G-Rated Icons Who Took A Chance And Tackled R-Rated Characters
So many actors throughout history have known what it's like to be typecast. Although they may have the skills for a range of different characters, some actors like Seth Rogen or Michelle Rodriquez can find themselves playing similar characters from project to project.
But while that pigeonholing can be frustrating for actors at the best of times, breaking away from it is a particularly risky move if they're only known for light, innocent fare. But that didn't stop some adventurous actors from taking the plunge.
Leonardo DiCaprio - This Boy's Life

Although Leonardo DiCaprio is known as an actor who's unafraid to drive himself to any emotional depth and explore a wide array of characters, that reputation would have been much harder to build without a little movie called This Boy's Life.
Until DiCaprio proved he could hold his own against Robert De Niro in a role that saw the acting legend play his cruel stepfather, he was only known for co-starring in Growing Pains. But This Boy's Life proved he could handle more serious material.
Emma Watson - The Bling Ring

Although Hermione Granger wasn't the only character Emma Watson had played by the time she signed on for The Bling Ring, the fact that it was her first edgy and unsympathetic character meant she had to fight for the role.
As the Harry Potter actress told British GQ, "I'm probably the least obvious choice to play the role, as she's the epitome of everything that I am considered not to be."
Matthew McConaughey - Dallas Buyers Club

Throughout the 2000s, Matthew McConaughey earned himself a reputation for being the funny good-looking guy next door in films such as How to Lose a Guy in 10 Days and Fools Gold. That being said, he quickly kicked that typecasting aside when he dove into the role of Ron Woodroof in the R-rated drama Dallas Buyers Club.
Showing off his range and commitment to such a challenging role, McConaughey walked away with an Academy Award for Best Actor.
Selena Gomez - Spring Breakers

Although she's more known for her successful music career, Selena Gomez first came to prominence through Disney productions like Wizards of Waverly Place.
And while even Gomez's current roles don't tend to venture into particularly edgy territory, it was clear that the former Disney star didn't want her squeaky-clean image to define her by the 2010s. Because 2012 would see her star in the vulgar and polarizing Harmony Korine film Spring Breakers.
Reese Witherspoon - Freeway

Although Reese Witherspoon has long appeared in movies that dealt with more serious subject matter than perky, ebullient reputation would suggest, her characters in American Psycho or Cruel Intentions didn't stray far from that archetype.
However, it turns out Witherspoon has been playing against typecasting before she even had one. After all, she played a gun-toting delinquent opposite Kiefer Sutherland's disturbing turn as a deranged criminal in 1996's Freeway.
Tom Hanks - Road To Perdition

Throughout the '90s, Tom Hanks branched out from the light fare that made him a big star in the '80s with challenging projects like Cast Away, The Green Mile, and Saving Private Ryan.
But while those movies had overall darker tones than his previous work, Hanks nonetheless played noble and heroic characters in them. The same could not be said for Road To Perdition from 2002, where Hanks stars as a mob hitman who is only made even anti-heroic by personal circumstances.
Jennifer Aniston - Leprechaun

Sometimes an unusual role can come as an experiment for an actor who's already established their fame. But Jennifer Aniston's first big outlier came when she was still making her way through the industry and taking what she could get.
So while audiences mostly know Aniston for romantic comedies thanks to Friends, it was only a year before she started to work on that show that she played an action heroine in the bizarre horror-comedy Leprechaun.
Jim Carrey - The Cable Guy

Although Jim Carrey excelled in movies that blended his dramatic talents with his comedic stylings, like in Dumb and Dumber and Ace Ventura, his first big departure from his trademark zaniness was his dark turn in The Cable Guy.
Although it was maligned in 1996 and remains polarizing decades later, Carrey's sinister role in this black comedy hinted at the depths of his capabilities.
Anne Hathaway - Rachel Getting Married

Anne Hathaway made herself one of America's prime sweethearts with the purely innocent The Princess Diaries series.
But while that made her an important part of so many people's childhoods, that squeaky-clean box can be pretty restrictive for an artist. That's likely what drew her to the complicated recovering addict Kym in the independent drama Rachel Getting Married, which secured her an Oscar nomination.
Robin Williams - One Hour Photo

Those who had seen Robin Williams's stand-up act by 2002 knew his sense of humor wasn't always G-rated. And through movies like Good Will Hunting and Awakenings, he proved his acting talents could extend far beyond strictly comedic roles.
Still, he had nonetheless cemented his image as a family-friendly funnyman through movies like Mrs. Doubtfire enough that it came as a shock to audiences to see him play disturbed, villainous characters in Insomnia and One Hour Photo. But to his credit, Williams played those roles chillingly well too.
Steve Carell - Foxcatcher

Although it would be a stretch to call Steve Carell's comedic characters "G-rated," he often imbued them with a goofy childishness that ultimately made them seem harmless.
Naturally, this made it all the more intriguing when he seemingly purged his charisma to play the deeply unsettling John du Pont in the historical wrestling drama, Foxcatcher.
John Goodman - O Brother, Where Art Thou?

