The song “Teenage Dirtbag” sung by Wheatus in 2000 perfectly encapsulated the cringy and awkward teenage experience. Although it gained some popularity at the time, it has recently become a viral trend on TikTok where people film themselves now and then show pictures of their teen selves. Even celebrities have gotten in on the fun, and here are a few who definitely were teenage dirtbags!
Ashton Kutcher Now
It’s quite astonishing to realize that Ashton Kutcher, one of the most adored Hollywood actors, has been active in the industry for more than two decades. However, this is an accurate statement since his career commenced in 1998.
Unfortunately, his recent appearances in the news have been related to his health problems. He has been open about his battle with an uncommon medical condition known as vasculitis. However, he is scheduled to make a comeback in his original character’s sequel, That ’90s Show.
Ashton Kutcher Then
During his teenage years, Ashton had a deep passion for theater despite being involved in minor legal issues. He once attempted to steal money by breaking into his high school, which resulted in a burglary conviction.
Although he completed 180 hours of community service and was on probation for three years, it did not prevent him from being an avid partygoer during his college years which resulted in him getting evicted from his apartment. However, this event led him to start modeling and ultimately landing a significant role in the sitcom That ’70s Show.
Miley Cyrus Now
Miley Cyrus has led a very eventful and exciting journey. Though her acting career has seen ups and downs, her music career has been a major triumph. She has been a prolific artist, having accomplished seven studio albums, four EPs, three live albums, and 36 singles—all before turning 30!
Miley’s romantic experiences have been diverse as she is openly pansexual and has been involved with individuals of all genders throughout the years. She believes that she is ready to love anyone who accepts and appreciates her for who she is. She was in a 10-year-long relationship with actor Liam Hemsworth, which ended in 2019.
Miley Cyrus Then
Miley’s phase of being a “teenage dirtbag” has gained notoriety over time, largely because we witnessed her grow up before us. She transitioned from being known as Miley, the child who loved music and happens to be Billy Ray Cyrus’s daughter, to the famous teenage sensation, Hannah Montana.
As Miley gained more recognition, she distanced herself from her clean-cut image as a Disney Channel star and embarked on a journey of self-discovery, which resulted in her being surrounded by controversy. Despite this, she was still able to appeal to her fans, even during her most unconventional moments.
Jake Gyllenhaal Now
Although Jake Gyllenhaal’s parents were notable figures in the industry, he has also demonstrated exceptional talent and adaptability as an actor in his own career.
Jake Gyllenhaal has appeared in numerous movies such as Donnie Darko, Brokeback Mountain, Zodiac, Prince of Persia: The Sands of Time, Spiderman: Far From Home, and many more. In terms of his personal life, he has been romantically involved with several well-known women in the past, such as Kirsten Dunst, Reese Witherspoon, and Taylor Swift. Since 2018, he has been in a relationship with French model Jeanne Cadieu.
Jake Gyllenhaal Then
Jake’s debut as the titular character in Donnie Darko effectively portrayed his “emotional teen” persona. He had already started his acting career earlier thanks to his parents’ connections in the industry.
Nevertheless, it was his parents who prevented him from pursuing his acting career at an earlier stage. Although they gave him permission to participate in auditions, they often refused to let him take the roles even after he was selected. As a result of their actions, he also took up temporary jobs as a lifeguard and a busboy at a nearby eating establishment.
Zac Efron Now
Zac Efron has successfully transformed from a popular teen idol to a respected actor, surpassing his earlier work at Disney. Although initially typecasted in comedic films such as “Neighbors”, “Dirty Grandpa” and “Mike and Dave Need Wedding Dates”, he has broken out of that mold and has secured more substantial acting opportunities.
The actor has had a tough time in the past few years, with rumors of cosmetic procedures circulating about him. However, he has now disclosed that he suffered a broken jaw in 2021. He is currently recovering and preparing to return to filming, while staying on a private property in Australia.
Zac Efron Then
Although he played a jock in the High School Musical trilogy, Zac characterized himself as somewhat of a nerd, displaying intense reactions when receiving grades below an A. In addition, he had an immense interest in musical theater, and was involved in singing lessons and performing in nearby shows.
When he started a romantic involvement with Vanessa Hudgens in 2007, he definitely caused heartbreak among his teenage fans who idolized him. Although he separated from her in 2010, he continues to be adored by young adolescent girls and women, despite no longer fitting in the “teen” category himself.
Kristen Stewart Now
Kristen Stewart’s journey in the entertainment industry has been quite intricate. During her early years as an actress, she faced criticism and mockery for her lack of expressiveness and for being constantly associated with the Twilight Saga. However, it was only when she transitioned from mainstream films to independent productions that her true potential as an actor was finally recognized.
