With almost 100 albums and a career that's spanned more than half a century, Tony Bennett tells Rachael the secret to his lasting success. "The audience has been beautiful to me right through the years and I love what I'm doing," he says. "I always say, I never worked a day in my life because I sing and paint ... it's absolutely wonderful."

Tony brings Rachael one of his signed paintings, and proudly announces that eventually he's going to have four paintings in the Smithsonian. But if you can't make it to D.C., you can head to Bloomingdales in New York City where one of his winter paintings is adorning their holiday gift bags!

Fans of Tony's are in for another holiday treat this year -- his first Christmas album in 40 years. Rachael asks what made him finally decide to record A Swingin' Christmas after all this time. "My son Danny, who manages me, he came up with this idea," Tony explains. "He said, 'Why don't you do a swinging album so when people have parties, they can put that album on and have a nice spirit while the party's going on."

"I love to swing. I mean, in a good way!" Rachael jokes.

After taking a few audience questions (and confirming that he was once a singing waiter), Tony is joined by his daughter Antonia, who shares what Christmas was like growing up with her famous father. "My dad used to come and pick my sister and I up," she says, "and we would go over to Ella Fitzgerald's house every Christmas. We'd spend some time there and then we would go over to a great painter's house named David Hockney. Most of my Christmases growing up were like that."

Antonia joins her dad for a rendition of "I've Got My Love To Keep Me Warm," featured on Tony's holiday CD.