With decades in Hollywood under his belt, John Goodman has played a wide range of compelling characters. But while his early stand-out roles, like Dan Conner in Roseanne and Walter Sobchak in The Big Lebowski, were rough around the edges, they were ultimately pretty lovable.
But in O Brother, Where Art Thou?, viewers were formally introduced to his dark side in the form of Big Dan Teague, a superficially charming salesman concealing his purely evil nature.
Gregory Peck - The Boys From Brazil

Atticus Finch from To Kill The Mockingbird goes down as one of the most honorable and dignified characters in the history of fiction, and he wasn't far off from the sorts of people Gregory Peck typically found himself portraying.
But while Peck played a few villainous roles throughout his career, none were more infamous than war criminal Dr. Josef Mengele, who Peck portrayed in The Boys From Brazil.
Adam Sandler - Punch Drunk Love

At best, people could typically refer to Adam Sandler's output in the '90s as "PG-13" rather than "G-rated," but he didn't fully cross into R-rated territory until the gripping Punch Drunk Love.
While his previous characters could be violent and immature, these traits were largely played for comedy before. But with Punch Drunk Love's Barry Egan, those traits become disturbing and compelling all at once.
Zac Efron - The Paperboy

While Zac Efron is hardly any stranger to raunchy comedies, he had a long road to get there from fare like 17 Again and the High School Musical series that made him a household name among tweens at the time.
And that transition seemed to begin with 2012's The Paperboy, a thriller that saw Efron drive for a detective — played by Matthew McConaughey — while entering a complex romantic relationship with a criminal's fiance, played by Nicole Kidman. After that, audiences didn't find it hard to take Efron seriously as an adult.
Brad Pitt - Kalifornia

Although Brad Pitt's handsome looks have long come secondary to his impressive range as an actor, that wasn't always the case for the Hollywood megastar.
J.D. in Thelma and Louise serves as a perfect example of the charming pretty boys Pitt was once limited to, but his portrayal of an unkempt serial killer in Kalifornia was his first major step out of that typecasting.
Zendaya - Euphoria

For many years, Zendaya had gracefully transitioned from Disney child star to bankable actress with key roles in the Tom Holland Spider-Man movies and The Greatest Showman.
But while some former child stars tend to jump right into riskier roles like Zendaya's starring turn as Rue Bennett in Euphoria, she waited before her career was more established before adding a troubled teen to her acting repertoire.
Vanessa Hudgens - Spring Breakers

Like her fellow Disney alumnus Selena Gomez, High School Musical star Vanessa Hudgens was in the midst of branching out from her family-friendly roots as the 2000s ended. But while her turns in Rent and Sucker Punch were steps toward more adult fare, Spring Breakers was likely her most high-profile case of playing against type.
And at first, that jump to Spring Breakers was as jarring to see for her as for her fans. As Hudgens told Vanity Fair, "I think just the first time watching it, I was in a state of shock through the entire thing."
Dianna Agron - Bare

Although Dianna Agron secured a plumb role as Quinn Fabray in Glee, an ultimately campy show loaded with silly musical numbers tends to shape an actor's career in a way that can feel hard to break away from.
And while it wasn't in a particularly well-known movie, that's likely what Agron set out to do when she accepted the role of an exotic dancer who dabbles in illicit substances in Bare.
George Clooney - From Dusk Till Dawn

By the time George Clooney signed on to Quentin Tarantino's From Dusk Till Dawn, he was chiefly known as a heart-throb doctor in the long-running hospital drama E.R.
But while his character Seth is easily the more reasonable of the law-breaking Gecko brothers, that doesn't make him any less of a ruthless criminal. Once that movie succeeded, it became clear just how capable of an actor Clooney really is.
Jennifer Lopez - My Family

Curiously, Jennifer Lopez's first role in an R-rated movie came not only before more crowd-pleasing fare like Maid In Manhattan but even before she cut her first album.
The 1995 movie My Family saw her play a first-generation mother who faces deportation after emigrating from Mexico. As this is a movie that spans decades, she plays the younger version of that character.
Elijah Wood - Sin City

Thanks in large part to his boyish looks, Elijah Wood has often played innocent, kind characters even after he was no longer a child actor.
However, one of his most memorable roles is the silent and eerily calm serial killer who does unspeakable things to his victims in Sin City.
Alexa PanVega - Machete Kills

It's not uncommon for a director to develop a stable of actors they enjoy working with, and Robert Rodiguez can definitely be considered one of them.
So while it's common for child stars to gravitate toward more risqué material when they grow up, it seemed like a particularly natural progression for Alexa PanVega to appear in one of Rodriquez's adult-oriented movies, namely Machete Kills, after a near lifetime of working with him on the Spy Kids series.
Henry Fonda - Once Upon A Time In The West

Not only was Henry Fonda's role as the truly monstrous Frank in Once Upon A Time In The West a vast departure from his heroic roles in films like 12 Angry Men, but that was precisely why Sergio Leone wanted him in the part.
Fonda broke away from his righteous, good-guy stereotype to play a hardcore man in the wild west. According to Leone, the chance to work alongside Fonda was the reason why he agreed to make another western film.
Drew Barrymore - Poison Ivy

Although Drew Barrymore grew up sadly fast in Hollywood, as far as anyone knew at the time, she was just known as the innocent little star of E.T. by the time she starred in Poison Ivy.
This movie was a provocative thriller full of racy intrigue, and Barrymore's character Ivy was a big part of why.
Jeff Bridges - Jagged Edge

Although Jeff Bridges is no stranger to R-rated movies, they receive that rating due to the language in them, as he often comes across as a nice, likable person.
However, he turns out to be much more sinister in the movie Jagged Edge, which certainly makes his character's legal predicament more complicated.