Her recent performances have earned her the recognition that she deserves for her talent. On the romantic front, she has been in a joyful relationship with Dylan Meyer – a screenwriter, since 2019 and the couple got engaged at the end of 2021.
Kristen Stewart Then
During her teenage years, Kristen was lucky enough to land one of the most sought-after roles in Hollywood, although it later became controversial. Being chosen to play Bella Swan had a significant impact on the actress, as she suddenly became hugely popular with young people practically overnight.
In the first movie of the saga, Chatrine Hardwicke, the director, characterized Kristen as a shy and slightly awkward teenager. This quality actually contributed to her suitability for playing the female protagonist.
Taylor Swift Now
With her remarkable talent and exceptional performances, Taylor Swift has gained an enormous following, possibly making her one of the most prosperous music artists, regardless of gender, in recent years.
She is not just an exceptional musician, but she has also impacted numerous young female artists and entire music genres like pop and country. Additionally, a millipede was named after her as a new species.
Taylor Swift Then
Taylor’s current status as a highly regarded artist was not always the case. During her early years, numerous critics ridiculed her as a country singer and songwriter, possibly due to her popularity mainly among young girls.
Frequently, she became a target of ridicule for composing melodies about her former partners. However, such foolish critiques hold little significance when you are among the top performers globally at the age of 20!
Ryan Gosling Now
Ryan Gosling is indisputably among the most debonair and captivating male actors in contemporary Hollywood. He transitions effortlessly between romantic, comedic, action-packed, and emotionally-driven roles.
His portrayal of romantic characters in movies such as The Notebook, Crazy, Stupid, Love, and La La Land, has made him a popular and adored romantic hero. This is surely appreciated by his partner, Eva Mendes.
Ryan Gosling Then
Ryan didn’t possess the same level of ease and self-assurance as an actor in the past, his journey wasn’t always smooth. During his childhood, he was a victim of bullying and found it challenging to keep up with his studies. Consequently, his mother decided to homeschool him for a year until he felt confident enough to rejoin school.
During his adolescence, he gained fame as a young performer on various children’s television programs, including The Mickey Mouse Club and Goosebumps. Nevertheless, at the age of 12, he was asked to leave The Mickey Mouse Club as he was perceived to have displayed an overly confident and arrogant demeanor.
Leonardo DiCaprio Now
The career of Leonardo DiCaprio has been impressive to date, considering his early years as a child actor. He is frequently chosen for serious, emotional, and dramatic roles in movies, and has delivered great performances in several films such as The Departed, Shutter Island, Inception, The Great Gatsby, The Wolf of Wall Street, among others.
Although Leo is extremely devoted and enthusiastic about his profession, he shows little interest in revealing his personal life. He seldom accepts requests for interviews and prefers to maintain his privacy. However, this does not prevent the media from making outrageous conjectures about his love life.
Leonardo DiCaprio Then
When Leo was younger, he was considered one of the most popular teenage heartthrobs. He explained that several factors influenced his decision to pursue acting, including his dislike for public school and his preference for auditions. Additionally, he wanted to support his family financially.
As a result of portraying significant characters like a brooding adolescent and a charming romantic figure in the highly popular films Romeo+Juliet and Titanic, he became the object of desire for almost all teenage girls (and some women) as a celebrity heartthrob.
Freddie Prinze Jr. Now
Although Freddie Prinze Jr.’s acting career has been gradually declining for the past 10 years, his diehard fans still hold him dear due to his earlier work in the 1990s as well as his later memorable roles.
He is mostly known for playing the character of Fred Jones in the Scooby-Doo films alongside his wife, Sarah Michelle Gellar. Additionally, the couple has two children and he has a strong passion for Brazilian Jiu-Jitsu.
Freddie Prinze Jr. Then
According to reports, Freddie’s high school experience had a significant impact on his passion for acting. It appears that Neil Patrick Harris visited the school to inspire students to pursue acting, which had a strong influence on Freddie.
Naturally, the opportunity that catapulted him to fame was his involvement in popular movie franchises aimed at teenagers, including both the original and sequel versions of I Know What You Did Last Summer. He gained immense popularity among young audiences when She’s All That hit the screens in 1999, highlighting his ability to portray romantic characters.
Kylie Jenner Now
Kylie Jenner is undoubtedly one of the most prominent celebrities globally. With 455 million followers on Instagram as of 2022, she is the most followed woman on the platform, ranking second only to Cristiano Ronaldo.
In addition to being a highly accomplished entrepreneur who runs her own cosmetics business and a number of prosperous fashion brands, she has managed to maintain her standing as a notable public figure and a dedicated parent, despite having faced numerous controversies.
Kylie Jenner Then
Due to the widespread popularity of Keeping Up With the Kardashians, Kylie was consistently exposed to public scrutiny, which resulted in most of her teenage growing pains being captured by the cameras.
