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LOL!See All the Times Donny Osmond Made Us Cringe — Out of Love — With His Hilarious Dad Jokes

Entertainment

Jul 24, 2020 3:34 pm·

By Kelly Braun

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We thought Donny Osmond was just an actor, entertainer and singer — but it seems like he’s a comedian as well! The beloved Donny & Marie star has been making fans weak at their knees ever since he first became a teenage heartthrob.

Nowadays, the “I’ll Make a Man Out of You” singer has been keeping his Instagram followers cracking up at his slightly awkward — but totally hilarious — dad jokes! In fact, Donny’s profile is easily one of social media’s most underrated considering we can count on him for a never-ending spree of hilarious posts, comical photos, wacky videos and those LOL-worthy captions too.

To see how truly hilarious he is, scroll through the gallery below to check out some of Donny’s best one-liners that made us cringe out of love!

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July 22, 2020

Donny knows how to keep us laughing! On July 22, he shared a throwback pic of his family on Instagram and in the caption, he hilariously theorized what each one of his siblings may have been thinking at the time.

“Marie: Hey brother, what do you say you and I start our own duo together? We can call it ‘The Marie and Donny Show.’ (That’s probably why my back was turned,” the A-lister wrote with two laughing emojis. “Wayne: If you guys only knew how many hilarious jokes I’ll be telling on stage for the rest of my life.” We can’t get enough of this guy!

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Anyone else? 😂 ⚠️WARNING⚠️: Song may cause spontaneous singing, dancing and jump kicks. 🎥: Jeffrey Clay, I like your choice in workout music. I must admit, I love listening to this one while exercising. 😬

A post shared by Donny Osmond (@donnyosmond) on Jul 14, 2020 at 10:22am PDT

July 14, 2020

Donny reposted a hilarious video of TikTok star Jeffrey Clay working out to his hit song “I’ll Make a Man Out of You” on July 14. “WARNING: Song may cause spontaneous singing, dancing and jump kicks,” he jokingly captioned the clip. “Jeffrey Clay, I like your choice in workout music. I must admit, I love listening to this one while exercising.”

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I recently asked Jerry Anderson, a good friend of mine whom I've known for years, if I could borrow his bobcat to do some work in my backyard. His bobcat was practically brand new (see first picture) and one of his prized possessions. I promised that I'd take good care of it. ⁣ ⁣Well, as luck would have it, it had just rained when I started working, so there was mud everywhere. I figured I could put dry dirt on top of the mud and gravel under the tracks to continue working, but the bobcat just kept sinking lower and lower. It was so full of mud, I could barely get out of it! I called Jerry up and told him, "I think you better come over." ⁣ ⁣He had to take a break in his #construction project, and brought his team over to save the bobcat. That's when we took this second picture. I felt terrible for covering his pristinely new #bobcat in mud, so I promised him I would clean it up. I hired a luxury car detailer to come and clean every inch of the bobcat. He did such a fantastic job, you could eat off of it! He even put air fresheners in there. ⁣ ⁣ At 4am the next day, I drove the newly-cleaned bobcat over to Jerry's house and left it in his driveway with balloons tied to it saying "I'm sorry". 😆⁣ ⁣ I hear my mishap has since become the running joke of the contractors in Utah. Donny Osmond buried a bobcat! Whoops.😬 I guess I better stay in show business and leave construction to the professionals.

A post shared by Donny Osmond (@donnyosmond) on Jul 8, 2020 at 1:21pm PDT

July 8, 2020

Donny revealed he got himself into a bit of a mess while borrowing a neighbor’s skid-steer loader in early July. Although the star “promised that [he’d] take good care of” the massive tool, he had a mishap when it rained the night he began his project.

“There was mud everywhere. I figured I could put dry dirt on top of the mud and gravel under the tracks to continue working, but the bobcat just kept sinking lower and lower,” he explained via Instagram alongside a before and after photo of the bobcat in the dirt. “It was so full of mud, I could barely get out of it! I called Jerry up and told him, ‘I think you better come over.'”

