Why Did Donny Osmond Spend Christmas in Jail!?! (Exclusive)

Donny Osmond with jail bars collage
Everett Collection

Donny Osmond’s been in headlines since he was a teen, so he knows that when he mentions that he once spent Christmas in jail, he’s going to turn heads. “Wait, what? How did we not know that?” we ask. The always-upbeat and playful showman wasn’t kidding when he casually mentioned this experience during an interview we had with him over the summer.

Osmond, who’s currently finishing a four-week run in Scotland, was excited to return to the stage to do Joseph and the Amazing Technicolor Dreamcoat, this time playing the Pharaoh. The famed vocalist is responsible for catapulting the musical to mainstream popularity, having logged thousands of performances between 1992 and 1997, and then reprising his role for a 1999 film.

“When Andrew Lloyd Webber calls and says, ‘Are you willing to do this?’ You don’t turn it down,” he had shared about the current show, which goes through Dec. 29 .“Plus, I’m going to have so much fun doing that thing. It’s going to be so hilarious.” Having done the show for six years, he was more than excited to take on a different role before he returns to Harrah’s in Las Vegas for next year’s residency.

 

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But let’s get back to Osmond spending Christmas in jail. We asked what the holidays were like for Osmond, having grown up as one of nine kids, and if he remembered something special he received or what that chaos might have been like. His response:

“I could tell you my worst Christmas,” he pauses. “I was about 10 or 11 years old, maybe even 12, and I spent the day in jail.”

What could the adorable, sweet-sounding young Donny, who hails from a Mormon family, have possibly done to spend Christmas in jail?

“I was in jail all day on Christmas Day. It was the worst Christmas of my life,” he explains. “I was in Japan with my brothers, and we were doing this comedy television show that they were taping on Christmas Day, and we played to all these people in jail, this family, these brothers that were in jail. I was wearing one of those striped outfits, but it was a comedy skit, and it took all day long. So, I spent Christmas Day behind bars.”

THE JERRY LEWIS SHOW -- Episode 17 -- Aired 01/30/1968 -- Pictured: The Osmonds (l-r) Wayne Osmond, Alan Osmond, Merrill Osmond, Donny Osmond, Jay Osmond, singing "Then I'll Be Happy" --

Frank Carroll/NBCU Photo Bank

Yeah, we fell for it, too. The icon has never come close to spending real time behind bars. He was joking a bit telling the story — but it was indeed his worst Christmas.

Thankfully, the superstar has plenty of fond memories of the holidays growing up, too. “We had wonderful Christmases. Most of those times were obviously creating Christmas shows, whether it be a family Christmas show or The Donny & Marie Christmas Show. They don’t make those kinds of shows anymore, unfortunately, where it’s just warm and fuzzy. It’s not in vogue for some reason anymore. It’s so plastic and so produced. Whereas back then it was a little bit more authentic.”

Well, authentic is what Osmond is all about. He’ll return to Harrah’s next year and continue to pack the house delivering his authentic brand of Americana.

 

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