When she became 18, her lip injections garnered a lot of attention. She later revealed that the reason she did it was because a boy made a remark about her having tiny lips, which made her feel self-conscious.
Chris Evens Now
Over the last ten years, Chris Evans has emerged as one of the most successful actors in Hollywood due to his transformative portrayal of Captain America in the Marvel Cinematic Universe.
Fortunately, he has worked on numerous other films that demonstrate his outstanding skills and adaptability, going beyond his role as the First Avenger. His ability to master comedy and drama is particularly noteworthy, as evident in Scott Pilgrim vs. the World or Knives Out.
Chris Evens Then
Although his acting role in Not Another Teen Movie was considered a ridiculous parody that received negative reviews from critics, Chris takes pride in his performance and finds it amusing.
During an interview, he expressed his excitement about being a part of the movie and didn’t consider it as an artistic compromise. This perspective continued during the Fantastic Four movie which unfortunately failed.
Paris Hilton Now
Over the past two decades, Paris Hilton’s celebrity career has been remarkably intriguing. Initially perceived as a superficial blond model and socialite, she has managed to establish a solid business empire as a conscientious entrepreneur.
She is not only talented in acting, singing, and writing, but she is also a successful entrepreneur in social media and other business ventures. Even though she was once known for her popularity without any real merit, she has now demonstrated that she is a significant player in her field.
Paris Hilton Then
Paris had already made a name for herself in the world of celebrities long before the Kardashians even came into the picture. Her lively and vivacious persona as a “party girl” was unprecedented and she can be considered as the pioneer influencer who began setting trends that were religiously followed by most teenage girls during that era.
Due to her “It Girl” status, she faced a lot of scandals and controversies, such as the well-known tape that was released in 2001, as well as several legal issues over the years.
Aaron Paul Now
It’s impossible to mention Aaron Paul without acknowledging the importance of his role in a highly regarded and beloved show from the past twenty years. Despite gaining recognition from his part in HBO’s Big Love, it was Breaking Bad that truly launched his career.
After the last episode of Breaking Bad, he and his co-star Bryan Cranston became so close that they even got matching tattoos. They still have a strong bond and even run a business together, taking advantage of any chance to collaborate.
Aaron Paul Then
Ever since Aaron participated in local theater productions at a young age, he has been captivated by acting. It appears that he didn’t find the remaining years of school very engaging because after graduating, he used all his savings to drive with his mom to LA.
Although Aaron’s real-life personality is quite different from Jesse Pinkman’s character, it appears that they were both influenced by the unappealing teenage fashion of the “dirtbag” era in the early 2000s.
Joe Jonas Now
Currently, it appears that Joe Jonas’ focus is primarily on his lovely family. Joe has been in a relationship with Sophie Turner since 2016, and they got married in 2019. They welcomed their first child into the world in 2020.
In 2022 summer, they had the pleasure of having another baby girl join their family. As for his career, he is occupied with the revival of the Jonas Brothers and with his comeback to acting through the movie Devotion.
Joe Jonas Then
Joe gained fame during his teenage years as a member of the popular band, the Jonas Brothers. Along with his siblings Kevin and Nick, the trio achieved success, which led to appearances on Disney Channel.
As a result, the brothers were featured in the Disney Channel film, Camp Rock, alongside Demi Lovato. Although the movie may appear embarrassing today, it unquestionably gained a substantial following at the time of its debut.
Ariana Grande Now
Ariana Grande’s distinctive voice has been impossible to ignore for those who have tuned in to the radio recently. Her unparalleled vocal range spanning four octaves, coupled with her exceptional style, has propelled her to the forefront of the music industry.
She’s also incredibly influential as an artist and as a social media personality. She has also broken over 22 Guinness World Records by having some of the most popular songs of all time!
Ariana Grande Then
Ariana was just 15 when she landed her first role on Broadway. But, her first major success came as the silly and innocent Cat Valentine on Nickelodeon’s Victorious and Sam & Cat.
Her iconic red hair for the show actually severely damaged her hair, which is why they eventually had to resort to wigs to keep Cat as a redhead. Her time on Sam & Cat recently made headlines due to her former co-star’s memoir.
Ryan Reynolds Now
Since much of Ryan Reynolds’ career began with comedy (Van Wilder, we’re thinking of you), it’s not really surprising that he has now become the king of wild comedy movies. But, did you know he actually played his most iconic character before Deadpool came out?
In X-Men Origins: Wolverine, he actually appears in several scenes as Wade Wilson/Weapon XI. Sadly, in that movie, his character’s mouth was sewn shut. After fighting for it for several years, he finally got the green light to produce Deadpool and give it the treatment it deserved.
Ryan Reynolds Then
Although it might feel impossible to believe seeing as he’s so big now, Ryan actually started his career on Nickelodeon’s teen soap opera. Hillside (known as Fifteen in the US) ran for three years in the early ‘90s and had Ryan play Billy Simpson.
