Here’s What These Celebs Looked Like in Their “Teenage Dirtbag” Phase vs. Now

It’s kind of incredible to remember that one of the most beloved Hollywood actors has been around for over 20 years. But, that’s exactly the case when it comes to Ashton Kutcher, whose career started way back in 1998.

He has sadly been making headlines recently due to a medical condition, though. He has shared his struggle with a rare blood vessel disease called vasculitis. Despite that, he is slated to return in the sequel of his first role — That ‘90s Show.

As a teen, Ashton was very much a theater geek. This, however, didn’t stop him from getting into a bit of trouble with the law — he broke into his high school in an attempt to steal money and was convicted of burglary!

The 180 hours of community service and three years of probation definitely helped straighten him out, although not enough to stop him from becoming a party animal in college and being thrown out of his apartment. Thankfully, that led to him modeling for cash and eventually lending his famous role on That ‘70s Show.

Miley Cyrus has had quite a wild career and life. Putting aside her acting work, which has been all over the map in terms of success, Miley’s music career has been a force to be reckoned with. She has released seven studio albums, three live albums, four EPs, and 36 singles before the age of 30!

Her dating life has been just as varied. Openly pansexual, Miley has dated people of all genders over the years, saying that she’s ready to love anyone that loves her for who she is. Her longest relationship was with actor Liam Hemsworth, which lasted for 10 years, although they split in 2019.

Miley’s “teenage dirtbag” phase has, by now, become infamous — mostly due to the fact that Miley literally grew up in front of our very eyes. She went from being Miley, Billy Ray Cyrus’s music-loving kid, to being teen idol Hannah Montana.

With this level of fame, the more Miley broke away from the wholesome Disney Channel star frame and began to explore who she is, the more shrouded in controversy the teen became. Yet, even on her most wild days, she managed to win over her fans.

Jake Gyllenhaal might have had a bit of a leg up in the industry (considering that both of his parents were fairly prominent). But, he has also proven time and again that he’s an extremely gifted and versatile actor in his own right.

He has starred in tons of films including Donnie Darko, Brokeback Mountain, Zodiac, Prince of Persia: The Sands of Time, Spiderman: Far From Home, among many others. As for his personal life, Jake has dated quite a few famous women (Kirsten Dunst, Reese Witherspoon, Taylor Swift), and has been in a relationship with French model Jeanne Cadieu since 2018.

Jake’s first major role as the titular character in Donnie Darko definitely showcased his “emotional teen” vibe. His acting career started long before, thanks to his parents’ connections in the industry.

His parents, though, were the ones who stopped him from breaking out sooner — they allowed him to audition for parts, but regularly forbade him from accepting the roles when he was chosen. Thanks to them, he also worked summer jobs as a lifeguard and as a busboy at a local restaurant.

From teen heartthrob to serious actor, Zac Efron has definitely managed to evolve past his Disney beginnings. Although for a while, it looked like he was only going to be cast in “dude” films (Neighbors, Dirty Grandpa, Mike and Dave Need Wedding Dates), he has found a way to break through into more serious roles.

Unfortunately, the last few years have been quite difficult for the actor. Amidst rumors of plastic surgeries, Zac has recently revealed that he actually shattered his jaw in 2021. He now resides on a secluded property in Australia as he continues to recover and get back into filming.

Despite his jock role in the High School Musical trilogy, Zac actually described himself as a bit of a geek, apparently flipping out if he got a B grade instead of an A. He was also big into musical theater, taking singing lessons and performing in local productions.

As a teen idol, he certainly broke some young hearts when he began his relationship with Vanessa Hudgens in 2007 (although they did split in 2010). While certainly not a teen anymore, he’s still very much loved by young teens and women.

Kristen Stewart has had quite a complicated career. As a young actress, she was often scorned and ridiculed for being expressionless and having the shadow of the Twilight Saga follow her for years. It took a shift from blockbusters to Indie productions for her talent to really shine.

Thanks to her roles in recent years, she’s finally taken seriously for the talent that she is. As for romance, she has been in a very happy relationship with screenwriter Dylan Meyer since 2019 and the two have been engaged since the end of 2021.

As a teen, of course, Kristen was cast in one of the most coveted (and later hated) roles in Hollywood. Winning the role of Bella Swan was definitely life-changing for the young actress as, nearly overnight, she became a massive teen sensation.

The director of the first film in the saga, Chatrine Hardwicke, described teenaged Kristen as “pretty shy and kind of a little bit nervous and awkward.” That was, of course, what made her such a perfect female heroine.

Taylor Swift is probably one of the most successful music artists (female or otherwise) of the past several years. Thanks to her immense talent and incredible performances, she has amassed a very dedicated fan base.

Not only is she an incredible musical talent, but she’s also had a major influence on many young female artists — as well as entire genres of music (like country and pop). A new species of millipede was also named after her!

Taylor wasn’t always the extremely well-regarded artist that she is today. In her early years, many critics considered the young country singer/songwriter a joke — possibly because she was mainly popular with young girls at the time.

She was also often made fun of for writing songs about her exes. But, of course, those stupid criticisms don’t really mean much when you’re one of the biggest acts in the world by the time you’re 20!

Ryan Gosling is definitely one of the suavest and mesmerizing male actors in Hollywood today. Almost effortlessly, he moves from a romantic role to a comedic one; from action films to emotional dramas.

Thanks to his roles in movies like The Notebook, Crazy, Stupid, Love, and La La Land, he’s considered one of the most beloved romantic leads — something that we’re sure his long-time partner Eva Mendes appreciates.

But, Ryan wasn’t always the smooth and confident actor that he is today. As a kid, he was often bullied and struggled with schoolwork. This led to his mother homeschooling him for a year until he felt prepared to return.

