How Donny Osmond Rose to the Top After Admitting He ‘Once Lost It All’: ‘Starting All Over Again’

Sometimes when Donny Osmond watches his grandchildren play, he’s struck by how different his life was when he was young. “I see my little grandkids and I’m thinking, ‘I worked with Bob Hope when I was that age’ — and it’s, like, whoa,” he exclusively tells Closer.

Donny admits his childhood “was nothing but work — dancing in front of mirrors and sitting at the piano learning my parts with five-part harmonies.” But he credits those early lessons and the discipline he developed for his ability to persevere through six decades in the entertainment industry. And he’s not done yet. In 2023, his live show at Harrah’s Las Vegas, Donny Osmond: The Las Vegas Residency, won Best Headliner and several other accolades.

“It probably means more to me now because I once lost it all,” he confides. Though he’s only 66, Donny is every inch a showbiz veteran — and he has the stories and scars to prove it. At 5, he began performing with his older brothers’ barbershop quartet, the Osmond Brothers, who were regulars on The Andy Williams Show from 1962 to 1967.

Donny admits that he and his siblings grew up isolated from other kids. “My friends were adults and legends,” he remembers. Some of his favorite showbiz memories are of learning at the knees of some of entertainment’s most iconic personalities.

“I always kind of looked at Andy Williams as a father figure,” Donny says. “He taught me how to breathe while singing. He gave me lessons on how to do it right.” Those years provided a master class. “Being around Elvis Presley and watching how he controls an audience was influential,” he says. “You can’t go to a university and learn comedy from Jerry Lewis or Milton Berle or Bob Hope — but those were all people I worked with from a young age.”

Donny Osmond’s Sibling Rivalry

As a youngster, Donny forged a special relationship with his sister, Marie, that would shape the trajectory of both their lives. “Marie and I were best friends from the get-go,” he says. “When my brothers were performing and traveling, it was Donny and Marie back home playing in the backyard together.”

That special connection proved irresistible to TV audiences who made Donny & Marie, which aired from 1976 to 1979, a huge hit. “We were the youngest co-hosts of a television show in history,” he notes. “That rapport we had as little kids went right into it. It was natural. It wasn’t scripted, it was real.”

Of course, by the time Donny & Marie debuted, Donny was already a pro. “When I was 12, I started recording ‘One Bad Apple’ and music started making sense to me,” he remembers. “Up until that time, I was basically performing by rote. But at 12, the creative juices kicked in.”

Not long after “One Bad Apple” hit No. 1, the Osmonds began recording songs with Donny singing lead. Tunes like “Go Away Little Girl” and “Puppy Love” made him a teen heartthrob — which was a double-edged sword. “My image was teenybopper, so the girls loved me, but the guys hated me,” he says.

The worst experience was the day Rolling Stone magazine snarkily took aim at teenage Donny. “I was 15 or 16, and they came out with an article that said, ‘The worst day in rock ’n’ roll history was the day Donny Osmond was born,’” he recalls, wincing at the memory. Despite his popularity, Donny often felt sidelined and disrespected by the media. “Once, we played an arena in Nashville,” he says. “The screaming, the decibels of that concert were unbelievable. But the next day in the newspaper, they ripped me apart.”

TV’s Donny & Marie brought the performer to another level of fame — and also presented a bridge to the past. Many of the performers Donny had worked with as a child, like Bob Hope, Milton Berle and Bing Crosby, were guests. He recalls the time Lucille Ball appeared in a comedy sketch and took over.

“She changed the lighting, the script, the direction — but she did it in a way that was so professional and without being bossy,” Donny recalls. “We all listened to her, and it turned out great.”

In 1979, Donny & Marie won the People’s Choice Award for Favorite TV Variety Program, but the stress of a weekly series wore on its young stars. “We were doing at least an album’s worth of music every week,” he says. “We were learning comedy skits, the concert segments, the choreography. It was just nonstop. And when we weren’t doing the Donny & Marie show, we were on tour! It was like a continuation of my childhood.”

After the intensity of his early career, Donny deserved a private life. He wed Debbie Glenn, his secret sweetheart of three years, in 1978, and their first son, Don Jr., was born the following year.

As the 1980s dawned, new challenges and obstacles were thrown in Donny’s path. Like so many people who attain success young, he had a difficult time finding acceptance as an adult performer. “Throughout the ’80s, I was pretty much in obscurity,” Donny says. “There was a time in 1988 when I was forced to think about changing jobs because nothing was working. I couldn’t get a record deal. My career had come to a complete stop.”

The difficulties didn’t end there. By the late 1970s, the Osmond family was reportedly worth $70 million to $100 million, but outside business partners, who promised to diversify their finances, made poor choices and squandered millions. By 1983, the family was broke.

“I had lost all my money,” recalls Donny. “And I had a family to support.” Despite his sizable talent and longtime name recognition, Donny start- ed submitting demos to people who could help his career. “I had to swallow my pride and realize that I was starting all over again,” he says. “It hurt.”

Initially only released in the U.K., Donny’s 1988 single “Soldier of Love” started receiving airplay on a New York radio station, leading to the start of his career comeback. “The decade of the ’80s was the worst and best decade of my life,” says Donny. “Because I lost everything … and then realized how much [my career] meant to me when I got it back.”

Donny Osmond Is His Own Man

After spending 11 years on the Las Vegas Strip performing with Marie, Donny launched a new show in 2021 that’s a celebration of his longevity as a performer. “I do a 90-minute show, and it covers 60 years of show business. Everything I’ve done,” says Donny, who even has a segment where the audience chooses the song. He and his band will perform any tune Donny has ever recorded. “Many different generations know me for different things,” he says. “We put it all together in this show.”

The star returns to Harrah’s Las Vegas in late August and his residency is scheduled to run through the rest of the year. As much as Donny is enjoying this chapter of his life, he can envision a quieter future.

“I see the light at the end of the tunnel,” he admits. “As soon as I can’t give it the energy that I give it every night, I will close the curtain. I don’t see that happening right away, but all good things come to an end.”