Admit it: You probably have a favorite teen flick featuring a parade of high school stereotypes, an oddball person for a protagonist, and an unlikely romance to boot. Bet it’s also a comedy! So that’s exactly what The Duff is. Released in 2015, The Duff tells the tale of a senior high schooler named Bianca. She has two pretty best friends, Casey and Jess. All seems cool in her universe, until his jock neighbor Wesley introduces a weird concept to her: that Bianca is a DUFF, or the Designated Ugly Fat Friend.
Soon, Bianca surveys her school and notices that each “social class” indeed has a duff. But she refuses to be one, so she distances herself from her two friends. She also goes into an exchange deal with Wesley to turn her into a non-duff as she tutors him in chemistry.
Every generation seems to have a term for such social outcasts in high school set-ups. If the 2010s have their duff, earlier generations also had their own personas like The Duff, but maybe not as overtly called as such. Take a look at our list of classic movies like The Duff and you’ll get what we’re talking about.
1. Heathers
The 1988 film Heathers is the first in our list of movies like The Duff, primarily because of its subject matter and comedy vibe. However, the comedy it provides us is a darker one, but its topics are as brave as our 2015 film favorite.
Heathers stars Winona Ryder, a popular high school girl named Veronica who’s also friends with three other popular girls termed as “The Heathers.” That’s because these three other girls are all named Heather. But unlike Veronica, the Heathers are rather vicious vixens, so of course their school hates them.
As Veronica gets tired of the Heathers’ company, enter a new outlier of the social cliques named JD. This guy has some sort of darkness in him, which intrigues Veronica. They soon date and sort of become a couple. At the same time, there seems to be a friend fallout between Veronica and some of the Heathers. This eventually figures into the battle of the high school cliques.
Just how dark is JD? Well, it starts with humoring Veronica’s “think out loud” nasty thoughts – thoughts that JD turns into actions himself. It starts with Veronica thinking that one of the Heathers should be given some chemical to drink to make her puke. JD ends up giving the Heather girl a chemical alright, but it kills her! Yes, the film gets a bit dark in its comedy.
What’s a high school film without the stereotypes fighting with each other? Well, this is what Veronica encounters as well, as some of the Heathers try to destroy her reputation, with the help of some jocks. All hell really breaks loose in here, that’s why it’s better if you watch if and find out what happens next!
2. Grease
Grease might be the oldest film in our list here, but this 1978 classic is a musical! So that alone transcends time – and storylines.
The film features an Australian newbie in an American hood, Sandy. She’s not as cool as the ruling rebels of her new high school. But apparently, she had a summer fling with one of those male rebels, Danny Zuko. But come school time, Danny distances himself from the geeky Sandy, not wanting to tarnish his cool bad boy image and reputation. Of course, this crushes goody two-shoes Sandy to no end.
In this film, we can see how high school stereotypes have existed in Hollywood’s depiction of teenagers. While this 1970s film is set in the 1950s, it’s evident that such high school social structures have been existing long before The Duff presented it. And their depictions are also hilarious here. Imagine the greasy-haired boy Danny trying out to become a jock! Those sequences alone are enough for you to consider this movie musical as one of those quirky movies like The Duff.
Like The Duff, Grease presents an unlikely couple in the form of Sandy and Danny. They are presented as poles apart when they meet again in school. But during the summertime, they seem to be peas in a pod. But Danny’s male ego gets in the way of showing his true emotions to Sandy. Bah, pride!
And as with Bianca in The Duff, our heroine Sandy also tries her hand at adapting to certain changes to fit it. But will it work or not? Well, try to watch Grease and find out – and sing along with them, for fun!
3. Some Kind of Wonderful
A classic 1987 film that clearly belongs to this list of movies like The Duff is Some Kind of Wonderful, written by the king of ‘80s teen films, John Hughes. This film is one of his most successful creations, since its story remains timeless.
While it’s not exactly a comedy, this teen drama also provides some heartfelt humor every now and then. We follow the story of Keith, a high school student who also works as a mechanic, just like his blue-collar father. They kinda have some tension about Keith’s future, as his father urges him to save up for a college education.
Keith has a best friend named Watts, a spunky girl who appears tomboyish to everyone in school. The two are very close, as they are also in the lower rungs of their high school’s social circles. Like Keith, Watts comes from a not-so-affluent family. And this social status of their families also affects their social status in school.
Now why would high school students look at class standings so closely? That’s because the richer boys and girls are always the ones ending up together. Of course, it poses some trouble whenever someone from the lower classes aspires to be with someone from the higher classes.
But guess what: our underdog hero Keith, as blue-collar as he is, harbors a huge crush on rich girl Amanda Jones. He even tries to get a date with her. And he solicits the help and assistance of best friend Watts to pull off this date with Amanda. Of course, as an added spice, clueless Keith doesn’t know that his best friend Watts is actually in love with him.
What a dilemma, huh? Go watch this classic and find out what happens to them!
4. Clueless
Every kid or teen who grew up in the ‘90s is sure to mention Clueless. Set in a posh high school, we follow the story of Cher who’s not really such an underdog here. But like in The Duff, she is surrounded by various high school stereotypes, and she also has her own social clique.
The very funny Alicia Silverstone headlines this film. Imagine her saying “As if!” That line became like a motto of every high schooler of the time. People say that expression whenever they’re surprised or if they find something ridiculous. And that expression is now an immortal part of Hollywood history.