Fortunately, Donny’s neighbor “brought his team over” and saved the day. “I felt terrible for covering his pristinely new #bobcat in mud, so I promised him I would clean it up,” Donny continued. “I hired a luxury car detailer to come and clean every inch of the bobcat. He did such a fantastic job, you could eat off of it! He even put air fresheners in there.”

The make matters even funnier, the singer hilariously said he “drove the newly-cleaned bobcat” over to neighbor’s house the next day and “left it in his driveway with balloons tied to it saying ‘I’m sorry.'” After hearing his mistake became the “running joke of the contractors in Utah,” he quipped, “I guess I better stay in show business and leave construction to the professionals.”

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May 14, 2020

Donny shared the most adorable pic of a nurse standing next to his cardboard cutout in a hospital amid the coronavirus pandemic.

“I hear ‘flat Donny’ recently joined this pediatric nurse at work. I’m glad to hear the kids enjoyed his visit!” he gushed alongside the epic photo. “To all of the nurses, doctors and healthcare heroes working on the frontlines, I extend my heartfelt gratitude. Thank you for your hard work, sacrifice and dedication. You are true heroes.

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Donny and Marie Osmond Perform at the Flamingo, Las Vegas, America - 04 Dec 2008

May 13, 2020

Donny reposted a photo a fan shared of their two dogs dressed head to toe in ensembles that he and sister Marie used to wear during their Donny & Marie days.

“On day 44 of quarantine, I discovered what @MarieOsmond and I would look like as dogs,” he captioned the hilarious snap. “Thanks for sharing, @Sweetest_mandms. Anyone else feeling a little bit rock ‘n’ roll today?”

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"What is @maskedsingerfox?" 😆 I can finally say I am a clue on @jeopardy. I'll consider this my greatest accomplishment for this month of quarantine.

A post shared by Donny Osmond (@donnyosmond) on Apr 7, 2020 at 3:01pm PDT

April 7, 2020

When contestants on an episode of Jeopardy! were asked to answer, “Tori Spelling’s unicorn and Donny Osmond’s peacock belted out tunes on this show — that line shouldn’t make any sense, but it’s true,” Donny marveled at the awesome recognition.

“‘What is The Masked Singer?’” the “Go Away Little Girl” singer captioned a snapshot he took of the beloved game show on his TV screen. “I can finally say I am a clue on @Jeopardy. I’ll consider this my greatest accomplishment for this month of quarantine.”

We couldn’t be more grateful for Donny’s epic dad jokes amid the worldwidecoronavirus pandemic!

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March 23, 2020

Donny gave fans an update on how he and sister Marie’s former billboard at the Flamingo Hotel is looking as he shared a photo posted by a fan.

“The Las Vegas Strip may be quiet for a while, but I’m still here watching over the city,” the jokester captioned his Instagram post on March 23. Since closing out their decade-long residency in November 2019, Donny has teased that his ghost “still remains” considering his photo has yet to fade from the building’s refurbished walls.

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A rare sighting of Donny in his natural habitat. 🛠 #FBF

A post shared by Donny Osmond (@donnyosmond) on Feb 21, 2020 at 9:11am PST

February 21, 2020

As Donny shared a photo of himself in his “natural habitat” — a.k.a doing work in the kitchen — he couldn’t help but tease a fan who commented that she thought he was actually cooking.

“Trust me, you don’t want to eat anything I’ve cooked,” he hilariously replied in the comments section of his post. LOL!

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February 20, 2020

Donny is one funny guy! He shared this hilarious photo of a doormat to Instagram and penned the caption, “Every time I see this welcome mat, I have more questions.😂 #ThursdayThoughts.”

Honestly, the best part about this pic is that he’s mentioned after pizza and eBay. Luckily, he doesn’t seem to mind!

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January 31, 2020

While gearing up for the 2020 Super Bowl on February 2, Donny revealed he will be cheering on the Chiefs. Before dishing his bets on the upcoming event, the comedic hunk explained why he’s rooting for the Kansas City team as opposed to the San Francisco 49ers.

“@49ers or @chiefs? I’ve been facing an interesting predicament leading up to this year’s #SuperBowl, but I’ve finally made up my mind…⁣” he wrote on Instagram on January 31. “I’m a big #49ers fan and have been ever since they asked me to sing the National Anthem at what used to be Candlestick Park. ”

However, Donny also revealed the head coach of the Chiefs, Andy Reid, and his wife, Tammy Reid, “are good friends” of his. “I’ve been chatting with Andy over text and wishing him well in the big game,” he added.

