The Early Show co-anchor Julie Chen spoke with him after his big night in Washington earlier this month, and he marveled at how his career seems to center around bridges, and one in particular.
Chen noted that the 79-year-old Bennett got his start as a 10-year-old when little Anthony Bennedetto helped open the Triboro Bridge in New York City.
"Yeah," Bennett confirmed. "Mayor (Fiorello) LaGuardia, you know, he opened the bridge up. … And we walked across singing, marching along together.
"All of (the borough of) Queens marched over the bridge into New York City."
"So you remember that day well?" Chen asked.
"I'll never forget it," Bennett said. "There's something about bridges, you know. Between that and my signature song, '(I Left My Heart In) San Francisco,' with the Golden Gate Bridge. So there's two bridges in my life."
His life and career bridge generations, Chen said, from "The Perry Como Show" of the '50s to "The Simpsons" and MTV of today.
At 68, Bennett's "MTV Unplugged" CD won a Grammy for "Album of the Year."
"You know," Bennett said, "I learned from the masters. Sinatra. Just by staying with good songs … you have a — a marvelous career. Because you keep your integrity and you know that you didn't cheat the audience and you didn't pull anything over on them. You've given them the best that you can think of for them."
But it wasn't always glamorous. Bennett says he was once a singing waiter.
"I couldn't stand another job," he said. "And then I finally got a job as a singing waiter. And … that's where I said, 'I don't care if I make it or not. I'm going to do this for the rest of my life. I love to sing.'
"I would take their order for the meals that they wanted, and I would say, 'What song would you like me to sing?' And they would give me, you know, say, 'I'll Get By.' And I would run into the kitchen, and there were two Irish waiters there. And they were all excited about helping me out. And I'd say, 'What's the lyrics to "I'll Get By?" 'And they would tell me the lyrics and I would go right out and sing the song. I learned a lot of songs that way."
At the Kennedy Center ceremony, Bennett's friend, famed music producer Quincy Jones, called him "the soulful messenger of American songs; always has (been) and always will be."
And, while his voice has been the centerpiece of his fame, Bennett has also mastered a very different art.
"This year has been really fabulous," he told Chen. "The Smithsonian has accepted one of my paintings in there, which is — I've never dreamt of that in my life. I just love to paint. And I paint more than I sing, believe it or not."
And he sings a lot but, of all the songs he sings, he does admit to having a "favorite child."
"Do you ever get tired of singing 'I Left My Heart in San Francisco'?" Chen asked. "I mean, that is your signature song."
"This sounds terribly rude," Bennett said with a laugh, "but, do you get tired of making love?"
Chen said: "That answers that!"
"The Kennedy Center Honors" airs Tuesday at 9 p.m. eastern on CBS.
On Thursday, The Early Show catches up with another honoree from the class of 2005, Robert Redford.