Who doesn’t love a great teen flick?

Teen movies and TV shows are what got us through our awkward years, as we saw people portrayed on screen who really embodied our adolescent insecurities. We understood what it was like for McLovin in those harsh high school times. We knew what it was like to care so deeply about your marks that everything else paled in comparison until you ended up fooling around with a teacher. Okay, maybe not. (But somebody does!) Whether you were one of the Mean Girls or Freaks and Geeks, we all have our own cinematic high school counterparts.

But did you know that most of the “teenagers” you grew up watching weren’t really teenagers at all? Many of the actors you remember as your favorite high school bullies and losers had already graduated from college before they played their seminal roles. Many actors get typecast in high school movies and continue acting in them well past the age where they could ever attend a real high school. Some even made whole careers out of remaining forever 17.

Because the actors on this list were young and hot, we bought that they were still just 15 or 17 or whatever. But that’s easy enough for us as a viewer. With their co-stars, though, their real-life ages make for some awkward onscreen situations. Making out with a 15-year-old is fine if you’re character’s only 16, but what if the actor playing him is actually 26? What about having an onscreen mom who’s less than 10 years older than you in real life?

Regina George (Rachel McAdams) In Mean Girls

Who can forget the Queen of the Plastics? In the flick, Regina George leads a posse of preppy girls in their war against the rest of the school, pretending to be nice and perfect to everyone but spreading nasty rumors and slandering everyone in their top-secret “Burn Book.” The Meanest Mean Girl might have been a vindictive high school senior, but Rachel McAdams, who played George, was far from a high school student when she played the role. McAdams was already 26 when Mean Girls came out.

Incredibly, Regina’s mother in the movie is played by Amy Poehler, who is just 7 years older than McAdams in real life. Despite the fact that the role was written for Poehler by her Saturday Night Live co-star, Tina Fey, she almost didn’t get the part because she looked too young to be the mother of a high school student. So if you ever wondered why Regina and her mother looked so similar, there’s your answer.

Donnie Darko (Jake Gyllenhaal) In Donnie Darko

Donnie Darko is a creepy movie about a troubled teenager who is haunted by a gigantic rabbit. The rabbit prophecies the approaching end of the world, and the movie leaves us to question whether the young main character is schizophrenic or suicidal or whether the world is really ending. While it was critically acclaimed when it came out back in 2001, it’s a very weird movie and hard to understand on the first watch. It's very open to interpretation and needs to be watched a few times to really get it.

But while Donnie in the movie is still in high school and that might help explain his troubled mind (well, depending on what you believe about the movie), Gyllenhaal was actually 21 when the movie came out. I guess it would have been hard for a character who was actually seventeen to accurately portray such a complex, confusing, and dark role.

Sabrina Spellman (Melissa Joan Hart) In Sabrina, The Teenage Witch

It turns out that everybody’s favorite teenage witch was playing a hex on us all along.

Melissa Joan Hart played Sabrina, a high schooler who appeared to the rest of the world to be living with two normal aunts and a black cat. But really, as all viewers of the show knew, Salem was a talking cat, her aunts were really ancient witches, and Sabrina was a witch in training.

Sabrina’s magic occasionally got her into sticky situations around her high school as she accidentally made something happen without thinking through the consequences first—like a flighty high school girl totally would if she had magical powers. The show was funny and silly and really just a big metaphor about how life kinda sucks when you’re growing up.

But while Sabrina: The Teenage Witch was a kids’ show about teenagers, Melissa Joan Hart was 20 before she first appeared as a teenage witch in Season 1 and continued playing the teenager for seven more years.

Dorothy Gale (Judy Garland) In The Wizard Of Oz

The Wizard of Oz is an iconic fantasy film about an innocent young girl who gets caught up in a twister and winds up tasked with saving a magical land from evil witches.

Judy Garland doesn’t quite belong on this list–she was 16 when she played the part of Dorothy–but in this case, rather than an adult playing a teen, she was a teen who was playing a child. The character of Dorothy Gale is only supposed to be twelve years old. Since Garland had hit puberty before taking on the role, the costume designers outfitted her in a gingham dress that hid her features and made her look more like the small child that the role demanded. She was under 5 feet tall, which helped add to the illusion when she stood next to the taller actors who played the Tin Man and The Cowardly Lion.

In the end, The Wizard of Oz was probably the biggest success of Garland’s career despite the fact that she was playing a part she was 5 years too old for.

