The Holidays, Country Style

Even if you aren't a big country music fan, it's hard to resist Kenny Rogers classics like "Lady," "Lucille" and "The Gambler." For nearly half a century, fans have been singing along with this country music legend—a singer and songwriter who's topped the charts with 22 number one hits and sold more than 100 million albums.

"I have to say, I love me some Kenny," Oprah says.

In 2008, Kenny will celebrate his 50th year in music, but he's not ready to fold 'em just yet. "We were talking about doing a farewell tour, [but] there's something so final about that," he says. "So we decided to do a 50-year anniversary [tour, and] call it 'the first 50 years.'"

Though he's sung some of his hits too many times to count, he says he never gets tired of singing the songs that helped make him a household name.

Watch Kenny sing two of his biggest hits!

"That's such great ammunition...when you go onstage to know no matter how badly I screw up in the first half, I've got 'The Gambler' and 'Lady' at the end," he says. "I told someone the other day that getting there is not as much fun as it used to be, but once I get there, there's no place in the world I'd rather be."