Will Smith, Jennifer Garner, and more stars share retro (sometimes cringeworthy) headshots

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·Editor, Yahoo Entertainment
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  • Jennifer Garner
    Jennifer Garner
    American actress
  • Will Smith
    Will Smith
    American actor
Will Smith, Jennifer Garner, and Tiffany Haddish are some of the celebs sharing their early headshots. (Photos: Getty Images)
Will Smith, Jennifer Garner, and Tiffany Haddish are some of the celebs sharing their early headshots. (Photos: Getty Images)

Before they were stars, Jennifer Garner, Will Smith, Tiffany Haddish, and other recognizable names in Hollywood were just actors looking for their big break. They were armed with big dreams and, of course, the all-important headshot they gave out to get cast in what they hoped was the next critically acclaimed blockbuster.

Over the weekend, as actors reminisced on the early days of their careers with the hashtag #oldheadshotday, some of the faces that turned up looked familiar.

Jennifer Garner

The 13 Going on 30 star is rarely without a smile these days, but that wasn’t so when she first came on the scene.

Why so serious, twenty two year old Jen? #oldheadshotday #1994 #

A post shared by Jennifer Garner (@jennifer.garner) on Apr 27, 2018 at 6:05pm PDT

Will Smith

Smith was the epitome of ’80s cool in so many ways in the photo he shared. Has anyone ever looked fresher?

Yo… The Single Earring was the TRUTH! #oldheadshotday

A post shared by Will Smith (@willsmith) on Apr 28, 2018 at 9:09pm PDT

Katie Holmes

If Holmes used this pic, it’s no wonder she was cast as Joey Potter on Dawson’s Creek.

#oldheadshot #fbf

A post shared by Katie Holmes (@katieholmes212) on Apr 27, 2018 at 7:55pm PDT

Tiffany Haddish

The Girls Trip star managed to keep herself from laughing long enough to snap a few serious photos for her first jobs.


A post shared by Tiffany Haddish (@tiffanyhaddish) on Apr 27, 2018 at 11:20pm PDT

Natalie Portman

Before she starred in movies such as Black Swan, Portman was just a pouty, photogenic little lady.

Baby me #OldHeadshotDay

A post shared by Natalie Portman (@natalieportman) on Apr 28, 2018 at 10:57am PDT

Matt Damon

Since Damon isn’t on Instagram, his best buddy Ben Affleck kindly posted pics of his friend’s early headshots, which looked strikingly similar to a GQ photo shoot. Of course, Affleck didn’t share any of his own vintage snapshots.

Ben Stiller

Do you even recognize the star of There’s Something About Mary in this photo? Neither do we.

Naomi Watts

The Aussie star noted her many freckles and thicker eyebrows in her headshot pic.

Bushy eyebrows and freckle faced #oldheadshotday xx

A post shared by Naomi Watts (@naomiwatts) on Apr 27, 2018 at 7:36pm PDT

Ian Ziering

Seriously, this guy was born to play Steve Sanders on Beverly Hills, 90210.

Leslie Jones

The Saturday Night Live comedian admitted that she had attempted to look a lot like a certain Ghost star in her first acting photos.

Leah Remini

Before Remini shook things up on Who’s the Boss and Saved by the Bell, she posed for this sweet photo.

Tiffani Thiessen

Another Saved by the Bell alum shared a snapshot from one of her first modeling shoots, which appears to have taken place around the time she enrolled at Bayside High.

Tori Spelling

Even though her dad was mega-producer Aaron Spelling, she still had to submit a photo at auditions. The 90210 alum looks so different with darker hair!

Emma Watson

Who knew the future Hermione Granger had a thing for pink … and for baking? Ha.

Billy Eichner

The jokester posted a photo of his awkward years with the hashtag for old headshots.


A post shared by Billy Eichner (@billyeichner) on Apr 27, 2018 at 2:54pm PDT

Viola Davis

If you’re wondering why Davis looked so happy in this vintage photo, it’s simple: She was totally feeling herself!

I was feeling myself during this shoot. #OldHeadshotDay

A post shared by Viola Davis (@violadavis) on Apr 27, 2018 at 8:37pm PDT

Rebecca Romijn

When the model began acting in the late ’90s, she was married to actor John Stamos. In case you forgot that they’re no longer together and that she married actor Jerry O’Connell in 2007, someone helpfully crossed out the last name she used during the marriage.

#oldheadshot @thestevewillis

A post shared by Rebecca Romijn (@rebeccaromijn) on Apr 27, 2018 at 5:49pm PDT

Mayim Bialik

Before she starred on Blossom, Bialik was just a blue-eyed, blonde-haired gal — without a floppy hat! — looking for a job.


A post shared by mayim bialik (@missmayim) on Apr 27, 2018 at 5:15pm PDT

Kelly Ripa

The talk show host’s ’80s look helped her swing a role on All My Children that lasted 20 years.

Is this really a thing? #oldheadshotday

A post shared by Kelly Ripa (@kellyripa) on Apr 27, 2018 at 7:56pm PDT

Kim Cattrall

Pre-Samantha Jones, Cattrall was a brunette.