Unlike The Duff, though, our heroine Cher is a top dog in this high school pack, so to speak. She’s a rich spoiled brat, but her heart is also in the right place – sometimes. She identifies people who are lower in her social status and turns them into “projects,” meaning she creates opportunities for them to have personality makeovers.
But what makes Clueless one of those ‘90s movies like The Duff is when Cher suffers a backlash of her “personal projects.” In one makeover, she chooses an unpopular girl and dolls her up, only for this person to overshadow her in popularity later on. It doesn’t help that Cher is continually barraged by her older ex-stepbrother as superficial and shallow.
Aside from these small social mishaps, Cher’s life suffers little tragedies which appear catastrophic to her. This impacts on her own identity later on, and affects her confidence immensely. Will she be able to pull out of it? Well, go watch Clueless now and find out! As if!
5. Never Been Kissed
The 1999 comedy film Never Been Kissed is not exactly your average teen romantic movie, since it stars Drew Barrymore as an adult. But she plays Josie, a copy editor sent by her newspaper to do undercover investigative reporting on the current climate of public high schools in America. So she just does that – and pretends to be a high schooler once again for her job.
Now this is where the parallelism starts for Never Been Kissed as one of those funny ‘90s movies like The Duff. As the adult Josie goes back to high school, bad memories of her own excruciating times in high school starts flooding back. Yep, needless to say, Josie is the designated weirdo during her time in high school. She doesn’t have a specific dubious title like “The Duff” but she earns a dubious nickname nonetheless: Josie Grossie.
As Josie Grossie back in high school, she was the nerdy kid who never had real friends. She was very awkward, and was made fun of by the popular kids. Needless to say, she never had any luck with boys.
As the undercover high schooler Josie, though, things soon pick up. In the beginning, she again finds herself as a bit of an outcast. The popular girls of the current school laugh at her, while a more intelligent group of girls befriend her. She also gets a bit smitten with her English teacher, but she can’t blow her cover no matter what happens.
Things turn around for Josie when her boss pressures her to be friends with the popular cliques of the high school instead. The point is to chase story leads where these popular kids apparently conduct themselves in a more rowdy and sexualized behavior. Since that’s juicier a story, Josie heeds her boss’ directives and befriends the popular girls, even dating a popular boy in school.
Will Josie finally belong in high school, with these newer cliques? And will Josie now have better chances of finding love in this space? Watch the movie to find out!
6. 10 Things I Hate About You
This list of movies like The Duff won’t be complete without mentioning 1999’s 10 Things I Hate About You. With a formidable cast like Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt playing the high schoolers in various social circles, it’s sure to become a favorite of viewers in this genre. For younger viewers out there, it’s also a good introduction to the younger selves of these formidable Hollywood actors.
This film is a Hollywood retelling of a classic comedy play by William Shakespeare called The Taming of The Shrew. The plot basically follows the original storyline by the Bard, but now set in a typical American high school. Gordon-Levitt’s character, Cameron, wants to date a certain popular girl in school named Bianca. But seeing that she’s so young, her parents imposed strict date rules for her.
In particular, Bianca’s dad jokingly told her that she can’t go out on a date unless her older sister goes out on a date herself. That could be easy enough, if you think about it. But the catch is, Bianca’s older sister Kat, played by Stiles, is the snarkiest student in their school. Plus, Kat is antisocial to boot. So that’s a huge stumbling block for Cameron and Bianca.
To get around these dating rules, Cameron asks other boys if they want to date Kat. Of course, knowing her shrewish reputation, every guy is put off with her. So Cameron taps one rebel-looking boy in school named Patrick (Ledger’s rebel teen character). Needless to say, the wooing and wacky “courting” begins.
So what do you think happens next? Did Patrick charm the cynical Kat? Was Cameron successful in getting a date with Bianca? Well, get the film and find out!
7. She’s All That
Perhaps the closest ‘90s teen flick to 2015’s The Duff is 1999’s She’s All That. The film stars Freddie Prinze Jr. as Zach, a popular smart student who takes on a bet with his friends when he got dumped by his girlfriend. The bet is, his friends will pick an unlikely girl that he could transform into a prom queen-worthy date.
The friends pick Rachael Leigh Cook who plays Laney, a dorky student who doesn’t have anything in common with the smart jock Zack. However, he still tries his best!
It’s no easy feat to transform someone into a different person in less than two months’ time, but Zach is pressured by his friends. He is also pressured by his ex, Taylor, the one who dumped him. It’s expected that Taylor will become the prom queen of their batch. However, that will be challenged once Laney’s improvements start kicking in.
As an art student, Laney is involved in various artistic projects and performances. It is in these circumstances that Zack tries to get closer to Laney. At first, he tries so hard to befriend her. That’s because she is aware that boys like Zack are not genuinely interested in girls like her. So she tries to throw him off.
However, soon enough, both Zack and Laney become somewhat friends. For Laney’s physical transformation, Zack asks his sister to help her in that department. And this transformation works well for all of them. Taylor is even given a run for her money, when she sees this new “competitor.”
So what do you think will happen next? Will this popular ‘90s film be successful in transforming their version of their duff? Well, watch it and find out! Added bonus: look for the younger versions of Hollywood royalties Paul Walker, Matthew Lillard, and Anna Paquin in this film!