After explaining to his fans why he felt torn, Donny finally had a verdict. “Even if Andy and Tammy weren’t reason enough to sway my allegiance (which they are), my taste buds really sealed the deal,” he hilariously confessed. “Kansas City holds a special place in my heart for its world-class B-B-Q. I had the best I’ve ever tasted at a restaurant called Q39. Oh my goodness… you have to try their burnt end appetizer!” LOL!

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January 14, 2020

Donny shared one hilarious response during an Instagram Q&A with fans on January 14. When one of his followers asked what’s on Donny’s “vision board for 2020,” the comedic crooner joked, “What I’m going to do in 2020 I’ve been working on since 2012.” HA! We adore him.

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December 9, 2019

In honor of his birthday, Donny couldn’t help but joke about his age! On Monday, December 9, the “Crazy Horses” crooner shared a sentimental thank you to all his fans, family and friends for making his 62nd birthday so special.

“Thank you for all of the birthday wishes you’ve sent my way today,” he wrote alongside a rare photo of his entire family, including his big brood of kids and grandkids. However, Donny didn’t want to admit he turned the big 6-2 as he joked about celebrating his 29th birthday in the caption.

“As I turn 29 (again 😏), I’m grateful for those of you who have been following my career since the beginning, as well as those of you who are just now discovering who I am,” he adorably quipped. Throughout the rest of the message, the proud family man gushed over spending time with his five sons and lost list of grandchildren.

“I almost forgot how nice it is to wrap up the year with my loved ones around me,” he wrote. “It’s given me time to reflect on how important family and friends really are.”

Donny also offered his sincerest gratitude for those who stuck by his side throughout all the years. “Thank you for all of your kind words and birthday wishes on my social media,” he continued, before concluding, “And yes… I sent myself one of my @amgreetings singing birthday cards. 😂” LOL!

We hope Donny had the best birthday ever!

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DONNY OSMOND AUTOBIOGRAPHY BOOK LAUNCH, WATERSTONES, LONDON, BRITAIN - 06 SEP 2005

November 5, 2019

On November 5, Donny shared photos on social media from a meet and greet with fans at his Las Vegas Residency show just a few days prior. The “Love Me for a Reason” crooner explained that when he was greeted by a longtime fan, he was shocked to see the sweet memento she brought along to show him.

“She asked, ‘Do you recognize this sweater I’m wearing?’ I said, ‘No,'” Donny wrote in the Instagram caption. “She then told me that it was the very same sweater that I wore for the cover of my [2005] autobiography, Life Is Just What You Make It. She took the orange sweater out of her shadowbox to wear to the show that night and showed me printed photos taken the day she bought the sweater for charity.” Aww!

Although Donny was completely taken aback by the fan’s sweet gesture, he couldn’t help but sneak in a hilarious joke at the end of his caption. “I told her I wanted it back. JK,” he adorably teased alongside a winking-eye emoji. LOL!

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It was a wild show last night for #Halloween! 🎃 👻 Our band consisted of The Headless Horseman, Marilyn Monroe, The Blues Brothers, Dracula, Darth Vader and so many more characters. But the scariest costume of all was the person who dressed up like Marie Osmond. Oh wait... that was Marie. 😂😂😂 Marie and I are really going to miss these wonderful people. Only 12 shows remaining. ☹️

A post shared by Donny Osmond (@donnyosmond) on Nov 1, 2019 at 6:09am PDT

October 31, 2019

Donny shared a group pic from him and sister Marie’s Halloween-themed concert for their Las Vegas residency at the Flamingo Hotel and Resort. “It was a wild show last night for Halloween,” the “One Bad Apple” crooner wrote on Instagram following their performance on October 31.

While explaining that some of their backup dancers dressed up as The Headless Horseman, Marilyn Monroe, The Blues Brothers, Dracula, Darth Vader and “so many more characters,” the beloved star joked that his stage partner had the most terrifying costume of them all.

