Little Ladd
"This 1970-something school pic of my husband always makes me smile," Ree says. "And sometimes cry, depending on what my hormones are up to."
"Cranky Pioneer Woman"
Here's Ree practicing ballet in 1986. Can you tell dance was her passion?! 😂
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Paige Got Her Wings
"A photographer's assistant was sitting under the table holding on to Paige's roly poly legs and I was standing next to the photographer trying to get her to look at the camera," Ree says. "But her cheeks were so chubby, she couldn't hold her head up!"
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Doing Double Duty
Todd really didn't want to be put down that day. Here's proof that cowboys really only need one arm to work with!
First Day of School
"This was not a costume," Ree admits. "I REPEAT: THIS WAS NOT A COSTUME. I was on my way to the bus."
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B-Man in 2006
Here's Bryce before he turned into an Anthony Michael Hall lookalike.
Tinier Times
"My tiny girls (and my tiny arms, ha) in Yellowstone in...2003? Or maybe it was 1947," Ree says. "Either way, it was forever ago."
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Ladd in 1970-Something
"He was the youngest of three boys and I've heard reports that he was ornery," Ree says. "I believe the reports."
That's a Wrap
"We were so proud of this costume, my oldest and me," Ree recalls. "And then...the dreaded words...they were more terrifying than any Halloween ghoul: 'I hafta go to the bathroom.'" 💀
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Cowboy in Training
It's hard to believe there was a time when Todd was the smallest one in the Drummond family. He's 6'3" now!
Snowball Dance
Thirty five years ago, Ree attended the "Snowball Dance" with her girlfriends. Yes, that's 3-5. No further questions at this time. 😂
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Mama's Girl
Paige's legs have stretched out a bit over the years—but to Ree, her face looks exactly the same!
Braces and Bangs
Wasn't it a rule that everyone had braces at age 13? At this point, Ree was about a year away from falling deeply in love with Billy Idol.
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The Drummond Boys
Bryce and Todd have grown just a few inches since this photo was taken.
Ballet Headshot, 1986
"I can still do the splits!" Ree says. "Okay, no I can't."
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Another Angel
Apparently, Ree loved to dress her daughters as angels. This one was taken at a mall kiosk!
A Couple of Cowboys
These were the days when Ladd had to carry the kids around in the pens as he worked cattle.
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Lifelong Friends
Another angel! To be fair, this was for a performance of The Nutcracker. Fun fact: Ree is still friends with the other girls in this photo, Becky and Michele. ❤️
Marlboro Man
Ladd's looks definitely measure up to his nickname in this throwback!

Kelly O’Sullivan is the senior editor for The Pioneer Woman and manages the website’s social channels, in addition to overseeing content strategy and news.
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