Steven Hyde (Danny Masterson) In That ‘70s Show

Who can forget the too-cool-for-school stoner from That 70’s Show? Well, it turns out that Danny Masterson really was too cool for school—he was several years older than the rest of his co-stars hanging out in Eric Forman’s basement. He was originally considered too old for the part but won over the casting director at his audition and took on the legendary role of Hyde anyway. Masterson was 22 at the outset of Season 1 and turning thirty by the time the Point Place kids finally went off the air in 2006. In the show, his excessive maturity is explained away by the fact that he’s had a tough childhood with no father and an absentee mother and has basically learned how to get by on his own by high school.

It’s a good thing that his onscreen romance with Jackie didn’t start until Season 5—Mila Kunis lied about her age to get the job at just 14 years of age and was underage for the first three seasons of the show. As it was, they dated when the real-life Jackie was 19 and the real-life Hyde was 27. Still gross, but legal.

Tracy Flick (Reese Witherspoon) In Election

Ah, Election. That fun little movie about a psycho high school girl who sleeps with her teachers and just has to win her student council election. While the subject matter of the film is a little creepy (and statutory), at least Witherspoon wasn’t actually a high school student while filming the role. She was already 23 years old when the film came out in 1999.

The film itself features all sorts of racy high school antics which couldn’t have been shown if the stars had actually been of high school age. Flick thinks that her teacher can’t resist her youthful attractiveness and tries to manipulate him, which causes him to be dragged into all sorts of manipulation in order to prevent her winning the student body election. Flick’s competitors in the school election, siblings Tammy and Paul Metzler, were portrayed by 17-year-old Jessica Campbell and 20-year-old Chris Klein. Both characters slept with the same girl named Lisa in the movie, and Klein, in particular, has a fairly graphically suggestive scene with her.

Maya St Germain (Bianca Lawson) In Pretty Little Liars

Pretty Little Liars is a show about a typical upper-class clique of preppy teenage girls who find themselves caught up in a murder plot after one of them goes missing. It’s a very high school type of show, and the characters begin Season 1 of the show at about 16 years of age. With the exception of Sasha Pieterse, who plays the missing Alison in flashbacks, most of the actresses portraying the Liars are a few years older than their character. But no one takes the cake for being too old for her role like Bianca Lawson, who plays Maya St Germain. Maya is a new girl who comes to the school and starts a lesbian relationship with one of the Liars named Emily. Bianca Lawson was 31 when she took on the role and 33 by the time she left the show after Season 3.

Incredibly, Bianca also portrayed teenager Megan Jones on Saved By The Bell, which went on the air way back in 1993. So she’s basically been a teenager for twenty years running…

Andy (Paul Rudd) In Wet Hot American Summer

Wet Hot American Summer is about a bunch of teenagers working as camp counselors and all the crazy antics they get up to on the last day of summer. Andy is the super hunky but douchey boyfriend of the gorgeous Katie (Marguerite Moreau) but can’t keep his lips off of Lindsay (Elizabeth Banks). While most of the actors in the movie were well past their high school days by the time it was filmed, Rudd stands out because he was already in his 30’s when he played this immature slacker.

The prequel to the movie, the Netflix miniseries Wet Hot American Summer: First Day of Camp, puts a spin on this whole list by taking the same actors 15 years later and putting them right back into the same teenage roles they played in 2001. Instead of a bunch of 20-somethings acting like they were still in high school, it features a bunch of 40-somethings pretending they’re still in high school. It’s ridiculous, but somehow it works (sort of).

Jim Levenstein (Jason Biggs) In American Pie

American Pie is a legendary high school film. Jim is a virgin who is about to graduate high school and desperately needs to rectify his situation by prom. But while Biggs plays the most awkward of the four bros in the friend group who vow to get laid together, did you know that Jason Biggs was actually 21–and older than the actors playing Paul Finch, Kevin Myers, and Oz–when the movie came out? Jim bumbles his way through the movie, constantly being the object of others’ derision with his pathetic attempts to get it on whether it’s with Nadia or the titular pie.

Notably, Chris Klein manages to show up twice in a row on this list, for two different movies that came out in the same year. He was 20 in 1999, yet played the virginal lacrosse player here and the nice-guy football player who almost wins the election in Election. Guy sure knew how to make a career out of playing a high school jock.