The teen star life didn’t suit Ryan, and he actually decided to quit acting after the show ended (which lasted until the 2000s). As an alternative job, Ryan worked for a while in both a warehouse and a restaurant.
Christina Aguilera Now
Vocally, Christina Aguilera is probably one of the most impressive singers of the past two decades — often compared to Whitney Houston, Celine Dion, and Mariah Carey. She’s had tons of hits and is a triple threat as she’s an incredible vocalist, dancer, and actress.
She’s had quite a bit of criticism flung against her over the years, mostly regarding her extravagant and very revealing fashion style. In response to those claims, she stated, “Just because I have a certain image, everyone wants me to be this role model. But, nobody is perfect, and nobody can live up to that.”
Christina Aguilera Then
Christina’s started pretty early on as she won her very first talent show at the age of eight. From there, her incredible determination and drive pushed her toward stardom. But, despite wanting her first album to be of soul music, she had to settle for “bubblegum pop.”
That’s mainly due to Britney Spears’ immense popularity in the pop music scene. In fact, Christina has had to struggle with being compared to Britney throughout her early career (and even later). Britney even beat Christina to The Mickey Mouse Club by two years!
Gwen Stefani Now
Anyone growing up in the late ’80s and ’90s could have possibly missed the incredible popularity of the American rock band No Doubt, and their incredible lead singer Gwen Stefani. She has also managed to create an incredibly successful career as a solo artist.
In 2022, she launched her own beauty brand called GXVE Beauty. She’s now also married to fellow musician Blake Shelton, and they’ve even collaborated on several songs and projects together. She has three children.
Gwen Stefani Then
It’s actually all thanks to her brother, Eric, that Gwen became the icon she is, as he is the one who introduced her to what was then a ska band, No Doubt. He played the keyboards there before leaving for a career in animation.
Gwen cited Blondie singer Debbie Harry as a massive influence on how a female rock star should be. Certainly, no one can argue with the massive success that the band found once they changed directions from ska to songs like “Don’t Speak.”
Cole Sprouse Now
Cole Sprouse has had an interesting post-child star career so far. Despite his interest in acting, he chose to go to college and majored in Geographic Information Systems in Archaeology. Once he finished his degree, he returned to the screen.
Thanks to his role as Jughead Jones in Riverdale, his transition into more adult acting has been pretty successful. He has also managed to leverage himself as a romantic teen lead with movies like Five Feet Apart and Moonshot.
Cole Sprouse Then
Cole had an immensely successful child star career alongside his twin brother, Dylan. In fact, they started acting at the very young age of eight months! As young children, two of their most famous roles were in Big Daddy and as Ross’ son, Ben, in Friends.
But, of course, it was his work on the Disney Channel as Cody Martin that made him a household name (at least, in houses with children). Possibly thanks to the Disney Channel’s extremely strict code of conduct for young stars, Cole has always been considered pretty wholesome.
Hilary Duff Now
Hilary Duff has basically done everything. She’s a recording artist with several successful albums out, she’s acted in many movies and TV shows, and she’s even a published author — having written a young adult trilogy alongside Elise Allen.
She’s currently starring and producing the spinoff series to the beloved How I Met Your Mother, called How I Met Your Father. She’s also a mother herself, raising her three children alongside her husband, Matthew Koma.
Hilary Duff Then
Though many might remember her from her generation-defining role as Lizzie McGuire in the Disney Channel show by the same name, her career began several years before that with many commercial roles and several acting gigs.
Thanks to her teenage fanbase, Hilary’s public image remained fairly childish for a long time (while acts like Britney Spears and Christina Aguilera were marketed to more “mature” fans). She still made the transition into more adult content, but with a lot less controversy surrounding that change.
Lindsay Lohan Now
After years of struggles, Lindsay Lohan is actually now back in the public eye as she returns to acting. In 2021, she signed with Netflix to act in several movies, including a Christmas film that should be coming out at the end of 2022.
She has returned to music as well, coming out with a new single after 12 years in 2021 called “Back to Me.” She’s also now apparently happily married to her long-time partner, Bader Shammas. We can’t wait to see what else she has in store for the future.
Lindsay Lohan Then
Lindsay Lohan’s wild years certainly earn her the “teenage dirtbag” title, and not just in looks. Starting off as a child star, she became a true teen idol thanks to the massive popularity of the cult film, Mean Girls.
Unfortunately, the added pressure of her fame and the subsequent paparazzi attention made Lindsey slowly turn to illicit substances and problematic behaviors. As her career progressed, she became more and more known as a wild star. It has taken years for her to rebuild her brand and her career from those troubles.
