Stockard Channing
[ranking: 1]
Role: Rizzo in GreaseCharacter Age: 17Real Age: 33
Yes, in perhaps the most extreme case, Stockard Channing played a character half her actual age. If you really take the time to look at her, you can see it, but given the era the film takes place in she actually gets away with it, portraying the world-weary and street-wise Rizzo. John Travolta is distracting enough to help, too.
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Henry Winkler
[ranking: 2]
Role: Fonzie in Happy DaysCharacter Age: 18ishReal Age: 28
Henry Winkler was 28 when he was cast as Arthur Fonzarelli, meaning he was 35 when the show finally came to an end, and he was still playing the young rebel. Did he fool anyone? Not really. But he was the Fonz, a character oozing cool, so did anyone even care?
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Gabrielle Carteris
[ranking: 3]
Role: Andrea Zuckerman in Beverly Hills, 90210Character Age: 16Real Age: 29
The cast of 90210 are perennial youths and the same is true for Gabrielle Carteris. Even though she was 13-years-older than her character, the audience was none-the-wiser. Though, she pulled off the character's age, her unfortunate wardrobe gave her a bit of a reputation as the "mom" of the 90210 teen crowd.
Tobey Maguire
[ranking: 4]
Role: Peter Parker in the Spider-Man trilogyCharacter Age: 17-18Real Age: 27-32
It's never explicitly stated how old Peter Parker is, but in the first movie he is in high school, so he's likely 17 or 18. Tobey Maguire, as baby-faced as he is at 27, doesn't quite pull it off. Peter Parker, somehow, looks simultaneously 12 and 45. Tobey can do nerd just fine, but teenager... not so much.
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Tom Welling
[ranking: 5]
Role: Clark Kent in SmallvilleCharacter Age: 14 and upReal Age: 24
Sure, Tom Welling was only 24 when he started playing a young Superman - not bad for Hollywood - but did he look like a 14-year-old? No. As Clark aged, so did Tom, and he never really looked like a high school student. To be fair, this can be explained away by Superman's inherent superiority.
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Charisma Carpenter
[ranking: 6]
Role: Cordelia Chase in Buffy the Vampire SlayerCharacter Age: 17Real Age: 27-32
Charisma Carpenter played your typical mean girl in Buffy. And a mean girl is usually depicted as quite attractive. So while Carpenter's casting is reasonable, she very much looks 27 when side by side with actors who were so much younger.
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Michael J. Fox
[ranking: 7]
Role: Marty McFly in Back to the Future Part IIICharacter Age: 17Real Age: 29
Though Michael J. Fox is famously baby-faced, he couldn't keep up the 17-year-old charade forever. Sure, he was believable as a high schooler in the first Back to the Future, but by the time he started traveling back to the Wild West at the same age, he sure wasn't getting rejected at the saloon.
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Jason Earles
[ranking: 8]
Role: Jackson Stewart in Hannah MontanaCharacter Age: 16-18Real Age: 29-34
Jason Earles is the Gary Coleman of mid-2000s Disney Channel sitcoms. Though he was already 29 when he started playing Miley Cyrus's high school aged brother, he could have been convincing as a middle-schooler, and probably still could have when filming wrapped five years later.
Shirley Henderson
[ranking: 9]
Role: Moaning Myrtle in the Harry Potter seriesCharacter Age: 16Real Age: 37-40
When Shirley Henderson first played Moaning Myrtle in 2002's Harry Potter and the Chamber of Secrets, she was already 37. Three years later she reprised the role in Goblet of Fire, by which time she was 40. Amazingly, however, she pulled it off. Her ghostly opacity probably helped, not to mention her high pitched young-girl voice.
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Alan Ruck
[ranking: 10]
Role: Cameron Frye in Ferris Bueller's Day OffCharacter Age: 18Real Age: 30
Not only did Alan Ruck look like a teenager when he was 30, he did a damn good job of portraying one, too. Angsty and whiny, it's nigh impossible to tell that Ruck was actually 12 years out of high school.
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Stacey Dash
[ranking: 11]
Role: Dionne in CluelessCharacter Age: 17Real Age: 28
Stacey Dash was almost 30 when she played best friend to Cher (Alicia Silverstone) in Clueless. Which means to recall what it was like to be a high schooler, she'd need to remember back to the '80s. Considering how definitively '90s Clueless is, it's amazing no one questioned her performance much at all.
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Cory Monteith
[ranking: 12]
Role: Finn Hudson in GleeCharacter Age: 16-19Real Age: 27-31
Supposedly Ryan Murphy made it so the characters on Glee graduated in a realistic timeframe on the show simply because Cory Monteith was aging so much faster than the rest of the actors. Whether that's true or not, no one questioned it. Sadly, viewers didn't get to see what Finn looked like into adulthood before Monteith's untimely death made his age a moot point.
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Rachel McAdams
[ranking: 13]
Role: Regina George in Mean GirlsCharacter Age: 16Real Age: 25
It's hard to imagine anyone else playing the singularly evil teen queen, Regina George, so clearly no one has batted an eyelash at Rachel McAdams's performance. She may have been almost a decade older than her character, but she's still the best casting choice they could have made.
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Andrew Garfield
[ranking: 14]
Role: Peter Parker in The Amazing Spider-Man duologyCharacter Age: 17-18Real Age: 28
Though Garfield was perhaps a little closer in age to Parker than Maguire was when he played him, both pale in comparison to Tom Holland who actually was a teenager when he filmed his first Spidey scene. The lack of enthusiasm around Garfield as Parker has less to do with him pulling off Parker's age and more that the films weren't particularly written well. Garfield could be a teen but he just couldn't be a nerdy superhero teen to satisfaction.
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