Xander Harris (Nicholas Brendan) In Buffy: The Vampire Slayer

Buffy is a high school girl in California who’s just trying to lead a normal life but can’t help but save the world from vampires. But while her vampire-fighting team may have started out as teenagers in high school on the show, they were much older in real life. While Sarah Michelle Gellar was already 20 by the time she appeared in season 1, Willow (Alyson Hannigan) was 23 and Xander (Nicholas Brendan) was actually 26! Those are some old sophomores…

The characters graduated from Sunnydale High in Season 3, which means that Xander was almost 30 years old by the time he went to prom. I know with all the vampires and demons flying around and questions of eternal life and undeadness, age might not have seemed that important, but I don’t know a lot of high schools that would let a 28-year-old show up for prom…

Zach Gilford (Matt Saracen) In Friday Night Lights

Most Friday Night Lights fans will remember Matt Saracen as Jason Street’s understated understudy–the backup quarterback who would never play–who was thrust into a starting role after Jason Street’s horrific injury. Over his high school career, Saracen becomes a focal point of the team and the show. But while Matt was a sophomore in high school at the outset of the series, Zach Gilford–the actor who plays him–was actually 24 by the time the series started. Aimee Teagarden, who plays Julie, Saracen’s love interest portrayed as being one year behind him, was actually seven years younger in real life. Gilford was 24 and Teagarden was 17 when they hooked up on the show.

Several other high school football stars in the show were older than the characters they portrayed as well. Tim Riggins (Taylor Kitch) and Jason Street (Scott Porter) were 25 and 27, respectively, in Season One.

Chastity Church (Gabrielle Union) In 10 Things I Hate About You

10 Things I Hate About You is known for being a typical high school comedy and the launching pad for the career of several future stars (notably Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt). It’s also known for being a modern adaptation of a very old story—The Taming of The Shrew, by a fellow you may have heard of who went by the name of William Shakespeare. Basically, it’s about a guy (Cameron, portrayed by Gordon-Levitt) who wants to date a girl, but things are complicated. Another guy named Joey is also trying to date her but is getting cock-blocked by her single older sister Kat (Julia Stiles). Matchmaking ensues to try and get everyone on the same page, and after a whole bunch of shenanigans, everyone ends up happy...because it’s a Shakespeare comedy.

While the three stars were slightly past high school age at the time the film was made, the banner for “oldest teenager” goes to Gabrielle Union. Union plays Bianca’s best friend, Chastity Church, who winds up dating Joey after Bianca rebuffs him. Union was 27 and a good five years older than the rest of the cast when she played the role.

John Bender (Judd Nelson) In The Breakfast Club

The Breakfast Club is a classic teen film about a group of high school students and the crazy antics they get up to when brought in for detention on a Saturday. While all five students in detention belong to different social cliques during a normal school day, being locked in a room with one another brings them together and allows them to see each other’s perspectives and become friendly at least for the day.

While Anthony Michael Hall and Molly Ringwald were 17 when the film came out, Ally Sheedy and Emilio Estevez were already 23. But Judd Nelson takes the cake as the angry social outcast Bender—Nelson was 26 years old when he played this high schooler. When the romance emerges between Bender and Claire (Ringwald) at the end of the flick, almost a decade separates the two actors.

While Bender does come across as older than the rest of the cast with his who-cares attitude, his character was still supposed to be just seventeen.

Conrad (Timothy Hutton) In Ordinary People

Ordinary People is a dark serious film that came out in 1980 about a suicidal teenager who is dealing with the death of his brother, for which he feels partly responsible. It’s a study on how people relate to one another after a tragedy and whether a family can be brought together again after being torn apart. Based on an award-winning novel with the same title published by Judith Guest in 1976, it’s basically a story about a mother’s isolation from her adolescent son and his confused and grieving father and the barriers between them that just won’t go away.

While the protagonist of the film is a teenager who is struggling with depression and emotional instability, actor Timothy Hutton was actually already 20 by the time the film came out in 1980. He won a Best Supporting Oscar for the role, so I guess it was a good decision. It would have been hard for a real teenager to wrap his head around the rawness of the role.

Dionne (Stacey Dash) In Clueless

Like 10 Things I Hate About You, Clueless is a modern interpretation of an old story re-set in a 1990’s high school. It’s about a rich ditzy high school girl named Cher who ends up coming to terms with the fact that being vapid and rich are not all there is to life. Cher becomes a better person and eventually falls for her stepbrother, played by Paul Rudd (who appears elsewhere on this list). It’s loosely based on the early 19^th century novel Emma by Jane Austen.

Alicia Silverstone was 19 when she played the role, but Cher’s best friend in the film, Dionne, is played by Stacey Dash. Dash was almost 30 when she played the high schooler and had appeared as a teenager a decade previously on The Cosby Show. It’s a reminder that while Clueless was a fun bubblegum version of a high school flick, it wasn’t exactly realistic.