7 best and 7 worst moments in Clueless

Clueless, with all of its best and worst moments, was the feminist teen film we didn’t know we needed. Director Amy Heckerling’s now-iconic film, which debuted in theaters in 1995, surprised viewers with its witty and nuanced dialog, outstanding costume choices, and top-notch acting. Clueless also made stars out of its cast and went on to spawn countless spin-offs and reimaginings, as noted by Town & Country.

Decades later, the smart comedy is still beloved by fans everywhere — many of whom likely wish for access to Cher’s closet to this day. Unlike many other films of the era, Clueless has held up remarkably well, showing just how ahead of its time it was, too. No wonder so many of us are still totally obsessed with it!

When’s the last time you watched Clueless? Did you find yourself looking forward to certain scenes and cringing as you watched others? Well, we sure did. Without further ado, here are the best and worst moments in Clueless.

Best moment: Cher becomes the debate queen

Cher from Clueless wasn’t exactly the best student at Bronson Alcott High School; she often had to argue with her teachers to have her grades raised (cue the moaning of every educator in the country). Nevertheless, she wasn’t without her smarts. “I didn’t want [Cher] to be not intelligent,” director Amy Heckerling told Vice. “I wanted her to just not know what she didn’t know yet.”

That explains why the scenes from Cher’s debate class are some of the best moments in the movie. It’s clear that Cher underprepared for the assignments, but she still makes some pretty great points. When asked by her teacher if all oppressed people should be allowed refuge in the United States, Cher enthusiastically says yes. “And in conclusion, may I remind you that it doesn’t say RSVP on the Statue of Liberty,” she proclaims, to the applause of her peers.

Cher also hits the nail on the head when debating about violence in the media. She argues that there’s no point removing fictional violence from films and television when the news is just as violent itself. We mean, she’s not wrong.

Worst moment: Cher gets mugged and frets about her designer dress

After exiting the vehicle of a creepy classmate, Clueless‘ Cher finds herself stranded in the parking lot of a liquor store in Sun Valley. Naturally, she has to phone a cab to come bail her out and take her home. But before she can complete the call on her cell, she’s robbed at gunpoint. Yikes!

Cher complies with the robber when he demands that she give him her phone, and doesn’t do more than moan when he takes her handbag as well. What’s a bit unbelievable is that she only starts to protest when her assailant demands that she lay face down on the ground. “You don’t understand,” she gasps, revealing her dress to the man. “This is an Alaïa!”

While the line is pretty funny, (and yes, that dress really was an Alaïa), it’s pretty unbelievable that she’d prioritize a dress over her life in that moment. For as clothing obsessed as Cher is, would she really be so cavalier as to try to bargain when there’s a pistol pointed at her? That’s why this scene has to be one of the worst.

Best moment: Ms. Geist and Mr. Hall fall in love

One thing that many fans of Clueless know is that the film was based on the Jane Austen novel Emma, as noted by the Los Angeles Times. Cher’s character is a reimagining of the titular character in the book, a wealthy young woman who lives with her widower father and has a propensity for matchmaking. The parallels are clearly there.

Instead of setting up Mr. and Mrs. Weston as Emma does in the novel, Cher instead takes it upon herself to fix up her debate teacher, Mr. Hall, with the frumpy but endearing Ms. Geist. While the whole thing could have gone sideways, or not have been believable, the chemistry between the actors who play Geist and Hall is totally there. That’s why the scenes of the pair bonding, kissing, and eventually getting married are some of the best in the film. Who doesn’t adore seeing two compatible and genuinely good-hearted people falling in love?

Worst moment: Cher fails her road test

One thing that becomes evident right away in Clueless is that Cher isn’t a very good driver. She’s so bad, in fact, that it prompts Tai to use it as an insult against her, informing Cher that she’s “a virgin who can’t drive.” Way harsh, Tai. But, where is the lie? Cher is so inept behind the wheel that, while it’s indeed comedic, it can give viewers some serious anxiety.

This is especially the case during Cher’s road test, which has the instructor nearly climbing the walls of the vehicle to get out. In the span of a few minutes, a distracted Cher drives under the speed limit and outside of the lines, nearly hits a cyclist while changing lanes, and sideswipes a parked vehicle. 

