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.
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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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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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.
Keiko Agena
[ranking: 15]
Role: Lane Kim in Gilmore GirlsCharacter Age: 16 and upReal Age: 27-34
Keiko Agena was 27 when she started playing a 16-year-old on Gilmore Girls, and she probably could have passed for 14. At no point in her seven years of aging during the show did she look too old for the part. A rare time when casting an older actor worked out wonderfully.
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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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