, strings and everything. And they put me in a little booth, with me looking at them and them looking at me. And we recorded live. That was the finished product, unless you wanted to do it all over again. For this one, we had the rhythm tracks all laid down. It was altogether different. We did it at Deep Diner, a small recording facility in New York. We could add things after the fact, overdubbing a string part, a horn line, etc., which can be pretty grueling.

With this new career, is there any chance you’ll give up your day job?
Where am I going to go with this? This is for the people that remember this music. It’s a shame you don’t hear it on the radio anymore. I’m just trying to preserve the legacy of great words and great music. Which is tough, because it’s been inundated with the waves of the other stuff, which the kids really turn out to see.

There aren’t too many of the old style barroom crooners left.
Exactly. But the nice thing is, they took the time and laid it all down for us. It’s still there for us to listen to. That’s why this album means so much to me. There’s a sense of permanence about it.

But you’re a fan of modern pop music, aren’t you?
Absolutely. I have them on my show all the time… I know them all. Ja Rule, you name it.

What you need is a beef with a rapper to help promote the album.
Exactly. I think I’ll go right to the top. I’m going to call out Usher. When anyone comes on the show, I’m going to show them my album.

Do you still enjoy doing the show?
I enjoy it very much. I have a great venue. I have no writers, and 22 minutes to fill alone with my co-host. It’s quite a responsibility and a privilege. To say anything you want. To tell any story you have, whether it’s significant or not to anybody. And have fun with it. It’s an honor.