20 Rare Photos Of Celebs As Awkward Teens

Some people are cheerleaders or athletes in high school and say that it was the greatest time, but many others admit that being a teenager meant experiencing some tough moments. When we have our own kids and they become teens, we might be fairly nervous about how they'll fare during high school. Piles of homework, social situations, and hopes for the future are all things that we will help our children navigate. (And hopefully, we can stop ourselves from sharing too many embarrassing stories from our high school years.)

When we think about celebrities, we might not assume that they felt awkward (or looked awkward) during their teenage years. The stars who we watch on TV or in movies or who create the hit songs that we love listening to seem so beautiful and confident. The truth is that many of them have said that they had a less-than-perfect time in high school and that they were pretty awkward. When stars talk about that in interviews, we can relate to them, even if we're a bit amazed that we have this in common.

There are many high school pictures of celebrities, and they might be surprising to us. Here are 20 rare photos of celebs as awkward teens.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

20 Before Taylor Swift Was The Super Famous 'Shake It Off' Singer, She Had Awkward Braids

via Deveoh and Daily Candid News

On the left, we see an awkward pic of Taylor Swift when she was much younger, and on the right, we see a more recent picture of the singer who has become so famous over the past few years.

These braids totally remind us of some not so great hairstyles that we once had. Maybe we convinced our mom to let us get a certain haircut that wasn't flattering or we wore our hair in side ponytails that we wouldn't today.

It's comforting to know that even a singer-songwriter like Taylor Swift who has very chic hair today once had more awkward locks.

19 Even The Biebs Had A Bad Hair Day Sometimes (This Was Back In Grade 8)

via Pinterest and Vanity Fair

We can't help but jam to Justin Bieber's tunes like "Sorry" and "What Do You Mean?" even if some of his news stories are a bit unflattering. We would also have to admit that these days, his hair looks pretty good. Whether he's got hair that is almost down to his shoulders or it's a bit shorter, he has a lot of style.

Back in grade eight, his hair was a bit more awkward than that, and we can see the evidence. The picture on the left is his eighth-grade yearbook photo.

Scooter Braun, Justin's now manager, found him on YouTube in 2008 when he was only 12 or 13, according to Forbes. This photo must have been taken right before then or around the same time.

18 'Complicated' Singer Avril Lavigne Has Come A Long Way Since Her Awkward School Pic

via Pinterest and Evening Standard

In 2002, Avril Lavigne's song "Complicated" was one of those inescapable pop hits that played on every radio station and in every store. Anyone who was in their pre-teens or teens around that time was probably a big fan.

It's interesting to see this picture of Avril before she was famous: on the left, we can see the awkward school pic with her round bob hairstyle and sweet smile.

When Avril became famous, she was known for her "skater girl" kind of style and wore a lot of baggy clothes (and we can't forget the ties that she loved). The 34-year-old is looking much more sophisticated these days.

17 'Malibu' Singer Miley Cyrus Went From Messy Hair And A Cheesy Grin To Her Flawless 2019 Look

via Teen Vogue and KiSS 92.5

There aren't a ton of child stars who are still well-known, but Miley Cyrus has fared well. She has had recent hit songs like "Malibu" and recently married her true love Liam Hemsworth. Her mid-2000s show Hannah Montana made her really famous, and she has put out many albums.

In the photo on the left, we realize that like the others on this list, Miley Cyrus was an awkward teen. She had really messy hair, which is a stark contrast to the photo on the right which was snapped in 2010. These days, Miley has really silky and smooth hair, and she definitely looks more grown up.

16 Before Becoming A Beautiful Mama Of Two, Blake Lively Had A Goofy Grin

via Pinterest and ONTD - LiveJournal

Blake Lively seems like the kind of girl who would be so popular in high school that girls would want to be her and guys would be asking to carry her textbooks everywhere (if people still do that...). It turns out that even Blake Lively has an awkward teen pic.

She's smiling in this school photo and has a really toothy grin, and it's a big contrast to the photo on the right which is more recent. We're used to seeing Blake in the kinds of clothes that could honestly be on the runway, and everyone is a fan of the mama of two daughters.

Blake didn't have the best time in high school: according to Elite Daily, the star posted on her social media, "Kids used to make fun of me in elementary school by calling me Big Bird (because I was 'too tall' and had 'yellow' hair)."

15 Pop Culture Personality Ryan Seacrest Is Totally Unrecognizable In This Old Picture

via Deveoh and Daily Mail

Ryan Seacrest is known for hosting Live with Kelly and Ryan and New Year's Rockin' Eve. He is also the creator and executive producer of Keeping Up With the Kardashians.

Before the pop culture personality became famous, he also had a pretty awkward school picture. We can see this photo on the left (and the striped shirt is cute, right?). On the right is a more recent picture of Ryan wearing a fashionable combination of a navy sweater, blue scarf, navy pants, and a grey jacket. The sunglasses and coffee and bag totally signal that he's cool and also a celebrity.

