Clueless, Amy Heckerling’s seminal 1995 teen comedy, is beloved as a modern classic for a variety of reasons. Chief among them is Alicia Silverstone’s star-making performance as Cher, the daffy spoiled high school student with bad grades and a heart of gold.
Cher is indeed clueless when it comes to politics and world affairs, but she’s talented at what matters most to her in life: being popular. With Clueless celebrating its 20th anniversary on Friday, here are nine other movie characters who followed in Cher’s steps. On the surface they’re not too bright, but dig a little deeper and it’s clear each is smart in their own, individual ways.
Karen Smith (Amanda Seyfried), Mean Girls
Easily the least well-read of her Plastics high school crew (which is saying a lot), Karen Smith nevertheless stands out for her positive outlook on life, passion for meteorology – she believes her breasts can forecast the weather – and deep, somewhat troubling, love for her male cousin. Played by Amanda Seyfried in her first major breakout role, Karen is a ray of sunshine in a clique whose motives are inherently evil. She’s just too clueless to realize it.
Clueless about: How people perceive her; how evil Queen Bee Regina George really is
Smart at: Forecasting the weather; being a reliable friend; remaining blissfully inside her own head
Shelley Darlington (Anna Faris), The House Bunny
With her droll delivery and ability to play dumb adorably, Anna Faris can turn any role into comedy gold. She does just that in The House Bunny, her first major starring vehicle, in which she plays Shelley Darlington: a nutty aspiring Playboy playmate who through random circumstances becomes a sorority member after getting kicked out of the Playboy mansion.
Clueless about: The proper way to a man’s heart
Smart at: Bringing people together; making young women embrace their sexuality
Romy White and Michele Weinberger (Mira Sorvino and Lisa Kurdrow), Romy and Michelle’s High School Reunion
Best friends for life Romy White and Michele Weinberger haven’t accomplished much, professionally speaking, at the outset of 1997’s cult comedy classic Romy and Michele’s High School Reunion. While initially insecure about where they are in life, after journeying to their 10-year high school reunion in Tuscon, Arizona, the two come to terms with what they thought were their shortcomings and learn to accept themselves for who they are: kooky and fabulous.
Clueless about: How lies can lead to trouble; holding down a job
Smart at: Not caring what people think; improvising on the fly; the rules of friendship
Greg Jenko (Channing Tatum), 21 Jump Street
Greg Jenko is academically challenged (he failed out of senior prom and thinks a “C” grade is worth celebrating), but over the course of 21 Jump Street he proves himself to be one hell of a cop by successfully going undercover as a high school student to take down a drug ring.
Clueless about: Basic academia
Smart at: Fitting in to get ahead
Elle Woods (Reese Witherspoon), Legally Blonde
Blonde, always bubbly and frequently attached to her tiny chihuahua, Elle Woods initially turns off everyone at Harvard Law School after gaining admittance. Through sheer perseverance, she eventually wins over her classmates after demonstrating her surprising and unique intellect.
Clueless about: Gauging how she’s perceived by others
Smart at: Being her true self; the rules of hair care
Natalie Cook (Cameron Diaz), Charlie’s Angels
Natalie Cook is an oxymoron in a gorgeous package. A badass crime fighter for pay who is a befuddling mess when it comes to landing a man, Natalie is both deadly and a bit daft.
Clueless about: The effect her beauty has on men
Smart at: Her job
Katie (Isla Fisher), Bachelorette
Rowdy party girl Katie is a ticking time bomb of neuroses, jacked up on cocaine for much of Bachelorette’s brisk running time. But as played by ace comedian Isla Fisher, Katie is a refreshingly humane comic creation whose insecurities make her hilariously endearing, even when she’s doing very questionable things.
Clueless about: When to quit
Smart at: Keeping spirits high among her friends during the worst of circumstances
Derek Zoolander (Ben Stiller), Zoolander
Possibly the least bright of them all, male model Derek Zoolander prides himself on his manicured good looks and pretty much nothing else. Oddly enough, it’s his massive ego that makes him so thoroughly endearing. Zoolander believes so firmly that modeling is the ultimate profession that he forces anyone he encounters to buy into his delusion.
Clueless about: Everything but fashion
Smart at: Dressing himself
