
Of course, let’s be honest: if you’re like most people, if you’ve seen a “High School-orchid-hued” show, looked, and said, “That is so not a 16-year-old,” you were probably right. It seems a long-time Hollywood career has included playing teens so old, so grown, that they could almost pass as teachers/specimen politicians. Some of these scenarios pass reasonably well, some are laughably bad, while others simply baffle teens. Here is a list of 10 funniest moments when adults played teens, and what these weird casting decisions truly demonstrate beyond simply something unusual behind the cameras.

10. Jason Earles – Hannah Montana
With the entrance on Disney Channel of Hannah Montana, Jason Earles, playing Jackson, Miley’s fun-loving older brother, himself was close to being 30, yet managed to convincingly act opposite teen-stars who were really teens for many years, partly because of the shock of many of those young viewers—and subsequently becoming an inside joke on Hannah Montana—that Jason was over a decade older than his on-screen role.

9. Bianca Lawson – Pretty Little Liars
Bianca Lawson appears to have made a career out of playing teenage characters well after her own teenage years were behind her. Taking on the role of Maya St. Germain in Pretty Little Liars at the ripe old age of 31, Lawson was by no means a stranger to the halls of a television high school. She had already appeared in a number of television programs, including Buffy the Vampire Slayer and Teen Wolf, both of which feature teenage characters. Lawson’s preternaturally youthful appearance makes her the go-to teen actress, regardless of the era.

8. Stockard Channing – Grease
Okay, sure, Grease is a classic—but come on, the cast seemed more like they’d attend a PTA meeting rather than study hall. Stockard Channing was 33 when she portrayed Rizzo, the tough-as-nails leader of the Pink Ladies. She certainly seemed to have more “cool aunt” energy than “classmate,” but her acting was unforgettable and solidified her character as a timeless classic.

7. Alan Ruck – Ferris Bueller’s Day Off
Cameron Frye was slated to be a senior in high school. Alan Ruck? He was 29. Sure, his youthfulness allowed him to fit in then, but once you know, you can’t unknow—particularly when you know he was more on par with age-wise the actors who played the parents than he was with Matthew Broderick as Ferris.

6. Andrew Garfield – The Amazing Spider-Man
Peter Parker was scripted as an uncomfortable high school teenager, but when Andrew Garfield swung onto screen, he was already 27. His sincere performance rang true, but the age difference caught up to him, particularly in those “teen angst” scenes that seemed a tad too refined on the lips of someone close to 30.

5. Alexa Demie – Euphoria
Euphoria is renowned for depicting high school life with gritty intensity—but in real life, several of its stars are actually way beyond their high school years. Alexa Demie, who portrays Maddy Perez, was 29 when season one rolled around and is currently in her 30s, still acting like a teenager. No surprise the show’s high school corridors resemble more of a catwalk than a sophomore homeroom.

4. Darren Barnet – Never Have I Ever
Paxton Hall-Yoshida is Never Have I Ever’s teen heartthrob fantasy boy—but Darren Barnet was 30 when he played him. Though plenty of his castmates are older than their characters, too, Barnet’s adult features made the disparity particularly obvious. It was like watching someone’s grad-school crush stroll into algebra class when you saw him play 16.

3. Shirley Henderson – Harry Potter and the Chamber of Secrets
Moaning Myrtle is a 14-year-old ghost who is cursed to haunt Hogwarts’ bathrooms eternally. Shirley Henderson was not actually 14, however—she was 37 when she acted the part. To her credit, her performance was so perfect that most audiences didn’t even notice the enormous age gap—until they checked on it later and were shocked.

2. Stacey Dash – Clueless
Dionne Davenport is high school cool incarnate in Clueless, but Stacey Dash was 28 when the film came out. A full ten years older than her character, Dash performed the role with humor and panache, but her casting demonstrates precisely how Hollywood’s conception of “teenager” tends to carry a driver’s license, a credit card, and a few years’ worth of life experience.

1. Barbra Streisand – Yentl
And the crown is awarded to Barbra Streisand. In Yentl, she played a 17-year-old pupil while being 41 in real life. It’s one of the widest age discrepancies ever in Hollywood casting. Streisand gave an incredible performance, but the fact of a 40-something-year-old playing a teenager is impossible not to double-take at.

Some of that has to do with logistics. Actual teenagers are more difficult to cast because of labor laws, school obligations, and levels of maturity, particularly for projects involving intense or adult themes. But there is a downside: casting adults as teens distorts the way real teenagers perceive themselves. When the “typical” teenager on television appears to have just walked out of a photo shoot—acne-free skin, chiseled jawlines, and the confidence of someone who has already made it through their twenties—it creates unrealistic expectations.

Clinical psychologist Dr. Barbara Greenberg explains that this can send negative messages: actual teenagers may feel they ought to appear older, be more grown-up, or measure up to an idealized form of adolescence. Include programs where “teens” are always at crazy parties or in complicated relationships, and actual teens feel left behind. The net result? A generation of children coerced into meeting the glossy, unreal Hollywood ideal of teen life. Perhaps the time has come for a twist of plot—where teenagers on screen are, finally, acted by teenagers themselves.