14 Actress Rashida Jones Once Had Very Messy Bangs... And Now She's Got The Perfect Ones

via eBaum's World and Daily Mail

When a woman looks good in bangs, she really can't try another look. Well, she can, but the hairstyle becomes a part of her. That seems to be true of actress Rashida Jones since we can see that in her teenage picture on the left, she had wispy bangs, and on the right, she has much sleeker bangs. Her life has changed since she is now a successful actress, but she kept the bangs.

The actress who has starred in movies like Celeste and Jesse Forever and the TV show Angie Tribeca is also a new mom. In September 2018, Us Weekly reported that she had her son, Isaiah, several months before that.

13 We Love Seeing Drake's Adorable (And Awkward) Glasses

via Teen Vogue and Eonline

It's super tough to picture Drake as an awkward teenager since he is so stylish today. The rapper hails from Canada and even starred on the teen drama Degrassi for a little while. Before he was a well-known musician beloved for his lyrics and beats, he did have an awkward teen pic of his own, which we can see on the left. (But, hey, we think that his jean jacket and glasses are so cute.) On the right, we see a more recent picture of the star in a fashionable black suit.

The 32-year-old star grew up in Toronto and started getting noticed for his music in 2006 when he had a mixtape that came out. It's really cool to see how famous and successful he has gotten in the time since.

12 Zooey Deschanel's Beloved Bangs Were Once Wispy And Wild, And Now She's Mama To Charlie And Elsie

via eBaum's World and Hello Magazine

Another celeb who loves bangs, Zooey Deschanel is amazing as Jess on New Girl and we loved watching her in 500 Days Of Summer. She and her husband Jacob Pechenik have two children: one-year-old son Charlie and three-year-old daughter Elsie.

Before she was a mom of two and also a famous actress, Zooey had super wispy bangs, as we can see in this awkward pic of the star as a teenager.

In an interview with Parents magazine, the star said about motherhood, "I've changed completely. You don't realize what a sort of selfish existence you live in until you have kids."

11 Jennifer Lawrence's Journey From Awkward Teen To The Coolest Girl In Hollywood Is Complete

via Teen Vogue and Daily Mail

We would never think that Jennifer Lawrence, who starred in The Hunger Games franchise and many films since, would have an awkward photo from her teenage years. She did, and we can see it on the left. She's wearing the half-up, half-down hairstyle that many teen girls do, along with very innocent-looking earrings and a bright green top.

When Jennifer Lawrence was on the cover of Vanity Fair in 2013, she said in the interview, "I didn’t go to high school. I am vastly uneducated.” It seems like she skipped having a high school experience as she was 14 when she was found by a talent scout.

10 Funny Actress Emma Stone Always Looked Like A Sweetheart, Just With A Big Toothy Grin

via Teen Vogue and Zimbio

If we didn't know that it was Emma Stone in the teen pic on the left, we would totally guess because she looks the same, just younger. It's interesting to see that her hairstyle is very similar in both pictures: on the left, she has a very piecey bob, and on the right, she has a very shiny "lob" or long bob that falls just past her shoulders.

According to Vanity Fair, Emma left high school, and she said, “I did Superbad in what would’ve been my senior year. I was playing a senior, and had I graduated I would’ve missed that opportunity, and had I missed that opportunity I wouldn’t be here right now.”

9 We Would Never Recognize 'Mad Men' Star January Jones And Her Super Fluffy Short Hair

via deveoh and Pinterest

Can we believe that is January Jones on the left?! Probably not. This is definitely a rare picture of the Mad Men actress as an awkward teenager. The short hairstyle, gap in her tooth, and patterned top all complete the look. In the picture on the right, we see January Jones more like we recognize her today: with perfect hair and makeup.

In a 2009 interview with Vanity Fair, the actress talked about that time in her life: she said, "I was always was kind of shy and had a small group of friends and just didn’t take part in… I mean, freshman year I was in tennis and track and some things, but then I just sort of stopped being in anything and just kind of made my way through and graduated early."

8 This Curly-Haired Teenage Liam Hemsworth Turned Into Mr. Miley Cyrus And A Beloved Actor

via InStyle and Teen Vogue

Yup, that's Liam Hemsworth on the left, even if we might not recognize the super curly blonde hair. Fans are more used to seeing the actor looking like he does in the photo on the right, holding hands with his now-wife, singer Miley Cyrus.

He's definitely left those awkward high school days and now is a famous actor. According to Elle, he said about his engagement to Miley, "We've been through so much together over the last 10 years, so [I] felt like it was time."

These stars are proof that awkward high school phases don't last forever, and we love seeing these rare and awkward pics.