Jared Leto Now
Jared Leto is an incredibly versatile actor and he is often described as disappearing into his characters. Many credit this to his method acting, which has actually come under fire in recent years for apparently making him difficult to work with.
His recent roles in the ever-expanding superhero genre (Morbius and the Joker) have also been heavily criticized for their poor quality and over-the-top acting. Still, he’s regarded as extremely talented.
Jared Leto Then
Jared’s early life wasn’t easy, as his parents underwent a difficult divorce, and his father passed when Jared was eight. His mom later lived a fairly hippie lifestyle, encouraging her sons to go into the arts.
Jared and his brother Shannon took that to heart and played together, later forming the beloved band, 30 Seconds to Mars. On the topic of his adolescence, the star has said, “There wasn’t a clear line that was drawn. We celebrated creative experience and creative expression. We didn’t try and curtail it and stunt any of that kind of growth.”
A new holiday has hit the social media scene: #OldHeadshotDay and celebrities are giving us throwbacks from funny to adorable to embarrassing to gorgeous. Emma Watson is best known for her major part as Hermione Granger in Harry Potter. On top of her successful acting career, she is also an enthusiastic activist for women’s rights. Despite Emma sarcastically captioning, “I’m REALLY glad this picture of me wearing a baker’s hat exists!” we think she looks as stunning as ever.
Sarah Hyland was born in New York City in 1990 and attended the Professional Performing Arts School in Manhattan, destined for an acting career from a very young age. She is most well known as Haley Dunphy, her character from the U.S. sitcom Modern Family. On Headshot Day, Sarah released this adorable picture of herself at 5-years old comparing it to the equally cute Prince George. To be fair she must have some royal blood as the resemblance is uncanny.
Accompanied by the simple caption, “Baby me,” Natalie Portman could not look any cuter in her Headshot Day photo. The talented actress born in Jerusalem in 1981 clearly had beauty before the fame. From age four, Portman performed as a dancer. By 10, she was asked to become a child model, which she turned down to focus on acting. In an interview, Portman said she was “different from the other kids. I was more ambitious. I knew what I liked and what I wanted, and I worked very hard. I was a very serious kid.”
In an attempt to embarrass his best pal, Ben Affleck released these headshots of Matt Damon saying, “I know this is a day late, but Matt isn’t on Instagram so thought I’d help him out.” Posting a cute, playful picture of Matt doing up his tie, as well as a topless picture of him covering his chest, Affleck received much attention from these snaps of his childhood friend. American actor, film producer, and screenwriter, Matt is one of the highest-grossing actors of all time.
Ellen Degeneres is an extremely popular household name. Many sit down weekly to watch her host her own TV show called The Ellen Degeneres Show where she hosts and interviews many A-list celebrities. While her voice may be recognizable to all as Dory from Finding Nemo, her face has barely changed since this headshot that she released on Instagram. The LGBT star is best known for her comedy value and this headshot certainly sums up her bubbly personality.
On Headshot Day, this cute yet mischevious grin posted by Ben Stiller was accompanied by an equally funny caption, “Special skills: juggling, scuba diving, tap dancing and drums. Commercials on request.” Born into a house of comedy and acting, his mother Anne Meara, showed him the way and at nine years old gave him the chance to star on her short-lived television series, Kate McShane. After that and many parts performing with the NYC’s First All Children’s Theater, Stiller kicked off his lifelong career.
Melissa McCarthy posted two headshots which must have used to for very different roles. She has featured in many TV sitcoms such as Gilmore Girls and Mike & Molly, and movies such as Bridesmaids, all leading her to her title as a two-time Primetime Emmy Award winner. Sharing these hilarious throwbacks she said, “If you can’t handle my scowling headshot you don’t deserve my tiny cowboy hat headshot.” Interestingly, she failed to mention the tiny cowboy boot earrings too!
We have to give Viola Davis credit for her sense of humor as she embraced her embarrassing headshot by captioning, “I was feeling myself during this shoot.” The American actress and producer is the first black actress to be nominated for three Academy Awards, winning one, and is the only black person to achieve the Triple Crown of Acting (an Oscar, an Emmy, and a Tony). Despite what her headshot depicts, she was listed by Time Magazine in 2012 and 2017 as one of the 100 most influential people in the world.
Landing his first job as ‘Flash Thompson’ in Spider-Man (2002), Joe went on to feature in an entire five seasons of the series True Blood. Since this headshot in 2000, Joe’s good looks have not faded and a decade later he was cast as Big Dick Richie in Magic Mike, a film about a young male stripper. He is married to the beautiful Modern Family star, Sofía Vergara. Giving credit to the photographer of this picture in his Headshot Day upload, Joe had nothing much more to say about his smoldering picture.
