Witherspoon was clearly destined for a career in film! Don’t believe us? Check out this photo of her behind the lens when she was just a toddler.
“Not to brag or anything, but I’m pretty sure I started #FemaleFilmmakerFriday 📹,” Witherspoon joked on Instagram.
In 2017, Witherspoon shared a photo of herself as a toddler (with a bowl cut, no less!) alongside her brother, John. “Happy #nationalsiblingsday to my brother John,” Witherspoon wrote. “Thanks for always laughing at my jokes…and making me laugh….from back in the day till today!”
This throwback of Witherspoon is major “#BackToSchool vibes 🍎.” Witherspoon posted the adorable shot, revealing in its caption that, “Yes, my dress has ‘Reese’ stitched on the front … 😂.”
In August 2020, after Kamala Harris was announced as Joe Biden’s running mate, Witherspoon shared a touching anecdote on Instagram alongside a photo of her as a young girl.
She wrote, “I woke up this morning thinking about a moment from my childhood. In the 3rd grade our teacher asked us what we wanted to be when we grew up, I raised my hand and said, ‘I want to be the first female President of the United States of America.’ Some of the kids laughed, but my teacher looked me in the eye and said, ‘I will be the first person to vote for you, Reese.'”
She continued, “My thoughts today are with women in our country, especially the young Black and Brown girls of our nation. Who have watched their mothers hold up their families, their communities, their cities, their states. Now you know that YOU too can work hard, dedicate your life to service and show up every day to help others, and YOU can RISE to become a Vice Presidential nominee in the United States of America. Today is a truly historic day! #KamalaHarris #WeHaveHerBack”
School Picture Day
Yep, that’s Witherspoon on school picture day with pigtails and a candy necklace around her neck.
“Mom tip: Send your kid to school with a candy necklace so she can share it with all her new friends! 😝,” Witherspoon captioned the adorable shot.
What’s sweeter than Girl Scout Cookies? This photo of young Reese in her uniform! “I bet you can guess who sold the most cookies for Troop 1077. 💯🍪🤗,” the star shared on Instagram.
Go, Reese, Go!
“Say hi to little baby cheerleader Reese,” Witherspoon shared on Instagram alongside a photo of her beaming at the top of the pyramid (where else would a star like her be?) while cheerleading.
What’s that saying? You can take the girl out of the country, but you can’t take the country out of the girl?
Forever a Fashionista
On National Siblings Day in 2019, Witherspoon shared another sweet photo with her brother, John, joking in the caption, “Fashion fades but family is forever?? 😂”
Strike a Pose
Now that’s some headshot! The Legally Blonde star joked that her height, marked as 4’11” on her résumé, is now “a much more impressive 5’2″.”
Witherspoon shared a memory from 1991 when she was just 15 years old, when she attended Deauville Film Festival in France— her first fest!
Red Carpet Ready
Witherspoon rocked up to the 1991 red carpet premiere of The Man in the Moon in cowboy boots, of course!
And she looked impeccably cool at the premiere of the 1993 film, Amongst Friends.
Two ageless wonders, Witherspoon and Paul Rudd (who starred together in Overnight Delivery and How Do You Know) took a selfie together in 1996.
The actress looked like she was having a blast on the red carpet for Romeo + Juliet in 1996.
What’s Up, Bro?
“Aren’t big brothers the best!?” Reese asked on Instagram in honor of her brother’s birthday in October 2016. “#HBD to this guy who has the biggest smile. Thanks for being by my side all these years 💗 I love you! (Fun fact: he also makes the BEST ribs in Nashville! 😋) #BigBrother.”
If you’re going to twin, you might as well do it with your dog! In 2016, Witherspoon shared a photo of her “#twinning” with a pup in matching sweater vests. So chic!
“#TBT to the good ‘ol days 🤓 (aka #CollegeYears),” Witherspoon captioned this photo. Witherspoon attended Stanford, but left after her freshman year to pursue acting.
“There’s a lot to unpack here,” Witherspoon joked of this photo taken at an afterparty in 1996.
She asked Instagram of her very trendy look, “I mean…what is happening with my hair?🤣But most importantly… who else enjoyed this 90’s brown lipstick trend?”
Witherspoon posted this polaroid from the set of the 1998 film Pleasantville.
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