While you do feel for Cher when she learns that she isn’t getting her much-coveted driver’s license, you may find yourself perplexed at her not understanding just how badly she failed. As such, you were probably nodding in agreement when the instructor calls himself “the messiah of the DMV” for keeping her off of the roads.

Best moment: Tai's makeover

When Cher befriends Tai in Clueless and takes the new girl in school under her wing, she’s quite excited at the prospect of a new “project.” With her flannel shirt and scarlet curls, Tai looks like she just moved to Cali from Seattle, something that Cher decides will not do. That’s right: It’s makeover time — and this makeover is one of the best scenes in the movie.

Rather than strip Tai of her personality and render her just like everyone else, Cher and Dionne work to bring out Tai’s best characteristics. While Cher does rinse out the deep red dye from Tai’s bouncing locks, her hair retains a reddish color. And as one fan remarked, “I love it that they kept her cute curly hair, they always straighten it in makeovers!” By the end of the makeover, Tai is 100 percent feeling herself as she struts in front of the mirror gushing. We are so here for this! 

Worst moment: Cher attempts to seduce Christian

While Cher from Clueless is all about playing matchmaker for other people — which is sometimes successful and sometimes not — she admits that it would be nice to find someone for herself. Despite Cher’s general rule against dating high school boys, our girl was smitten when a handsome guy named Christian strolled into the classroom for the first time.

Almost immediately, Cher puts a plan into action to bag the well-dressed new student. However, for the life of her she can’t understand why he’s not reciprocating her interest; she hadn’t yet realized that Christian isn’t interested in women. It all makes for a pretty awkward scene when Cher finally tries to put the big moves on Christian while they’re laying in bed watching a movie. If only Cher had noticed that he was ogling the handsome eye candy on the screen instead of her. And when she falls off the bed while pushing her hair back? Oh Cher, we are hurting for you!

Once Cher realizes Christian is gay, the two eventually become good friends. But that attempted seduction was one of the worst moments in the film.

Best moment: Cher knows her Shakespeare

While Cher has a seemingly endless stash of clothing and makeup in Clueless, one thing that seems to be in short supply in her room are books. She’s also not one that you’ll find spending hours in the library working on a class project or actually putting in real effort on some extra credit. It’s clear that intellectual pursuits just aren’t really her thing. So when Cher pipes up from the back seat of Josh’s car to correct Heather’s Shakespeare error, it’s not just surprising, but also super funny.

While the quote that Heather recites — “to thine own self be true” — is indeed from Hamlet, it wasn’t Hamlet who delivered the line as Heather had claimed. “That Polonius guy did,” Cher clarifies, thanks to her interest in Mel Gibson’s 1990 film version of Hamlet. Naturally, Heather is mortified, but Josh thinks it’s just as funny as the audience does. For that reason, it’s got to be one of the best moments in Clueless.

Worst moment: Lucy the housekeeper runs from Mel Horowitz

When viewers are first introduced to Mel Horowitz, Cher’s father, in Clueless, it’s clear how intimidating the man is. And while he makes good money as a litigator — a whopping $500 per hour — he’s often gruff and anti-social even when he isn’t working. But, of course, he’s usually working — whether that means reading documents, yelling at people on the phone, or strategizing with others about a case.

However, there’s something unsettling about the scene in which we first meet Cher’s father. As he’s walking down the stairs, the family’s housekeeper notices him and promptly gasps and runs away in fear. “Lucy, our maid, is terrified of him,” Cher explains. 

Look, we get it. It’s meant to be funny, but if you really think about it, it’s unnerving that a woman is deeply afraid of the man who employs her. Can you imagine being scared of your boss? That’s why we think this is one of the worst scenes in Clueless.

Best moment: Cher's dad finally softens up

While Cher’s father, Mel Horowitz, may be rough around the edges and less than sociable most of the time, he does have his moments. They may be uncommon, as most of his interactions with Cher involve him barking at her, but even scary Mel has a softer side.

No more is this apparent than in one of the best scenes in Clueless. In the scene, Cher seeks advice from her father as she’s crushing on a guy (Josh) who she thinks likes someone else (Tai). First, Mel assures his daughter that any guy who doesn’t like her is “a complete moron.” Then he tells Cher that’s she the most gorgeous girl in all of Beverly Hills, admitting he wouldn’t want her to be with anyone who can’t see that. But the sweetest thing Mel tells Cher is that she’s a truly kind person who takes care of everyone around her. “To tell you the truth, I have not seen such good-doing since your mother,” he reveals. Aww! 

