20 Embarrassing Celebrity Headshots From Before They Were Famous

Celebrity Headshots

Talent is overrated. Who you know will get you nowhere. Money does not talk. No, no, if you want to truly make it in Hollywood, you need one thing and one thing alone: a freakin' awesomely epic headshot. That's the ticket to success. That's the stuff careers are built on. Yet amazingly, some of our favorite stars have made it big despite having had some truly terrible ones. So maybe we have it all wrong. Mullets, chest hair, random accessories and the lot -- perhaps if you don't have a headshot that makes people stop in their tracks, take notice, and simultaneously be slightly confused, you might as well give up now.

The celebrities that follow elevated the headshot game to new levels of embarrassing. More than likely, these photos conjure feelings of regret today in the stars whose careers they once launched, but for the rest of us, they are endless fun. In the grand scheme of things, some old photos of celebrity faces don't amount to much, but it is nice to know that we're not the only ones who have made some horrible decisions in our lives.

Here are 20 Awesome Celebrity Headshots Before They Were Famous.

20 Rebel Wilson - Who Doesn't Love the '90s - or Softball?

Rebel Wilson Celebrity Headshot

These days, Rebel Wilson is known for her self-deprecating, slapstick comedy in such films as Pitch Perfect and Bridesmaids. But the Aussie apparently got her foot in the door of show business thanks to her other talent - holding softballs awkwardly. To be fair, there is a lot more going on here than some random sporting equipment. You could look at it forever and still see something new every time.

Any good headshot conveys the multifacetedness of its subject. She's sporty, classy (we know this because she is wearing the world's thinnest necklace), and a little bit gangster thanks to a well-placed graffiti wall. Seriously, was there anything cooler in the '90s than carelessly baggy Esprit T-shirts? We learn so much about Rebel from this one shot, but of course, all that takes a backseat to the softball in hand. Props are usually frowned upon in headshots, and thanks to Rebel Wilson, we now know why.

19 Adam Sandler - There's Nothing Funny About Afros

Adam Sandler Celebrity Headshot

To get into comedy, sometimes you have to show how tough you can be, which might explain why Adam Sandler took the juvenile delinquent route with his headshot. Actually, we're not sure Adam had anything on his mind here other than hair product and popping collars, but somebody saw something in the future SNL star, and it wasn't a punk who looked like he was about to slash your tires.

We can only assume this very photo landed Sandler the audition that led to his brief recurring role on The Cosby Show playing Smitty back in the early '80s. From there, he would become one of the most financially successful comedians in the industry, proving that even for the funniest of actors, headshots are very serious business.

18 Emma Stone - Don't Look Into Her Eyes

Emma Stone Celebrity Headshot

When you think eyeballs, you inevitably think Emma Stone. The Oscar-winning La La Land actress has some of the most memorable orbs in Hollywood. And thanks to her first headshot, we now know that they are also to thank for getting her there in the first place.

We're not sure if Emma was intentionally trying to use her snake eyes to stare into our souls, but we're pretty sure she now knows our deepest, darkest secrets. You can see why she made it big with a headshot like this. You're instantly hypnotized, making it impossible to not do anything those eyes command of you to do. Just like a solar eclipse, it's probably better if you don't look directly into them.

17 Judi Dench - Headshot of the Corn

Judi Dench Celebrity Headshot

After seeing this early headshot of Dame Judi Dench, it's amazing to think that she didn't star in more horror films. There's just something inherently disturbing about a young girl standing in the woods wearing an oversized priest's collar turning towards you with a crooked smile, as if to say, “I'm going to behead your children.” We know this is supposed to be an innocent photo of a budding actress in the English countryside, but all it accomplishes is making us terrified of going to the English countryside.

Note to self, when photographing people outdoors, do not stand directly in front of the sun. It will only make your subject have to squint, causing their eyeballs to be replaced with dark voids of nothingness that will haunt you for the rest of your life.

