He and his sister, Marie, "have a show at the Flamingo in Las Vegas, and we do a meet and greet afterward, and this little 10-year-old boy who had seen me on Dancing With the Stars came up, and as he got closer and closer to the front of the line you could see him getting more excited, and when I met him, he said, 'Mr. Osmond, I didn't know you could sing, too,' " Osmond recounted, laughing.
The show he's bringing to Shippensburg is "different than anything I've ever done," he said.
A question-and-answer period lets audience members ask him about songs he has done. Then, he performs them.
"If someone asks for a song - boom - we're doing it," Osmond said.
The show is possible because of technology, which allows him to bring his vast catalog and repertoire of music and video clips.
"I'll actually have all the videos, the music. The other night, someone asked about the video I did with 'Weird Al' Yankovic, 'White and Nerdy,' and - boom - we had it up on the screen," he said.
"This is fun for me as an entertainer. I like to do things that haven't been done before, something that challenges me," he said.
After a short stint on Broadway in the early 1980s, his then-manager devised a plan for Osmond to shed his good-boy image.
"There was this whole plan for me to get busted for drugs," he explained. "It would have worked, too. We were going to go through an airport, have my baggage searched. It would have made headlines, but it would have been horrendous. I'd still be dealing with the fallout. I'd still be living it down."
Unlike other child celebrities, whose larger-than-life sex, drug, and alcohol scandals often draw more attention than the movies or records they make, Osmond, 53, chose to model his career after stars such as Elvis Presley and Frank Sinatra.
"They stuck to their music. There are not a lot of stars. It's easy to become a celebrity, but it's not easy to become a star," he said.