Reese Witherspoon, with her wide smile and big eyes, is easily recognizable in this 12-year old headshot. Including a checklist in her caption, she ticks off having a “Parasol, Top pony, Sassy smile, Cut off Jean overalls, 12-year-old confidence and I’m currently a much more impressive 5’2 now…”. An extremely popular actress and winner of many awards such as a Primetime Emmy Award, a BAFTA Award, and a Golden Globe Award, she was destined for her acting success at an early age.
“My attempt at side ponies, attitude, and a bit of croquet,” Kristen posted next to her upload of these gorgeous headshots. As a young child, Kristen was certainly not shy of the attention and knew just how to work the camera. Her mother, with a keen interest in her acting career, made sure Bell was established with an agent before she was 13. From this, she appeared in newspaper advertisements for several Detroit retailers and television commercials. She began private acting lesson and has scored herself major roles ever since.
“Why so serious, twenty two year old Jen?” Jennifer asked herself as she posted this stunning headshot to Instagram. Despite not yet appearing on TV at a young age like many other actors, she was not shy of the stage. Instead of focusing on her studies, she always wanted to perform. She participated in musicals at the local community theater and took piano, singing and ballet lessons. Ben Affleck, poster of Matt Damon headshot, and Garner were married in 2005 and had three children, but separated in 2015.
Best known for his role as Jack McFarland on Will & Grace, Sean Hayes found his success. From the show, he has won an Emmy Award, four SAG Awards, and one American Comedy Award, and earned six Golden Globe nominations. Before kickstarting his acting career, Hayes studied Piano performance and worked as a classical pianist. In 1995 he moved to LA and began work as a stand-up comedian and actor. Posting the headshot a day late, he shared his contribution to his worldwide followers, releasing this complimentary photo of himself.
Captioning his picture, “The name’s Douchemaster McChest and this is my first headshot. You’re welcome,” Chris knows how to not take himself too seriously. The actor did not have it easy growing up and came from a struggling family. Pratt dropped out of community college and, after working as a discount ticket salesman and daytime stripper, he ended up homeless. At 19 years old, Pratt was discovered by director Rae Dawn Chong whilst working as a waiter at the Bubba Gump Shrimp Company restaurant. She cast him in a short horror film, Cursed Part 3. His life changed from there.
This celebrity is easily the most recognizable from her childhood headshots. After posting the very young headshot captioning, “I’m joining in the fun,” Drew proceeded to post another cheeky childhood photo. Coming from a family of actors and actresses, Drew was destined for a life of fame. She began her career at a tiny eleven months when she auditioned for a dog food commercial. She then starred as Gertie in E.T. the Extra-Terrestrial (1982), which made her one of the most famous child stars of all time.
Isla released her beautiful headshot with the hashtags, “#oldheadshotday #overpluckedbrows #sassyevenatthisage”. You would think the Australian actress and author, married to the hilarious comedian Sacha Baron Cohen, would be brave enough to post a more daring headshot than this attractive one, but nonetheless, she seems to be disappointed with the state of her eyebrows. Isla was making her first television appearances at the age of 9. She had a regular role in the Australian soap, Home and Away until she made the transition to Hollywood in 2002.
Famous for being funny, Kumail had to go for a less conventional headshot. Posting to Twitter, Kumail Nanjiani released this rather spooky picture of himself with a flame saying, “This was a high risk shoot. I almost set my unibrow on fire.” The Pakistani-American actor and comedian began his career speaking on a podcast. He made some small appearances on TV until his film breakthrough in 2017 where he starred in The Big Sick which he wrote with his wife.
Chloë Grace Moretz
This absolutely adorable headshot of Chloë was taken when she was around 5 years old. Moretz became interested in acting at a young age when she would help her brother read lines as he attended the Professional Performing Arts Scool. She began her career in the film industry at age seven, with early roles in The Amityville Horror (2005), (500) Days of Summer (2009), Diary of a Wimpy Kid (2010), and others. Her brother, Trevor is now her acting coach. Moretz has also had a successful modeling career.
Believe it or not, once upon a time, the princess was a struggling actress. This old headshot was taken of Meghan Markle around her mid-20s when her acting experience was only limited to two roles; her appearance on General Hospital in 2001 and her role on CBS’s sci-fi legal drama Century City in 2004. Unsurprisingly, the Duchess of Sussex herself did not release this picture, yet an anonymous Facebook user posted it online along with her resumé captioning, “Am I too late for #Oldheadshotsday?”
Nathalie posted this cute picture captioned, “Before braces, before tweezers, before my hair only grew out and still grew down… BUT just before one of the funnest experiences of my life when I did #TheLionKingWestEnd aged 10….” before continuing with a bundle of hashtags. Nathalie is an English actress who started her career as a young child in various West End productions. She is most recently and universally recognized for her role as Missandei in the fantasy series Game of Thrones.