Worst moment: Elton refuses to take no for an answer

If there’s one thing that Cher was truly clueless about in Clueless, it’s Elton’s enduring crush on her. It seems that he never missed an opportunity to be close to her, eager to wrap her in his arms, never missing the opportunity to plant kisses on her. So it’s no surprise that Elton persisted in being the one to drive Cher home after a party ended.

As flattering as that might be, Elton’s feelings don’t excuse the way he treated Cher while she was a passenger in his car in one of the worst scenes in Clueless. Upon thinking that Cher had confessed her devotion to him, Elton reaches over to try to make out with her. Confused and frankly not amused, Cher pushes him off, making it abundantly clear that she’s not interested. But that doesn’t stop Elton from repeatedly trying to kiss her, to the point that she gets fed up and exits the vehicle. Way to be a total creep, Elton! 

Best moment: Cher realizes she loves Josh

Throughout the duration of Clueless, Cher spends a significant amount of time complaining about Josh, who’s constantly hanging out at her house. This is in spite of the fact that his mother is no longer with Cher’s father. Homeboy just enjoys spending time at Chez Horowitz — or so it seems.

Toward the end of the film, Cher has a revelation about Josh. While confronting her jealousy after seeing Tai and Josh hanging out together, Cher starts to ask herself questions. After mulling it all over and realizing just how much affection she has for him, Cher realizes that she’s head-over-heels in love with Josh. Suddenly, all of the things that she doesn’t like about him become endearing — even the complaint rock — and that renders Cher terrified.

What is she to do with all of these feelings? How is she supposed to act? Fortunately, Cher doesn’t have to worry, as Josh cares just as much for her as she does him. But she doesn’t know that yet!

Worst moment: Murray is a terrible passenger

Clueless‘ Murray and Dionne are one of the most established couples at Bronson Alcott High School. But that doesn’t mean that their relationship is without conflict, which is evident right out of the gate. And honestly? We’re putting the burden of that on Murray, as he can really be a jerk sometimes.

Take, for example, one of the worst scenes in the movie: when Cher and Murray are riding with Dionne as she learns to drive. First, he laughs at Dionne when she starts her windshield wipers instead of her turn signal, then he yells at her to watch the road. And then he calls her “woman” for the umpteenth time — which Dionne has repeatedly asked him not to do — and tells her that her driving sucks.

After that he totally guffaws at Cher, who’d just confessed she nearly slept with Christian. Murray proceeds to call both Cher and Dionne “b****es.” Top it all off with Murray calling Christian a “cake boy” to explain his sexual orientation and and you have a pretty good idea how lousy Murray was in this totally misogynistic moment! 

Best moment: Cher and Josh finally kiss

After all of the flirtation, footsies, hand-wringing, and staring, Josh and Cher finally acknowledge what Clueless viewers suspected all along: The pair is madly in love with each other. Why else would Josh spend so much time at Cher’s place and go out of his way to pick her up when she was stranded?

The big moment happens after Cher is barked at by one of her father’s associates. She retreats to the stairs, worried that she’s messed up an entire lawsuit. Josh is quick to come find her and does his best to put her at ease. Next, he lets it slip that he finds Cher beautiful and Cher confesses that she cares about him. And then – finally – Josh pulls Cher in for a kiss. After waiting for so long, we finally get to see the arguably best scene in the movie!

Worst moment: Dionne driving on the freeway

While Cher’s driving in Clueless is nothing short of terrible, Dionne’s driving isn’t any better. This was especially apparent in the scene in which Dionne accidentally gets onto the freeway with Cher and Murray as passengers — something she’s clearly never done before — and all hell breaks loose.

First, Dionne accidentally cuts off a truck while attempting to merge, then manages to get flipped off by an elderly couple. Next, a gaggle of motorcyclists come up from behind Dionne’s car and go around it while cutting it extremely close. After that, a giant tractor trailer starts tailgating their vehicle, causing Murray’s life to flash before his eyes.

Fortunately, Murray is able to guide Dionne off of the freeway and the trio are safely able to make an exit — but not before viewers started freaking out too. What an anxiety booster that scene is, making it one of the hardest to watch — and worst — in the entire film!

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