16 Jennifer Aniston - The Rachel Before Rachel

Jennifer Aniston Celebrity Headshot

Yep, this is the photo that helped Jennifer Aniston make it big as the star of Leprechaun 2. While she would never quite reach the heights of that role again, she didn't do so bad for herself, and today, she's the face of pretty much every beauty product and bottled water company in existence. But would she have made it onto all those billboards and posed for all those magazine photoshoots if this young girl had still been around?

Apparently, Jennifer thought not, because a few years after it was taken, in the earliest days of her stint on Friends, Rachel got a nose job and cut off of the mop she used to wear on her head. Was this the right decision? Probably, but we like to follow the motto that if it's good enough for Leprechaun 2, it's good enough for the rest of us.

15 Jack Nicholson - Who Says You Can't Cut Your Own Hair?

Jack Nicholson Celebrity Headshot

Jack Nicholson is the epitome of cool when it comes to Hollywood stardom. He's also one of the most unique characters in the business, with a strange, magnetic personality that is as unpredictably terrifying as it is disarmingly charismatic. Given all he's accomplished and done, both on and off the screen, if there is one thing you can't say about Jack, it's that he did things any other way but his way.

Which makes this early headshot so perfect, because you can just tell he doesn't give a crap what you think, or even if he gets whatever role this photo is being passed around for. Even at that young age, Jack Nicholson looked exactly like the type of guy that would dance with the devil in the pale moonlight.

14 Robert Downey, Jr. - Hangovers Make For the Best Headshots

Robert Downey Jr Celebrity Headshot

Before he was saving the world as Iron Man and cashing $100 million dollar checks, Robert Downey, Jr. lived a crazy lifestyle. His self-destructive cocaine addiction and booze drenched partying throughout the '80s and '90s often landed him in prison or passed out in grungy alleyways. At one point, he found himself in an LA County jail earning eight cents an hour scrubbing pizza pans.

One kind of gets the feeling though that all that nihilistic behavior that he so perfect portrayed early on in his career during such films as 1987's Less Than Zero (and would try so hard to recreate in his own life) could have been spotted in his earliest headshots. Looking stoned out of his mind and as if he had just stumbled into the photographer's studio after an all-night bender, Downey embodies the Hollywood party boy persona in one very messy shot. Then again, he could just have been acting the heck out that photo for his own bemusement. Thus is the genius of RDJ.

13 Sam Rockwell - Because Leather

Sam Rockwell Celebrity Headshot

Sam Rockwell is one of the most underrated actors in Hollywood. He's funny, talented, perfectly suited for any role and, judging by this early headshot, a former member of the Greasers. But not the type of Greaser that would crash his parents car or do a choreographed dance knife fight. He's the type of Greaser you would want dating you daughter or starring in your directorial debut. Which is exactly what George Clooney did when he cast Sam in Confessions of a Dangerous Mind.

But still, what's with that hair, you might ask. Well believe it or not, there was a time when actors thought the bigger your hair, the better the career. In Rockwell's case, amazingly, it worked. What is not as clear is why he is wearing a leathered button down shirt, something that is not amazing under any circumstance.

12 George Clooney - Because Mullet

George Clooney Celebrity Headshot

Has anyone accomplished more with a mullet than George Clooney? Today, he may be the rakishly cool, well-groomed actor of Ocean's Eleven fame, but a few years prior to landing his big break on E.R., back in 1984, George was sporting a whole different kind of “cool.”

Believe it or not, there was a strange and mystical time when people thought mullets were acceptable. What's more, some believe that by showcasing the fully glory of one's mullet, they would be all but guaranteed success in love, life, and job interviews. And who can blame them? One might even go so far as to attribute all of George Clooney's future success to his one-time mullet. Not us. But we're sure there's somebody out there that would, which is why, much to the chagrin of Mr. Clooney, this headshot proudly sits in the Mullet Hall of Fame.

11 John Stamos - Some Things Definitely Go Out of Style

John Stamos Celebrity Headshot

We've already had headshots interpretively perform the '80s and '90s for us, and thanks to John Stamos, we now know everything that went wrong with the '70s. The Full House star and ageless vampire basically took everything that was popular and shameful about that groovy decade and tried to recreate in one glorious hair infused headshot. It now acts as a historical reminder of why we should never go back in time.