#oldheadshotday Central Park, NYC. One week before graduation 1974

A post shared by Kim Cattrall (@kimcattrall) on Apr 28, 2018 at 2:18pm PDT

Drew Barrymore

The offspring of the famous Barrymore family began acting as an infant, partly thanks to this cute snapshot.

#oldheadshotday I’m joining in on the fun.

A post shared by Drew Barrymore (@drewbarrymore) on Apr 28, 2018 at 6:53pm PDT

Molly Shannon

Shannon, a future SNL star, was willing to get dramatic for her big break.

Anthony Anderson

Black-ish star Anderson began his journey into stardom with a too-cool-for-school look to remember.

Octavia Spencer

The generous Oscar winner used her old headshot to pay tribute to all those who helped her as a struggling actress.

Nick Jonas

Apparently, you even need a professional photo to be in a band with your brothers. Joe and Kevin had one too.

So there’s this… #oldheadshotday

A post shared by Nick Jonas (@nickjonas) on Apr 28, 2018 at 2:54pm PDT

#oldheadshotday signed and ready to go

A post shared by J O E J O N A S (@joejonas) on Apr 28, 2018 at 2:45pm PDT


A post shared by Kevin Jonas (@kevinjonas) on Apr 28, 2018 at 3:14pm PDT

Jessica Biel

Check out that scrunchie in the future Mrs. Timberlake’s hair!

Just going to leave this here #OldHeadshotDay

A post shared by Jessica Biel (@jessicabiel) on Apr 28, 2018 at 4:20pm PDT

Kathy Griffin

Notice anything different about Griffin’s face? According to the funny lady, you should.

Penélope Cruz

We now know definitively that, yes, Cruz always looked perfect.

Gabrielle Union

Union’s cute snapshot helped earn her early roles as the unnamed “Mall Girl” on Family Matters and Ashli on Moesha.

Kristen Bell

Baby Bell could really bring the drama!

Russell Crowe

Crowe felt compelled to point out that he was more than just another pretty face.

Just to help , I’m actually pointing my head out for you for #OldHeadshotsday

A post shared by Russell Crowe (@russellcrowe) on Apr 29, 2018 at 6:50pm PDT

Vanessa Hudgens

The crew behind High School Musical liked what they saw in Hudgens’s angelic photos so much that they cast her as high schooler Gabriella Montez in the Disney hit.

I guess it #oldheadshotday ? Lol here’s a few of my best

A post shared by Vanessa Hudgens (@vanessahudgens) on Apr 28, 2018 at 8:27pm PDT

Amy Schumer

Leave it to Schumer to crack a joke, even when she’s recovering from a kidney infection that put her in the hospital.

#oldheadshotday #kidney #balmain

A post shared by @ amyschumer on Apr 27, 2018 at 8:51pm PDT

Joe Manganiello
#OldHeadShotDay Circa: 2000 : Becky Thurner
A post shared by Joe Manganiello (@joemanganiello) on Apr 27, 2018 at 11:41am PDT

It’s understandable if you didn’t recognize Sofia Vergara’s hubby at first glance. In the headshot he shared from nearly 20 years ago, Manganiello looked a lot different than he did in Magic Mike or Justice League, although the hairstyle was similar to what he has going on today.

Reese Witherspoon

Witherspoon poked fun at her early snapshots, but the truth is that they worked. Two years after they were taken, she nabbed her first role, in the movie The Man in the Moon, which earned her rave reviews.

Melissa McCarthy

Pretty sure McCarthy was making people laugh long before Bridesmaids, thanks to her tiny cowboy hat and tiny cowboy boots.

Gabourey Sidibe

Seriously? Sidibe’s homemade snapshot rivaled the quality of the others.

Sarah Michelle Gellar

Gellar began acting when she was 4, so, yeah, her headshots are pretty dated. They’re also adorable and sent her on a career that’s lasted decades.

Busy Philipps

Philipps might not have gotten any jobs with her headshots, but they’re fantastic fodder for her beloved Instagram feed.

Peter Facinelli

#oldheadshot day. #fbf

A post shared by Peter Facinelli (@peterfacinelli) on Apr 27, 2018 at 1:17pm PDT

Do you think it was this shot that helped Facinelli earn his role as the popular jock in Can’t Hardly Wait a few years into his career?

Eric Stonestreet

The Modern Family actor rocked an English professor look in his early days.

Ali Larter

Been at this game for awhile! #oldheadshotday #tbt

A post shared by Ali Larter (@alilarter) on Apr 27, 2018 at 1:01pm PDT

Actually, Larter looked pretty similar to the way she looks now in the vintage headshot she posted.

Brittany Snow

Snow was acting by the time she was 8, and by the time she was a teenager, she was a regular on Guiding Light. The Pitch Perfect actress must have several headshots in old photo albums, but she chose to highlight a painting of herself as a little girl. While Snow referred to it as “terrifying,” she can take comfort in the fact that everyone who was alive in the ’90s will totally get it.

Check out more early headshots of the stars here.

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