Introduction:
Out of all the incredible things Donny Osmond has achieved in his life, the “Crazy Horses” crooner is most proud of his five sons and 13 grandkids. In addition to juggling his hectic Hollywood schedule, Donny always makes sure to dedicate time to his beautiful family.
The Joseph and the Amazing Technicolor Dreamcoat alum is the doting dad of his boys — Don Jr., Jeremy, Brandon, Christopher and Joshua — with wife Debbie Osmond. The couple’s kids are all grown up and have started families of their own, making Donny and his spouse the loving grandparents of more than a dozen grandchildren.
His eldest, Don Jr., shares four children with his wife, Jessica, while Jeremy is a dad of three with spouse Melisa. Brandon, on the other hand, welcomed his four sons with wife Shelby, and Christopher is a father of one with his love, Alta. At the time Joshua and his wife, Summer, wed in June 2020, they exclusively told Closer they “definitely want to have kids,” but they planned to wait “a couple of years.” The pair welcomed their first child together, son Beckham, in September 2022.
Considering Donny loves nothing more than being with his huge brood, he makes sure to take advantage of his time off. When Donny concluded his 11-year Las Vegas residency with sister Marie Osmond in November 2019, he couldn’t wait to reunite with his adorable grandchildren.
The former Dancing With the Stars contestant did just that when he celebrated his birthday a month after his final bow in Las Vegas. “It’s been a wonderful birthday — one I’ll never forget,” the Masked Singer alum captioned a photo of his entire family via Instagram in December 2019. “My favorite birthday gift this year is a holiday season off from performing so that I can spend time with my dear wife and family. I haven’t had that opportunity since 2010.”
Since Donny hasn’t had the luxury of scheduling work around family functions for nearly a decade, the “I’ll Make a Man out of You” singer said he was looking forward to making up on lost time. “I almost forgot how nice it is to [have] my loved ones around me,” he gushed. “It’s given me time to reflect on how important family and friends really are.”
Throughout his iconic career, Donny has done an incredible job juggling his work while continuing to be a dedicated father and grandfather. However, the former teen idol actually credits his wife of over 40 years for being the best family matriarch a husband could ask for.
“I am particularly grateful that my dear Debbie has been able to be home with our children and has been such a powerful and uplifting influence on each one of our family,” he revealed to Third Hour in 2014. “Especially in her great support of me in my crazy career that takes me away from the home so much.”
Scroll through the gallery below to see Donny’s sweetest pics of his beloved family!
October 2022
“Picking apples with my grandkids in the fall. It doesn’t get better than this,” Donny captioned a sweet video with some of his grandkids.
August 2021
While celebrating the opening night of his solo Las Vegas residency in August 2021, Donny shared a photo of his massive family, including wife Debbie, their sons, grandchildren and daughter-in-laws. “Thank you to everyone that came to opening night yesterday. It made it so special that my family was there and what an opening it was!” he gushed via Instagram.
June 2020
The “Puppy Love” singer proved he had a fun-filled weekend with wife Debbie and their family as they attended grandson Ryder’s flag football game in June 2020. “The perfect way to spend a Saturday —watching our sweet, little Ryder play #FlagFootball,” he captioned the adorable portrait.
February 2020
“We are lucky to call this bright young lady a part of our family,” Donny wrote alongside a selfie of son Brandon and his wife, Shelby, as he wished his daughter-in-law a happy birthday. “She has a huge heart filled with so much love. #happybirthday to our daughter-in-law Shelby! Enjoy this special day.”
February 2020
Donny shared the amazing news that his son Josh was engaged to be married! “Our youngest son, Josh, and his darling girlfriend, Summer, got engaged last night!” the doting dad captioned the photo.
“We are beyond thrilled that Summer will be joining our family! It was a picture-perfect Valentine‘s Day, and an incredible kickoff to Josh‘s birthday weekend,” Donny continued. “Happy birthday and congratulations, Josh! Mom and I are so happy for you. More pictures to come after the wedding. I’ll let them announce that one.”
January 2020
Donny shared the cutest throwback photo with son Brandon in honor of his 35th birthday. “Wishing my son Brandon a very #HappyBirthday! I consider myself lucky beyond words to call you my son,” the legendary performer captioned the post. “It’s remarkable how quickly the years have flown by, but watching you learn, grow, and create a family of your own is a precious gift. Your mother and I love you very much.”
November 2019
Donny shared the sweetest photo while spending some time off with his wife and kids. “I flew home after our show Friday night to cheer for my grandson Dylan at his football game. This was their championship game, and guess what… they won!” the proud grandpa wrote in the caption. “Say hello to the Westlake 7th grade high school #FootballChampions. Congratulations to my wonderful and cool #grandson Dylan. Bapa loves you.”
July 2019
Donny shared a photo while enjoying the summer weather with his little bundles of joy. “My grandkids just pushed me in the pool, so we celebrated by breaking out some #popsicles,” he wrote at the time. “Thanks @popsicle for sending the Osmond family the perfect treat for a hot summer’s day in the pool.”
July 2019
“I’ve just spent four wonderful days with my sons in Gustavus, Alaska,” the Life Is Just What You Make It author wrote in the caption of a photo with his kids. “It’s absolutely beautiful up here! Thanks to Greg Taylor for showing us a great time. We caught our limits of halibut each day. We had a blast, and I’m pretty sure I still smell like fish.”
July 2019
Donny kicked off his boys-only fishing trip with a super cute selfie with his sons. “On my way to #Alaska with my boys. The halibut and salmon are calling for us!” he wrote.
June 2019
What a view! Donny shared a stunning photo in honor of his son Jeremy’s birthday.
April 2019
The “Down by the Lazy River” singer shared the most heartwarming snapshot while relaxing with two of his grandkiddos.
December 2018
Donny’s clan gathered to welcome Josh home from a mission trip.
December 2018
Donny shared a photo from a fun night out with his boys! “A perfect way to wrap up the year… a @utahjazz basketball game with my boys!” he gushed.
December 2018
Fun grandpa! “I took my little grandson Benson to the aquarium today for his birthday,” Donny dished. “He loved the sharks, but I think it was the butterfly on Grandpa’s nose that made him happy.”