His teenage years were spent as a child star, first in the revival of The Mickey Mouse Club and then in several other children’s shows like Goosebumps. He was, however, kicked out of MMC due to apparently having “a big attitude” at age 12.

Leonardo DiCaprio has certainly had quite an impressive career so far. Despite his past as a child star, he’s often cast in serious dramatic and emotional roles. He has shined in movies like The Departed, Shutter Island, Inception, The Great Gatsby, The Wolf of Wall Street, and many more.

As passionate as he is about his career, he’s less so about opening up. Leo rarely agrees to interviews and keeps his personal life fairly private. This, of course, doesn’t stop the media’s wild speculations regarding his romantic relationships.

Leo was certainly one of the biggest teenage heartthrobs back in his youth. He has shared some of the things that pushed him into acting — not only did he hate public school, but he also just preferred auditioning. He also wished to help his family financially.

Thanks to his major roles as a moody teen/suave love interest in the incredibly iconic Romeo+Juliet and Titanic, he became the celebrity crush of nearly every young girl (and a few older ones, too).

Freddie Prinze Jr.’s acting career has been kind of petering out over the last decade. Yet, he’s still undeniably beloved by many of his diehard fans, thanks to both his early work in the ‘90s and his later iconic characters.

He’s especially well-remembered for his portrayal as Fred Jones in the Scooby-Doo movies alongside his wife, Sarah Michelle Gellar. The two don’t just share movie projects, they also have two kids. Freddie is also pretty seriously into Brazilian Jiu-Jitsu.

Freddie has been reported to have shared that his passion for acting was majorly affected in high school. Apparently, Neil Patrick Harris visited the school to get kids excited about acting. Clearly, it worked on Freddie!

His big break, of course, came thanks to his teen blockbusters — I Know What You Did Last Summer (both the first and the second). He became a teen sensation in 1999 with the release of She’s All That, which showed off his romantic potential.

Kylie Jenner is definitely one of the biggest celebs in the world — she’s the most followed woman on Instagram with 455 million followers on the platform (as of 2022) and only second to Cristiano Ronaldo.

She’s also an incredibly successful businesswoman, with her own cosmetics company and several successful fashion lines. Despite the many controversies that she’s been a part of, she’s still an impressive media personality and mother.

Thanks to the widespread fame of Keeping Up With the Kardashians, Kylie very much grew up in front of the cameras — meaning that most of her teen awkward phases were recorded on the show.

It’s also why her lip-fillers became such big news when she turned 18. Several years later, she explained that she got the procedure because a boy commented that she had “such small lips,” which made her insecure.

Chris Even has certainly become one of the biggest blockbuster stars in Hollywood in the past decade, and that success can be directly attributed to his life-changing role as Captain America in the Marvel Cinematic Universe.

Thankfully, he has also done plenty of other movies that showcase his amazing talent and versatility beyond playing the First Avenger. His comedic timing and dramatic flare are especially impressive — just watch Scott Pilgrim vs. the World or Knives Out if you don’t believe us.

Chris is proud of his acting begins, despite them being pretty silly. Not Another Teen Movie was a wild parody that critics hated, but Chris seems to be pretty fine with it. In fact, he thought it was hilarious.

In an interview, he shared, “At the time, I was so thrilled to be a part of the movie, it didn’t even cross my mind that it was some sort of, like, an artistic compromise or something.” It seems that this mindset followed him through the failed Fantastic Four movie, as well.

Paris Hilton has had one of the most interesting celeb careers for the past 20 years. Originally regarded as a ditzy blonde model and socialite, she has since built herself a business empire as a serious entrepreneur.

Not only is she an actor, singer, and published author, but she’s also a social media mogul and a serious boss when it comes to her many business ventures. While she might have once been regarded as “famous for being famous,” she has since proven that she’s a force to be reckoned with.

Long before the Kardashians, Paris hit the celebrity scene with the full force of her “party girl” energy. She was truly the first influencer — setting trends that just about every teen girl at the time followed religiously.

Her “It Girl” status naturally came with plenty of scandals and controversies — including the famous tape that was leaked in 2001, and her trouble with the law throughout the years.

You can’t talk about Aaron Paul without talking about his pivotal role in one of the most influential and beloved shows of the last two decades. All through his big break in HBO’s Big Love, Breaking Bad was the real breakthrough!

He actually got a tattoo with his co-star Bryan Cranston after the final episode of Breaking Bad. The two are still very close — they run a business together and find just about any opportunity to work together!

Aaron was interested in acting from an early age as he got a taste of it during local theater productions. It seems that the rest of school wasn’t very interesting to him because as soon as he graduated he drove with his mom up to LA with all his savings.

While Jesse Pinkman is far from who Aaron is in real life, it seems that the awful teen fashion of the early 2000s “dirtbag” era definitely affected both of them.

Nowadays, it seems that Joe Jonas is mostly occupied with his beautiful family. Joe and his now-wife, Sophie Turner, have been dating since 2016. They tied the knot in 2019 and had their first child in 2020.

They welcomed a second daughter in the summer of 2022. On a professional front, he’s busy with the return of the Jonas Brothers and with a return to his acting career with the movie Devotion.

Joe is well-known for his teen success as part of the Jonas Brothers with two of his brothers, Kevin and Nick. With the success of the teen boy band came Disney Channel appearances.

This led to the brothers starring in the Disney Channel movie Camp Rock alongside Demi Lovato. While it may seem like a cringy film now, there’s no denying the following it had upon its release.

Anyone who has listened to the radio in the past few years could not have missed Ariana Grande’s unique voice. Thanks to her unique style and incredible four-octave vocal range, she has become a force to be reckoned with in 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 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.

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.

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.

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’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!

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.

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 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 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 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.

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.

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’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 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’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.”