“But the scariest costume of all was the person who dressed up like Marie Osmond,” he hilariously teased. “Oh wait … that was Marie.” LOL!

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Just touched down in London! Long flight, no bag and mistake in my hotel reservation. This is turning out to be a trip I’ll never forget! 🤷🏻‍♂️The good news is I need a shower, and the #London rain is working magic. 😆

A post shared by Donny Osmond (@donnyosmond) on Oct 23, 2019 at 2:47pm PDT

October 23

Donny let his humor get the best of him after a long day of traveling. “Just touched down in London! Long flight, no bag and mistake in my hotel reservation,” the “Close Every Door” crooner wrote alongside a pic of him lying on a park bench on October 23. “This is turning out to be a trip I’ll never forget! The good news is I need a shower, and the #London rain is working magic.” LOL!

We wonder what Donny is up to in England!

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October 14

After surprising his little sister, Marie, on the set of The Talk in honor of her 60th birthday, Donny recalled the time when his brothers performed on the Andy Williams Show with iconic Mary Poppins actress Julie Andrews.

“It was wonderful to see my brothers Alan, Wayne, Merrill and Jay on @thetalk today as we all celebrated Marie’s 60th birthday,” the singer explained in an Instagram post. “I just wish Virl, Tom and Jim could have been there. Next time. 😉 Before I walked out and surprised them, I was hiding in a room so nobody would see me.”

Donny explained that while he was waiting, he “decided to look at some YouTube videos of my bro’s when they first started in the business” and discovered the video of their appearance on the former talk show in 1964.

“I must have been about 4 or 5 years old when they did this,” he continued. “I recall my brothers working tirelessly on their British accents and rehearsing these lines over and over again for their appearance with #JulieAndrews on the #AndyWilliams Show. I laugh every time I hear Merrill try to say ‘indubitably,’ but it was so cute. 😆”

LOL!

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October 2

What a jokester! Donny took to social media on Wednesday, October 2, and shared a throwback pic with some of his brothers. The beloved star teased about their former fashion choices as he joked in the caption about their unique ensembles.

“I hear plaid #blazers are all the rage this season,” the singer hilariously wrote alongside a pic of The Osmonds wearing plaid suits. “As my sons would say, you’re looking at the ‘OGs’ of tartan suits. 😜” LOL!

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September 25

While sharing a review of The Masked Singer season 2 premiere, Donny gave some feedback in the most hilarious way! After the Egg Mask performer was voted off on the first night and unveiled as Johnny Weir, Donny took to Instagram and shared a sweet — and super clever — message for the Olympic figure skater.

The Donny & Marie star adorably joked that although he is no longer on the show, Johnny made a “great egg-xample of how to get out there and work it!⁣” LOL!

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At the #MeetandGreet after the show last night, a woman by the name of Diana Weatherly gave me this 1978 #BerrysWorld comic. I'm sorry if I upset thousands of women in one day, but I have to be honest... I got a great girl! ❤️

A post shared by Donny Osmond (@donnyosmond) on Sep 4, 2019 at 8:35am PDT

September 4

Donny hilariously joked about breaking “thousands” of hearts on the day that he married longtime wife Debbie Osmond in 1978! “At the #MeetandGreet after the show last night, a woman by the name of Diana Weatherly gave me this 1978 #BerrysWorld comic,” the singer explained in the caption on Wednesday, September 4. “I’m sorry if I upset thousands of women in one day, but I have to be honest… I got a great girl! ❤️”

In the post, Donny shared a pic of the comic card that he was talking about. It featured a picture of a little girl crying at a desk. “I know Donny Osmond’s marriage is hard to take, but just remember — Shaun Cassidy is still available!” the illustration’s caption read.

This is too comical!

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Thought I'd lay down on the deck... just for the #halibut.😆🐟 #gonefishing

A post shared by Donny Osmond (@donnyosmond) on Jul 29, 2019 at 7:14am PDT

July 29

Donny shared this pic of him while on a fishing trip to Alaska with all five of his sons! “Thought I’d lay down on the deck … just for the #halibut.😆🐟 #gonefishing.” Look at this massive halibut he caught!