Seriously, young John Stamos is too handsome for his own good -- and ours. Luckily, he tried to distract us away from his unnaturally amazing mane by stealing John Travolta's outfit from Saturday Night Fever and putting on a sunglass necklace. Hopefully, that is one fashion trend that will never come back in style.

10 Madonna  - Like a School Girl

Madonna Celebrity Headshot

In her first headshot, Madonna looks more like a school girl that got held back one too many times from her local Catholic school than the future Queen of Pop. This was taken in 1978, right after Madonna Louise Ciccone had moved to New York City and started studying dance. There is little in the way of a sign that that the Ms. Ciccone in this photo would, in a few years time, go on to dominate the '80s music scene and stand as one of the era's fashion icons.

But maybe there was just enough rebellion in that slim black tie and headband to show that she could one day be one of the greatest entertainers in the world, that she was doing more than just livin' on a prayer (see what we did there?).

9 Christina Applegate - Livin' On Her Hair

Christina Applegate Celebrity Headshot

Leather jacket? Check. Bright red lipstick? Check. Lions mane for hair? Double check. Was there ever anything more '80s than this headshot of Christina Applegate. Everything you ever wanted to know (and forget) about that time can be summed up in her pose and dress.

One thing's for sure, the future Married With Children star knew exactly how to make a bold impression. Amazingly, she seems to be simultaneously flipping off whoever's looking at her photo and threatening to punch them in the face, which anyone who lived through the '80s can tell, pretty much sums it all up. Applegate shows that if you want Hollywood to think you're a rockstar, you better have the hair to prove it. Then again, Christina Applegate's photo is not so much a resume for an actress, as it is a performance piece for most insane decade that ever was.

8 Jim Carrey - Don't Try To Figure Him Out

Jim Carrey Celebrity Headshot

Anyone who's watched recent Jim Carrey interviews or his mini-art documentary I Needed Color knows that the dude lives in a world of his own. A lot of the time, it seems like he's the only one in on the joke or story he's telling. Which isn't always a bad thing, just a very confusing one.

In part, this frenetic style is what made him such a comedy star so perfectly suited for roles such as Ace VenturaThe Mask, and Man on the Moon. It's also what made his early headshot so strange. With a fedora and cross-eyed printed shirt that probably makes sense to no one but Carrey himself, the slapstick funnyman is definitely saying a whole lot more than just, “I want you to someday pay me to talk with my butt. We'll just never know what that whole lot more is.

7 Kristen Stewart - Who Knew She Had a Smile

Kristen Stewart Celebrity Headshot

The Twilight star is known for a lot of things. Smiling is not one of them. While Kristen Stewart has gone on record saying that she does in fact have the ability to smile, we would never have believed her were it not for this headshot. While smiling might be socially acceptable in most circles, her vampire chums would surely be ashamed.

What is so amazeballs is that as a rule of thumb, people normally don't smile in headshots. If they do, its rarely with teeth and more of a “you'd be an idiot not to hire me” smirk. It all has something to do with adding an air of mystery, or something. You certainly aren't supposed to look genuinely happy in them. Yet here we are; when the rest of the industry is trying their hardest to look as emotionless as possible, that's the moment K-Stew decides to break out the pearly whites. How odd.

6 Marilyn Monroe - The Pre-Blonde Bombshell

Marilyn Monroe Celebrity Headshot

When Norma Jeane Mortenson decided to go from mildly successful modeling gigs to a career in the movies, she used some of her old photos to help pave the way. You can just tell with her deer in headlights look that this young girl has no idea what is about to happen to her, or her hair.

Early on, as evidenced in this shot, Monroe was typecast in “girl next door” roles. But then she met a hotshot talent agent by the name of Johnny Hyde who helped her go through a complete makeover (along with a little plastic surgery to boot) and she came out the other side as America's blonde bombshell - a person almost indistinguishable from the one seen in this headshot.