Leslie Jones is an American comedian and actress, who is also a cast member on Saturday Night Live. On Headshot Day, she took to Instagram to post this Whoopi-looking picture saying, “National Headshot day!! My first headshot! I didn’t know s***!! Man I got a deal at a photography place in Pasadena I think lol. I look older than I do now!! I thought what would Whoopi do!! Lol @whoopigoldberg”. The funny star continued to hashtag referring to Whoopi ‘#shewouldnothavedonethisitellyou’.
Elizabeth Jean Philipps was given the nickname “Busy” because as a kid she was always moving. As well as many movie roles, she is best known for her supporting roles on the television series Freaks and Geeks and Dawson’s Creek. Busy jokingly questions the “crazy clown lipstick or my terrible haircut” in this headshot for her lack of child modeling jobs. She certainly blossomed, however, as before her acting career she worked the toy-fair circuit as a real-life Barbie.
Amy’s husband, Darren Le Gallo, shared this headshot photo to Instagram with a caption that will make many hearts melt, “Um…What to say here…cute then & cute now.” Despite training to be a ballerina, Amy sought out musical theatre as better suited. Adams did not have an easy breakthrough into her acting career, she would frequently audition for whatever parts came her way, but she was mostly given the roles of “the bitchy girl”. In 2007, Adams was given the lead role in the musical Enchanted.
Posting online, Gerard accompanied his handsome headshot with, “Thank you to the person who made sure that one strand of hair was perfectly out of place.” Ok, Gerard, that strand of hair was exactly what I was looking at. The sexy Scottish actor was not in the industry all his life. After studying law he gave it up to start an acting career in the mid-1990s. After struggling to get many acting roles, he moved to Los Angeles at age 30 and was hired for parts in Dracula 2000, Tomb Raider 2, and Phantom of the Opera.
Sawa started out as a children’s action toy spokesman. Not long after, he appeared in popular movies such as Little Giants and Casper. The Canadian actor has had many other acting parts and in 2000 he played Eminem in the music video “Stan”. From 2010 to 2013, he had a recurring role on the drama spy fiction series Nikita as Owen Elliot. Devon Sawa posted this cheeky headshot to Instagram with a humorous caption saying, “I still use this one for action auditions.”
Sarah Michelle Gellar
Sarah Michelle Gellar was spotted by an agent at only four years old in New York City and starred in the movie An Invasion of Privacy (1983). Her most widely known part is the role of Buffy in Buffy the Vampire Slayer (1997 – 2003) and she became recognized as one of the greatest female characters in U.S. television. Sarah posted these 3 beautiful headshots explaining, “Mine are so old….how old are they?!? So old…They are all in black and white (and in case you were wondering- Aussie sprunch spray was the secret to those sweet bangs)”
Johnny Knoxville is particularly famous for his ridiculous stunts and dangerous behavior on Jackass. However, it is hard to tell how mischevious he is from this innocent photo. The actor, film producer, screenwriter, comedian, and stunt performer released his picture saying, “Someone said it was old headshot day and although this isn’t an old headshot, hopefully, my sophomore high school photo will still be embarrassing enough.” Looking at this young boy, we wonder what sort of crazy antics he could have got up to in his school years.
Yolanda Hadid is the mother of famous models Gigi, Bella, and Anwar Hadid. The Dutch-American former model and television personality is best known as a star of the reality television show The Real Housewives of Beverly Hills. We think it is fair to say there is no embarrassment here as her old headshot is more than beautiful. Although indicating that she does not like her hair by captioning “Headshot circa 1988 when bangs were in…” Yolanda is working those bangs like no one else possibly could.
English actress and film producer, Naomi Watts, struggled to kickstart her career for many years. She appeared in a couple of commercials and an Australian television series until she made her breakthrough in 2001 when she featured in David Lynch’s psychological thriller Mulholland Drive. The now 49-year-old released her pretty and youthful headshot claiming she had bushy eyebrows and a freckled face. Although this may be slightly correct, she was still able to make it into People magazine’s 50 Most Beautiful People in 2002.
Colbert is best known for hosting the Comedy Central program The Colbert Report from 2005 to 2014 and the CBS talk program The Late Show with Stephen Colbert, which began in September 2015. His shows have been extremely high-rated and Stephen has gone on to win nine Primetime Emmy Awards, two Grammy Awards, and two Peabody Awards. Therefore, there is no doubt Colbert must be a happy many even though claiming, “I don’t remember ever being this happy in my 20s…”
“Before Donna, Before Bleach, Before Flatirons… This is my headshot when I was 14 years old. The same one I used when I went in to audition for Troop Beverly Hills and Saved By The Bell.” Although no bleach or flatirons, at the age of 17 Tori was given the role of Donna Martin on Beverly Hills, 90210, which was co-produced by her father. She was also cast in a few episodes of Saved By The Bell as Violet Bickerstaff. Tori then appeared in many made-for-television films and even wrote a best-selling autobiography.
