The Osmonds star, 67, has shared introduced his new "co-star" for the remaining dates of his solo residency at Harrah's Las Vegas - an avatar of 14-year-old Donny.
In an Instagram video introducing AI Donny, he said: "I have a new co-star at my Las Vegas residency, and we are going to be making history together.
"Can you imagine sharing the stage with your 14-year-old-self?
"Well, it's happening, thanks to some mind-blowing AI and CGI technology, I'm going to be talking and singing with Donny Osmond, you know the one from 1972."
Osmond is then joined by the avatar and asks him: "What does it feel like to sing with yourself 50 years in the future?"
The young Osmond said it was like performing with his "grandpa".
Osmond says: "It's incredible. This is something you're not going to want to miss."
The Puppy Love hitmaker started his residency at Harrah's back in 2021 and it will wrap in June.
Speaking about the rise in the use of AI (artificial intelligence), Osmond previously told Fox News Digital: "AI is a tool, not a substitute.
"So, I love the prospects of AI. I love what it can do for me as a producer, as an artist – as a tool. And that's it."