5 Denzel Washington - King Kong Has a Few Things On Him

Denzel Washington Celebrity Headshot

Some people try to look cool in their headshots. Some people try to look funny. Some try to look like they're not scared out of their minds that they just dropped out of college and drove 3,000 miles cross-country because they once got a round of applause for playing Peter Pan in a high school play. Then there's Denzel Washington.

You know from Denzel's headshot that he had yet to gain the confidence that was bigger than King Kong. While most try to play up to the camera, strike a mysterious pose, or hypnotize you into giving them a role like the aforementioned Emma Stone, Denzel tried to look as nerdy as possible. Of course, nerdy for Denzel Washington is still pretty damn cool, but you get the feeling with his blank stare that he's not really even sure why he's there.

4 Victoria Beckham - Side Pony Spice

Victoria Beckham Celebrity Headshot

Occasionally, you'll come across a photo of someone you know is super famous, but for the life of you, you cannot tell who it is. This might be the most challenging of them all. Anyone who can look at this headshot and spot that this is the same person that would one day star in a internationally recognized girl band, dominate the fashion world, and settle down with David Beckham deserves our a round of applause.

Young Victoria Adams (aka Victoria Beckham) was trying to make her way into the world of dance when she had this photo taken. From this alone, few could have predicted back that she would eventually go on to spice up the world with her moves, or that people would want to one day have their hair styled the same way as her.

3 Melissa McCarthy - Cast Me I'm Crazy

Melissa McCarthy Celebrity Headshot

For many, headshots are a serious business of serious looks and serious faces, to let serious people know how serious you are about working in their serious business. For Melissa McCarthy, headshots are an excuse to dress up like a deranged librarian and stick your tongue out at strangers.

Eventually, Melissa would go on to star in such hits as Gilmore Girls, Mike and Molly, Spy, and Bridesmaids. But before any of that, there was the librarian, and a tiny cowboy hat. Behind the scenes, Melissa, under the guidance of a shady agent, decided her best way to break in was by doing something called "character shots," a version of headshots where you act out a specific character type. We're not exactly sure who she's supposed to be here, but maybe that agent knew what he was talking about, because despite this brief glimpse of craziness, or perhaps as a result of it, she went on to great things.

2 Hilary Duff - Tiny Actors and Tiaras

Hilary Duff Celebrity Headshot

No offense to Hilary Duff, but this early headshot of her is terrifying. She looks like a sixty year old grandmother trapped in a six-year old's body, one who never learned to smile properly. There has always been something unsettling about kid beauty pageants, and the future Lizzy McGuire star's first headshot looks like a calling card for Toddlers and Tiaras, which we're pretty was not the intention. We hope.

Of course, we cannot be blamed for the poor decisions made by our parents, but that does not make looking at the indiscretions they inflicted upon us any less embarrassing. Especially when the end result is as scary as this. Has anyone ever looked more in pain taking a headshot than poor lil' Hilary Duff?

1 Chris Pratt - Guardians of the Galaxy Never Button Shirts

Chris Pratt Celebrity Headshot

Way back when, a 20-year-old Chris Pratt was looking to kick start his acting career and was on the prowl for headshots. Fortunately, one day, he found himself at a West Hollywood post office where a strange man came up to him and offered to take him to his home and shoot him. After a quick shower at the man's place, a wardrobe change and some hair tszujing, VOILA! The greatest headshot the world has ever known.

The story behind how Chris Pratt got his now infamous headshot is almost as amazing as the photo itself. Especially considering that when the “photographer” finished shooting, he gave Chris the film free of charge and sent him on his way without another word or ever seeing him again. Few headshots are as magnificent and serendipitous as this, and anyone looking to break into show business would be wise to channel the flowing locks, open shirt, and come hither stare of young Andy Dwyer. You may regret it afterwards, and feel a little dirty, but that's what it takes to become a Guardian of the Galaxy, apparently.


Have you found any other amazing headshots of celebrities before they were famous? Share them with us in the comments.

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