7 Fergie Rocked Some Really Curly Hair Before Rocking Being A Mama To Son Axl

via InStyle and Daily Mail

Fergie is now doing the co-parenting thing with Josh Duhamel, and the pair got divorced in 2017. They share a son, Axl, who is now five years old. In an interview with ABC News after having her son, Fergie said, "Now I'm getting more into the flats section because I have a kid. So pregnancy and becoming a mom have really lowered my heels!"

Before Fergie was a mama (and in the famous band The Black Eyed Peas before becoming a solo star), she had really curly hair. It's fun to see this high school picture of the singer. This hairstyle was so popular back then: incredibly curly with bangs. She really rocked it.

6 Even Kendall Jenner Had An Awkward Teen Pic

via Teen Vogue and CelebMafia

Kendall Jenner is a model (and a member of such a famous family, of course), so we wouldn't really expect her to look awkward. Of course, we know that even the most stylish people can still have teen pictures that fall into that category, and it turns out that even Kendall Jenner does, too. She has a cute smile, though.

We get a glimpse of her teen self in this awkward pic on the left. The more recent picture on the right shows us that even a pair of jeans and T-shirt, which would be pretty plain on anyone else, look like fashion success on Kendall.

5 An Awkward Bob To Gorgeous Mom Of Almost Four: Kim Kardashian West's Journey

via InStyle and Daily Mail

We get a glimpse of Kim Kardashian West during her teenage years when see the photo on the left. Her hair was definitely pretty awkward and her bob was flipping up at the bottom, which has happened to everyone who has had this hairstyle at one point or another. The photo on the left shows us her stylish recent self, wearing all pink and with her little ones.

These days, the star is almost a mama to four kids as she is currently expecting her fourth child (through a surrogate). According to People, she said, “I was truthfully thinking about just naming him Rob, after my brother, Rob. But then it’s kind of like North, Saint, Chicago, Rob. It doesn’t really go, but I was really feeling that. And my brother approved it, so that’s like our one kind of name.”

4 Jeremy Renner Went From Mullet To Hollywood Hunk

daveoh & pinterest

It's amazing to see the difference between Jeremy Renner's awkward teen picture and the more recent snapshot of him on the right. Yes, his hair was really... high. And kind of square. It's a confusing hairstyle, but it's also good to know that these things happen to all of us.

Since then, Jeremy Renner has become really well-known as an actor. His main roles include Marvel films such as Thor and The Avengers, along with Tag and Arrival.

The actor is also a dad to daughter Ava, who was born in 2013 and is now six years old, and is co-parenting with his ex-wife Sonni Pacheco.

3 'Twilight' Actor Taylor Lautner Once Had Really Wild Hair (And He's Got It Under Control Now)

via Teen Vogue and Daily Mail

Taylor Lautner is adorable in the Twilight movies as Jacob, and way before that, he was an awkward teen. We all go through that stage, right?! In the picture on the left, he's got really wild hair but he still looks like a sweet, younger version of himself. In the photo on the right, we see a more recent photo, and he's definitely got a more grown-up sense of style. We approve of the scruffy beard and baseball cap.

Taylor was a teenager when he got the part of Jacob so while he has an awkward teen pic, he definitely got the Hollywood experience since he starred in such a famous franchise. The star is now 27.

2 'High School Musical' Star Ashley Tisdale Had Awkward Curls (vs Now With Her Chic Hairstyle)

via Pinterest and HawtCelebs

High School Musical came out in 2006 and one of the stars, Ashley Tisdale, was in her early 20s, so she wasn't very far past high school herself. In a 2018 interview with Teen Vogue, she said, “[High School Musical] is so long ago for me. It’s almost like a past life."

She might say the same thing about her own high school experience. Seeing the awkward pic of her on the left makes us realize that she has definitely grown up a lot since those days, like the rest of the stars on this list. Her hair has even changed from very curly to chic.

1 Gina Rodriguez's Awkward Teenage Photo Is Still So Charming (Just Like The Actress)

via HerMoments.com and HawtCelebs

We love Gina Rodriguez. She's awesome as Jane Villanueva on her long-running CW drama and she's in the new Netflix film Someone Great. Before becoming a famous actress, she also had an awkward teen picture... but she was still really charming. We would use that word to describe her in general.

As the actress told Best Health magazine in 2018, “I’m still hard on myself, but I would definitely love to tell my younger self not to be.” That is good advice for everyone, particularly for teenagers. She is also outspoken about young girls being able to go to school and learn.

Sources: Abcnews.go.com, Instyle.com, Deveoh.com, Teenvogue.com, People.com, Forbes.com, Vanityfair.com, Usmagazine.com, Parents.com, Vanityfair.com, Teenvogue.com, Besthealthmag.ca, Acbnews.go.com, Elle.com, People.com

More in Hilarious