This was captioned, “Myyyyyyy… I had NO clue and SO many f’s to give,” the latter most likely refers to the fact Union grew up with self-esteem issues relating to her appearance. Growing up, she believed that blonde women were the “ideal of beauty” and “if I looked nothing like that, then I must be ugly.” At age 19 she was the victim of a horrendous attack but, fortunately, not long after she landed many successful acting roles. She is particularly known for her role as a popular cheerleader in Bring It On.
Ballas posted these adorable pictures on old headshot day with the caption, “You’re Welcome.” This multi-talented charming child grew up to be a dancer, choreographer, singer-songwriter, and actor. He started his career at a very young age. At eleven he earned a scholarship at the Italia Conti Academy of Theatre Arts in London. In 2007 he became more of a household name after featuring continuously as a ballroom dancer on ABC’s Dancing With The Stars. During his time on the show, Ballas released his first solo CD HurtLoveBox in 2011.
After writing and playing the lead role of Rebecca Bunch in the comedy-drama series Crazy Ex-Girlfriend and writing a musical comedy album including a successful song about Ray Bradbury, there is no doubting that Rachel Bloom certainly has a funny bone. Posting two of the same photos to Instagram, with one slightly lower than the other revealing her pancake stomach, the actress, singer, and comedian wrote, “Turn to the second pic to ogle at my 18-year-old midriff #oldheadshotday #fastmetabolism #prebirthcontrol.”
Claiming she was attempting to look like Jaclyn Smith, Driver blamed her poor attempt on “no makeup or money.” Despite what she thinks, Driver still looks great in her old headshot from 1989, when she was around 19 years old. The English actress made her first debut in 1990 appearing in a TV advertisement for Right Guard deodorant. Seven years later she was nominated for an Academy Award for Best Supporting Actress and a Screen Actors Guild Award for her role in Good Will Hunting.
Despite not looking too different now, the English actor claimed his headshot was 43 years ago. Posing on the mud banks of the River Thames in Chiswick, London, Stewart’s career kicked off and continued for over almost six decades, including roles on stage, television, and film. Starting with the Royal Shakespeare Company, Stewart moved on to Amerian television and film in the ’80s, playing the role of Captain Jean-Luc Picard in Star Trek: The Next Generation and starring in the X-Men series, In 2010, Stewart was knighted by Queen Elizabeth II for services to drama.
Describing himself in his smoldering headshot as having, “Special skills: journaling, sensitivity, hair,” Zach Braff couldn’t look any cuter. As it was Zach’s life dream to become a filmmaker, maybe we can assume he was writing film ideas in his notebook which he is holding on to for dear life. Most well known for his role as JD from the popular TV series Scrubs, Zach also directed and wrote some episodes. As a director, he started a campaign known as the Kickstarter to finance his film, Wish I Was Here.
American actress and television personality, Danielle Fishel, is known for her role as Topanga Lawrence-Matthews on the 1990s sitcom Boy Meets World which she began to feature in at the age of 12. Danielle’s fame did not start there, in 1991 at the age of 10, Fishel was discovered in a community theater where she performed in two productions, The Wizard of Oz and Peter Pan. Posting her charming headshots to Instagram, Danielle captioned, “People ask me all the time, ‘Danielle, have you ever jumped in rollerblades?’ Today you have your answer.”
Almost coinciding with her birthday, Penélope took Old Headshot Day as an opportunity to thank her fans and followers for their birthday wishes, “On this #oldheadshotday I say thank you for all the #happybirthday wishes. Lots of love.” The beautiful Spanish actress and model started her career as a teenager, featuring in Spanish music videos and had other acting roles. Penélope’s great breakthrough came in 2001 when Cruz starred in films Vanilla Sky and Blow. After featuring in Vanilla Sky together, her and Tom Cruise became an item, which lasted three years.
Joseph Gordon-Levitt has not changed a single bit from this adorable headshot. Joseph, with his delightful baby face, got into acting as young as the age of six and featured in the films A River Runs Through It, Angels in the Outfield, and 10 Things I Hate About You. He was spotted at the age of four after playing the Scarecrow in a theatre production of The Wizard of Oz. When he was older, Joseph went to study at Columbia University, but shortly after dropped out to continue pursuing his acting career.
Presenting this charming photo to social media, Fred pointed out his mum styled his hair that day. Fred spent most of his childhood playing the young Kevin Arnold in the television series The Wonder Years (1988 to 1993). Fred received two Golden Globes and two Emmy nominations for Outstanding Lead Actor in a Comedy Series during his time on the show. At the age of thirteen, he was the youngest actor ever to receive these honors. Despite having a lovable face, Fred lent his voice to many animated shows and movies.