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    Home » News » Going Back In Time To Some Of Your Favorite Country Artists’ High School Photos

    Going Back In Time To Some Of Your Favorite Country Artists’ High School Photos

    Easton RexBy Easton RexOctober 12, 2023 News
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    George Strait Dolly Parton Blake Shelton
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    High school was the worst.

    A.I. has been all the rage lately, and the latest trend featuring the new tech is A.I. generated 90’s high school yearbook photos. On that topic, why not take a trip down memory lane and take a look back at what some of our favorite country artists actually looked like back in high school. Hopefully it’ll help us not feel so insecure about our own cringy yearbook pics.

    Chris Stapleton

    He’s barely even recognizable! Obviously you wouldn’t expect Chris to have his iconic long hair and beard way back then, but he looks like a completely different person with a clean shave and a neat haircut. If you knew Chris back in high school and ran into him today, I doubt you’d be able to recognize him.

    Dolly Parton

    It has been documented multiple times that Dolly was a natural beauty in her younger days, and it’s clear that was true from the start. She established her iconic look early, with that big hairstyle sticking with her to this day. It’s safe to say Dolly was probably getting plenty of attention from the boys in school.

    Keith Urban

    Look, we’ve all had questionable haircuts in our lives. Lord knows I have. And in Keith’s defense, it was the 80s, so this probably wasn’t even the worst at his school. But the highlighted spikes with the mullet is not a look anyone could pull off. Maybe they did things different in Australia back then, but here in America it’s a good thing he grew out of this look.

    Kenny Chesney

    I’ll be damned, he does own shirts with sleeves. At least, he used to. Looking at this well dressed young man you would never know that Kenny would make his name in music as the straw hat, cutoff wearing, beach loving uncle of country music. He sure did get started on that tan early, though.

    Shania Twain

    There’s no doubt Shania was breaking hearts from day one. She has that exact look of the “it” girl we all know in school, the one who was the prettiest girl and knew it. I don’t know what occasion had her breaking out this outfit, but there’s no doubt she was the talk of the town at whatever the event was.

    Blake Shelton

    Woah. You could’ve given me 100 guesses and I never could have told you that this awkward, dorky looking kid would turn into one of the biggest stars of the 2000s. The iconic mullet is there, but beyond that there isn’t much here that’s recognizable as Blake. When you hear the kids talk about a “Glow Up”, this is what they mean.

    George Strait

    It is entirely possible this is the last time anyone saw George Strait without a cowboy hat on. I’m kidding of course, but it is a bit jarring seeing the king of country music in a suit and tie instead of his usual hat and pearl snap. Even back then George had his trademark smile that has lasted him through over 40 years of hit making.

    Johnny Cash

    For some of us it was a tough call whether or not to smile in our school picture. Not for Johnny. The man in black was never a particularly smiley person during his career, so it’s oddly comforting to know that was true even in his youth. You can even see the beginnings of his iconic slicked back hair style, albeit a shorter version.

    Parker McCollum

    I don’t have any idea if Parker was a good football player or not, but being a good looking young man on the football team that can also sing the way he can must’ve been a real hit with the ladies. Your first reaction might be to question the haircut, but remember that this was the late 2000s. The Bieber “swoop” was all the rage at that time, so it’s understandable. That doesn’t make it a good look, though.

    Morgan Wallen

    What a baller. Wallen has talked about his baseball career before and his stats actually weren’t too bad (he lead his team in home runs). His iconic mullet might not have come until later on, but he has that classic “I’m cool and I know it” swag every baseball kid in your high school seemed to have. What is it with singers being great athletes too?

    Cleto Cordero (Flatland Cavalry)

    You might know him better as the lead singer of Flatland Cavalry, but even if you did know his name, you probably didn’t recognize him without his now iconic mustache. High school boys have some strange infatuation with having their shirts off as much as possible, and it’s good to know one of our favorite frontmen was no exception.

    Blake shelton chris stapleton Dolly Parton George Strait Keith urban Kenny Chesney Shania Twain
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    July 29, 2025

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