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“We’re bringing saxy back...” 🎶🎷 #TBT #TheOsmonds

A post shared by Donny Osmond (@donnyosmond) on Jun 13, 2019 at 10:06am PDT

June 13

Oh, Donny. The “I’ll Make a Man Out of You” singer shared a super cute throwback with six of his eight siblings.

“We’re bringing saxy back…” 🎶🎷 #TBT #TheOsmonds,” Donny captioned the pic. LOL!

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Googled myself today. Let me clear up a few of your questions: 1. Yes, I'm the singing voice for Captain Li Shang in @Disney's #Mulan. One of my favorite roles yet. 2. Yes. We miss you, #MJ. 3. If I'm ill, I'm just as surprised as you.😆 4. No, I'm not the rabbit (that would be @realjoeyfatone), but I AM the Peacock. 🦚 @maskedsingerfox 5. Yes. It's rather permanent. 6. Nope. Unless you mean "sick" in the way my sons describe something cool, in which case Donny Osmond is pretty sick. 😜 #GoogleYourself

A post shared by Donny Osmond (@donnyosmond) on May 21, 2019 at 12:31pm PDT

May 21

OMG! Donny shared this hysterical screenshot of him Googling himself. He explained all the answers behind the most asked questions in the funniest way in his caption!

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Donny Osmond And Marie Osmond Celebrate 500 Shows At The Flamingo

March 23

Donny shared a series of pics of him holding dogs while singing on stage throughout the years. “I’m really glad the lyrics of one of my biggest hit records featured an animal as cute and cuddly as a puppy. 🐶 Can you imagine the hangups of a song about a skunk? Or a spider? 😳😅 #NationalPuppyDay #PuppyLove.”

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Donny Osmond and Marie Osmond Perform on ABC's "Good Morning America" - August 15, 2008

February 5

“New year, new shoulder … anyone know where I can find a new sister? 😜⁣” Donny captioned a pic he shared of him and sister Marie Osmond. “Kicking off our first show of the year at our home away from home. @flamingovegas, it’s good to be back! Looking forward to seeing you tonight, sis. ⁣#ItTakesTwo #DonnyandMarie #LasVegas.”

What are brothers for if they don’t tease their sisters?!

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Writing music 5 days after shoulder surgery is a little harder than I thought it would be. Maybe I should call this song "Shoulder of Love.“ 😆 Do you have any clever titles for the #NewAlbum? #RecoveryMode #NewMusicAlert

A post shared by Donny Osmond (@donnyosmond) on Jan 9, 2019 at 9:52am PST

January 9

Donny put a funny little twist on his original song title “Soldier of Love” after injuring his shoulder in an accident. “Writing music five days after shoulder surgery is a little harder than I thought it would be,” he wrote. “Maybe I should call this song ‘Shoulder of Love.’ 😆 Do you have any clever titles for the #NewAlbum? #RecoveryMode #NewMusicAlert.” Ha!

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Turns out dancing accidents aren’t so convenient after all.🤷🏻‍♂️ I’m home after a successful shoulder surgery and settling in for some serious #RestandRecovery. My only complaint about the day: my doctor gave me the cold shoulder. 😁

A post shared by Donny Osmond (@donnyosmond) on Jan 4, 2019 at 2:10pm PST

January 4

Even when he’s hurt, Donny always looks on the bright side. “Turns out dancing accidents aren’t so convenient after all,” he hilariously captioned a pic. “I’m home after a successful shoulder surgery and settling in for some serious #RestandRecovery. My only complaint about the day: my doctor gave me the cold shoulder.”

He’s too funny!

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#NewYear... same me. 🤷🏻‍♂️😂 #newyearsresolution

A post shared by Donny Osmond (@donnyosmond) on Jan 2, 2019 at 9:53am PST

January 2

“#NewYear … same me.😂 #newyearsresolution,” the “Puppy Love” singer hilariously captioned a pic he shared of his fake New Year’s resolution — what a comic!

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October 13, 2018

“Happy birthday to my partner in crime, @MarieOsmond! She deserves the very best. And that’s why I work with her. 😉 #DonnyandMarie #ItTakesTwo,” Donny gushed in the caption. LOL!

