Some stars spend their careers protecting the version of themselves that first made them famous. Donny Osmond took the opposite path. He built a career by evolving with the times and then kept going. Today, in his Las Vegas residency at Harrah’s, the legendary entertainer performs a duet with a digital version of his 14-year-old self, the same teenage Donny who captured hearts decades ago with hits like “Puppy Love.”

The moment feels almost surreal on stage. Yet it also reflects something deeper about Osmond’s career. Instead of resisting technology or relying only on nostalgia, he has embraced new tools that allow him to reinterpret his own history in front of a live audience. That willingness to experiment with technology has helped him remain relevant for more than six decades in entertainment.

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Why Donny Osmond still connects with audiences

There is a reason Donny Osmond still matters to multiple generations. Older fans know the teen idol who broke out with songs like “Puppy Love.” Others know him from Donny & Marie. Theater fans remember “Joseph and the Amazing Technicolor Dreamcoat.” Younger audiences may know him as the singing voice of Captain Shang in Disney’s “Mulan.” Then there are reality TV fans who saw him win Dancing With the Stars or meet him again on The Masked Singer.

That range gives him something rare in entertainment. He does not belong to just one era. He belongs to several. And instead of resisting that, he leans into it. Technology now plays a role in that connection as well.

How Donny Osmond brought his younger self back to the stage

Osmond explained the idea when he sat down with me for my “Beyond Connected” podcast. The concept actually began decades ago when he started imagining what future technology might make possible. “Even when I was a teenager, I thought someday there’s going to be technology where John Wayne could be Obi-Wan Kenobi. And I was right!” Osmond said.

That long-held fascination eventually led him to a simple question. “Why can’t I sing ‘Puppy Love’ with my 14-year-old self on stage?” Osmond said. The answer involved combining several forms of digital production, AI modeling and stage design.

“The face is actually my 14-year-old face taken from pictures, the voice is my voice from interviews when I was 14, and the body is my 14-year-old grandson,” Osmond said. The result is a performance where two versions of Donny Osmond appear to share the stage at the same time.

It is not a hologram, it is something called a hollow box

Many people assume the younger Donny is a hologram. Osmond said that is not the case. “It’s not a projection, like a laser projection. It’s not like a hologram. It’s a totally different technology,” Osmond explained.

Instead, the illusion relies on a piece of stage technology known as a hollow box. The structure is built into the set and designed to look like a vintage recording booth on stage. Inside that space, advanced visual systems combine CGI, AI modeling and stage lighting to create the digital image of the younger Donny so it appears full-size and three-dimensional.

The effect blends archived photos, computer-generated animation and voice samples from Osmond’s early interviews to recreate his teenage likeness. His grandson provides the physical body movement used to animate the performance. Standing just inches away from the illusion, Osmond can look directly at his younger self while singing. From the audience’s perspective, it appears as if the two performers are sharing the stage face-to-face in real time.

Even after performing the sequence night after night, Osmond said the experience still surprises him. “I do it every night, and it never gets old. It’s like looking in the mirror 54 years ago,” Osmond said. For longtime fans, the moment connects the teenage star they remember with the seasoned performer he is today. The visual contrast tells the story of a career that has spanned generations.

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Donny Osmond has always been fascinated with technology

One of the most surprising parts of my conversation with Donny is that he does not sound like a celebrity who was dragged into modern tech. He sounds like the kid who would have loved being dropped into a maker lab. “Ever since I was a teenager, I’ve always been kind of a geek or nerd about technical things,” Osmond said.

That curiosity still drives him today. He studies the tools behind his stage production and experiments with new ways to keep the show fresh. In many ways, technology has become another creative instrument.

Donny Osmond’s favorite app might surprise you

When I asked Donny which apps he uses the most, the answer revealed a different side of the performer. “I’d have to say, uh, Google Sheets because, uh, I’ve created algorithms,” Osmond said.

He enjoys building detailed spreadsheets and analyzing data. His phone of choice is a foldable device that allows him to view larger spreadsheets easily. Osmond also embraces connected security technology. He said he uses cameras and smart alarm systems to monitor his homes, dressing room and other properties so he always knows what is happening around him.

For someone known around the world as a singer and performer, it is an unexpectedly technical hobby.

Donny Osmond sees both the promise and risks of AI

Artificial intelligence has sparked debate across music, film and media. Some artists worry about misuse or losing control of their voice and likeness. Osmond takes a balanced view. “Any technology put in the wrong hands can turn into nefarious things, but look at the good it can do,” Osmond said.

From medicine to entertainment, he believes AI has the potential to drive major advances. “What a great time to be alive with today’s technology. It’s amazing to watch it all happen in real time,” Osmond said. At the same time, he believes society must stay engaged with technological progress rather than fear it. “If we run away from technology, other countries and other people are going to be way ahead of us,” Osmond said.

Speaking of technology, Osmond says his music may already have made it into space. During our conversation, he said one of his songs was reportedly used to test the sound system on a spacecraft capsule. “They actually used my song ‘Start Again’ from my latest album to test the sound system on one of the capsules,” Osmond said.

He then mentioned another story he has heard many times over the years. “When they went to the moon in the Apollo missions, and we did go to the moon, by the way, they took a tape of music with them. And on that music is Andy Williams singing ‘Aquarius.’ I’m singing background vocals on that song. They left the tape on the moon. My voice is sitting on the moon.”

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Social media would have changed the early Donny Osmond years

Osmond also reflected on how today’s digital platforms might have changed his early career. “Can you imagine what I could have done during the ‘Puppy Love’ years with social media?” Osmond said.

At the height of his teen idol fame, fans lined up outside television studios and concerts hoping to catch a glimpse of him. Today, that kind of connection often happens through social platforms and digital communities. It is one more example of how technology has reshaped the entertainment industry.

A career that continues to evolve

Donny Osmond first rose to fame performing with his brothers as part of the Osmonds. The family group became a television sensation in the late 1960s and early 1970s with appearances on shows like “The Andy Williams Show.” Soon after, his sister Marie stepped into the spotlight, and the two became household names with their hit variety series “Donny & Marie.” Decades later, the siblings reunited for a highly successful Las Vegas residency that ran for more than a decade.

Over the years, Osmond has released dozens of albums, starred in television shows, performed on Broadway and built a long-running Las Vegas career. Today, he headlines his own residency at Harrah’s Las Vegas, where he performs several nights a week. The show has been extended through May 2026, a testament to its continued popularity with audiences. Many younger fans now discover Osmond through social media clips, streaming platforms and live performances in Las Vegas.

Technology now plays a role in how he connects with fans as well. Osmond keeps fans connected through the Donny app (donnyosmondapp.com), which brings together news, videos, tour updates and a timeline of his career in one place. Fans can also find tickets, show information and updates at Donny.com, the official website he referenced during our interview. By blending nostalgia with modern technology, Osmond continues to reach fans across generations while pushing his show into new territory.

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Kurt’s key takeaways

Donny Osmond’s career is proof that curiosity can keep an artist moving forward. Instead of resisting change, he continues exploring the technology that’s shaping our world today. From AI stage performances to data-driven apps and smart home systems, Osmond approaches technology with the same enthusiasm he brings to performing. Be sure to listen to or watch the “Beyond Connected” conversation with Donny Osmond to hear more about how he blends entertainment and technology.

If you could use AI to meet a younger version of yourself, what would you ask them? Let us know by writing to us at Cyberguy.com.

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