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Recently found this #throwback ... I think Debbie & I had the same hairdresser. 😂 She looks gorgeous as ever, but the ‘80s clearly got the best of me! #TBT #80sbaby

A post shared by Donny Osmond (@donnyosmond) on Oct 11, 2018 at 1:05pm PDT

October 11, 2018

The proud dad of five shared the cutest throwback with wife Debbie Osmond. “Recently found this #throwback … I think Debbie and I had the same hairdresser,” he wrote in the caption. “She looks gorgeous as ever, but the ‘80s clearly got the best of me! #TBT #80sbaby.” Ha!

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Found our Vegas neighbors backstage at @dancingabc! Didn’t get the blue memo. 🤷🏻‍♂️😜 @bluemangroup #dwts #vegasnight

A post shared by Donny Osmond (@donnyosmond) on Oct 2, 2018 at 3:59pm PDT

October 2, 2018

Donny shared a pic from behind the scenes on Dancing With The Stars. “Found our Vegas neighbors backstage at @dancingabc! Didn’t get the blue memo. 😜@bluemangroup #dwts #vegasnight.” He wasn’t kidding!

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Here's a Thursday #throwback for your enjoyment. You've heard of hairDOs... well this was a notable hairDON'T. 😂😂👽👽 #TBT #DonnyandMarie #GreetingsEarthlings

A post shared by Donny Osmond (@donnyosmond) on Sep 27, 2018 at 11:15am PDT

September 27, 2019

Donny took a stroll down memory lane while checking out some old pics from the TV show Donny & Marie. “Here’s a Thursday #throwback for your enjoyment. You’ve heard of hairDOs … well this was a notable hair DON’T. 😂😂👽👽 #TBT #DonnyandMarie #GreetingsEarthlings,” he hilariously captioned the photo. Look at that ‘fro!

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Back in 2006 @Alfredyankovic called me up and said, "Donny, I wrote this parody on 'Ridin' Dirty' and it's called 'White & Nerdy' and I immediately thought of you." I told him, "Thanks, Al. Appreciate it." This was our unrehearsed first take of the music video. 😂😂 #FBF #WhiteAndNerdy

A post shared by Donny Osmond (@donnyosmond) on Aug 17, 2018 at 11:17am PDT

August 17, 2018

LOL! Donny shared the most hysterical video from back in the day with friend and fellow singer “Weird Al” Yankovic. “Back in 2006 @Alfredyankovic called me up and said, ‘Donny, I wrote this parody on “Ridin’ Dirty” and it’s called “White & Nerdy” and I immediately thought of you,'” Donny explained in the caption. “I told him, ‘Thanks, Al. Appreciate it.’ This was our unrehearsed first take of the music video. 😂😂 #FBF #WhiteAndNerdy.”

We are cracking up at our desks!

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I would wish you a happy #InternationalCatDay, but I'm more of a #PuppyLove kind of guy. I can only imagine what that Donny doll has been through over the years. 😳😂

A post shared by Donny Osmond (@donnyosmond) on Aug 8, 2018 at 3:50pm PDT

August 8, 2018

Poor doll. “I would wish you a happy #InternationalCatDay, but I’m more of a #PuppyLove kind of guy,” the Utah native wrote in the caption. “I can only imagine what that Donny doll has been through over the years. 😳😂”

This is actually so cute!

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Well this was a first! LOL During Marie's segment of the show, lots of beads came off of her dress. It's pretty dangerous to dance when there are beads on the floor like that, so I had to do something before the dancers and I did a big dance number. Little sisters... always making a mess. 🙄😜 #nationaldanceday #dmsummertour #donnyandmarie

A post shared by Donny Osmond (@donnyosmond) on Jul 28, 2018 at 12:18pm PDT

July 28, 2018

Donny took full advantage of embarrassing little sis Marie in a throwback post shared to social media. “Well, this was a first! LOL During Marie’s segment of the show, lots of beads came off of her dress. It’s pretty dangerous to dance when there are beads on the floor like that, so I had to do something before the dancers and I did a big dance number. Little sisters… always making a mess. 🙄😜 #nationaldanceday #dmsummertour #donnyandmarie.”

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